Penn to Paper: ESPN BETs Big!

On August 8, 2023, ESPN rolled the dice and announced a new licensing agreement with Penn Entertainment. As part of the agreement, Penn will rebrand their existing sportsbook from Barstool Sportsbook to ESPN BET.  Under the terms of the deal Penn will pay ESPN $1.5 billion over 10 years, but the new pact comes with real risk for the Worldwide Leader.  Unlike Barstool Sports, a significant attribute of ESPN’s brand is trustworthy reporting.  If the company’s credibility comes into question, it could undermine both their new venture and a core component of their current business model. 

ESPN’s move into gambling is not the first high profile example of the conflicts of interest that develop when the worlds of sports reporting and sports betting collide.  A couple of months ago, The Athletic’s Shams Charania found himself at the center of a gambling controversy surrounding the NBA Draft.  Shams is an NBA Insider who is often breaks many of the association’s biggest stories.  He also happens to be a paid FanDuel Partner and co-host of “Run It Back” on FanDuel TV.  FanDuel, like rival DraftKings, was built on fantasy sports, but became a major player in the online sportsbook space once sports betting legalization began to take hold in the United States during 2018. 

On June 22, 2023, a little less than eight hours before the NBA draft, Charania reported that Scoot Henderson was “gaining serious momentum at No. 2 with the Charlotte Hornets…”.  As outlined by Sports Illustrated, prior to the report, FanDuel had Brandon Miller at -650 odds and Henderson at +400 odds to be the second player off the board.  After the report, the odds flipped dramatically, making Henderson a -700 favorite and Miller a +400 underdog.  Ultimately, Charania’s reporting failed to align with the outcome of the draft. Miller went #2 to the Hornets and Scoot landed in Portland as the #3 pick. 

Shams’ reporting was very likely legitimate.  It’s not uncommon for there to be internal debate within a team’s front office right up to the deadline to make a decision; however, the potential opportunity to manipulate the betting public so that FanDuel could rack up substantial profits is obvious.  What if Charania had intentionally crafted a false report on the momentum behind Henderson to drive large amounts of losing bets on the number two pick?  That’s not an accusation, it’s a statement to highlight the real issue…The fact that the relationship between the two parties forces us to ASK the question. 

In the aftermath of the NBA Draft controversy, FanDuel claimed that the company, “is not privy to any news that Shams breaks on his platforms”.  Still, the questions were raised, and Shams’ reputation and character were called into question.  These are the treacherous, shark infested waters that ESPN has elected to wade into…

Every Adam Schefter or Adrian Wojnarowski tweet, that potentially influences movement of a point spread or money line, will now come under intense scrutiny.  The truly unfortunate part is that Schefter and Wojnarowski didn’t sign up for this.  ESPN has put them in an impossible position by adding an entirely new dynamic to their jobs.  Yes, their reporting could always move betting lines, but their employer was not previously in a position to benefit from those results. Prior to pursuing this opportunity, executives at ESPN and Disney undoubtedly discussed the public perception of venturing into sports betting and must have asked each other…Is this REALLY WORTH IT???  I believe IT IS!!!

Over the last decade, ESPN’s business has been shifting more and more towards becoming strictly a live rights company.  Studio shows like its flagship program, SportsCenter, just don’t draw viewers the way they use to.  The world has changed and how fans consume sports and sports media has changed significantly.  Sports talk and analysis has been largely democratized by platforms like YouTube and podcast networks.  Sports commentary in between the games has shifted to a market where viewers/listeners are able to choose between the personalities & styles they identify with, across followings large or small.  

The only properties that remain drivers to ESPN’s cable channel are live sporting events, for which, there’s simply no substitute.  The company’s reliance on live rights, and changing consumer preferences, are forcing ESPN to evolve.  Cord cutting and the dwindling draw of studio shows have resulted in declining revenue and a need to cut cost.

Recently, the company laid off several high-profile on-air personalities, including Jeff Van Gundy, Max Kellerman, Suzy Kolber, and Todd McShay.  Having taken steps to reduce expenses, the company will now look for new sources of revenue.  It’s been widely reported that ESPN is believed to be preparing the launch of a full direct to consumer streaming service, either to supplement or replace ESPN+.  Their current streaming service tends to feature lower profile games, with rating drivers like Monday Night Football, remaining exclusive to the cable channel.

If reducing cost and planning a move to a direct to consumer model is step one in ESPN’s evolution, leveraging the brand’s value, that has been built over 40+ years, is step two.  Even as fans no longer look to ESPN for talk shows and commentary in the way that they had in the past, those four letters still hold incredible name recognition and strong brand loyalty.  In looking to capitalize on their branding, the company may have placed the right bet with Penn!

Cultures and customs change over time. Sports betting is becoming a much larger part of the mainstream consumption of professional and collegiate sports.  As such, it’s a seemingly natural fit to integrate the brand most associated with the broadcast of big games with the viewers interaction with those games, through gambling.  Now is the time for ESPN to take its brand in a new direction!

Unlike Barstool, ESPN has a wide enough reach to potentially draw bettors from competing sportsbooks.  Battles will have to be waged with juggernauts, DraftKings & FanDuel, and Penn’s ability to deliver on the tech will be critical, but the partnership could commandeer significant market share. 

The potential conflict of interest concerns will continue to be raised and regulators may intervene at some point.  In the near future, ESPN might have to decide between being a SPORTS NEWS outlet or a SPORTS ENTERTAINMENT platform.  Quite Frankly, it’s probably a shift they should make proactively, as Stephen A Smith is already established as ESPN’s most marketable personality. Doing so could help prevent what currently feels like an inevitable controversy. If the company is slow to act, and its hand becomes forced, the entertainment route is really the only option. It’s not that the “insider” reporting model can’t be monetized, it’s simply nowhere near as lucrative as the opportunity that legalized sports betting presents…

Cash Rules Everything Around Me, C.R.E.A.M.…Get the money!  

Entertainment PAYS!

Playing with Fire, the Phoenix Suns Real Gamble…

At the poker table of professional sports, ownership changes may be the biggest wild cards.  When a team changes hands you never know exactly what the ripple effect will be.  Sometimes new ownership groups come in, almost as silent investors, and do little to alter the day to day operations of the team.  In other instances, a new leadership regime looks to make their mark and establish a new direction.  When it comes to the Phoenix Suns, Mat Ishbia didn’t take long to indicate which category he would fall into.  As Ishbia was nearing the completion of his deal to buy the Suns, ESPN’s Adrian Wojnarowski reported that, “Ishbia is eager to start his involvement with basketball operations and is expected to be a hands-on owner in matters of team building.”  THAT WAS AN UNDERSTATEMENT!!!

Ishbia finalized his purchase, of a reported 57% stake in the Phoenix Suns at a $4 billion valuation, just days before the February 9, 2023 trade deadline.  Somewhere around 60 hours later, the team had traded for Kevin Durant!!!  In order to acquire the 13 time All-Star forward, Phoenix sent forward Mikal Bridges, guard Cam Johnson, FOUR first round picks (2023, 2025, 2027 & 2029), and one first round pick swap (2028) to the Brooklyn Nets.  The massive trade was the very definition of a blockbuster! The timing of deal’s completion, around 12 hours before the trade deadline, meant there would be at least a little time for the dust to settle in the desert.  After the acquisition, an injury limited KD to eight regular season games with the Suns, however, he entered the playoffs healthy and the team had a strong showing.  They defeated the Los Angeles Clippers in first round and pushed the eventual 2023 NBA Champion Denver Nuggets to six games.   

As the calendar turned to the offseason, Ishbia and his team went back to work on further reshaping the Suns.  In the aftermath of the loss to the Nuggets, the team fired head coach Monty Williams.  Williams had helped turn around the struggling franchise which had won an average of just 22 games per season in the four years leading up to his arrival in 2019.  In the four seasons that followed, with Williams at the helm, the team posted regular season records of 34-39, 51-21, 64-18, and 45-37.  His success with the Suns also stretched into the post season, having led the team to a Western Conference Title in 2021, before falling to the Milwaukee Bucks in the 2021 NBA Finals.  Despite a proven track record, Ishbia felt the team needed a new voice.  Approximately three weeks later, on June 6, 2023, the Suns announced the hiring of Frank Vogel as head coach. 

After the coaching change, anyone thinking things would quiet down in the Valley was greatly mistaken.  On June 24th the Suns completed a deal with the Washington Wizards to bring in three time All-Star guard Bradley Beal!  In order to acquire Beal, Phoenix sent guards Chris Paul & Landry Shamet to DC and surrendered even more draft capital.  As part of the trade, Washington received four first round pick swaps (2024, 2026, 2028 & 2030) and SEVEN second round picks!!!  The deal established the foundation of a top heavy, but highly talented roster, featuring Devin Booker, Kevin Durant, Bradley Beal, and center Deandre Ayton.  When free agency opened, the Suns did a great job of filling out their roster with veteran role players who could compliment their new core.  Their free agency class was highlighted by Eric Gordon, Damion Lee, Bol Bol, and Yuta Watanabe, who had played with Durant in Brooklyn. 

After the trades for Durant and Beal, it appeared that the Suns were out of moves that they could make on the trade market.  The team had virtually no draft capital left due to the “Seven Year Rule” which, was established to prohibit the trade of draft picks more than seven years in advance.  Appearances can be deceiving though, as the Suns unexpectedly shaped a couple of unusual NBA transactions.  The first was a trade with the Memphis Grizzlies that brought three second round picks to Phoenix in exchange for two first round pick swaps (2024 & 2030).  The second deal involved the Orlando Magic and resulted in the Suns acquiring three more second round picks in exchange for a first round pick swap in 2026. 

All three of the first round picks involved in these trades were already tied to pick swaps in the Beal trade.  Under these agreements, Washington will maintain the right to swap with Phoenix first, subsequently Memphis/Orlando will have the right to swap with the Suns for whichever pick the Suns have, either their own or Washington’s.  As a result, Phoenix will have the worst of the first round selections between the Suns/Wizards/Grizzlies in 2024 and 2030 and the worst first round pick of the Suns/Wizards/Magic in 2026. 

Ishbia’s background in the mortgage industry clearly influenced the trades with Memphis and Orlando.  In essence, these are draft capital financing agreements.  The Suns are borrowing draft capital, that they can use in trades to acquire players over the next few seasons, in the form of the six second round picks they acquired. Phoenix will pay that capital back, with interest, in the form of swapping into less favorable first round picks in the future.  The structure of these agreements represents a creative solution that will allow Phoenix some flexibility in roster building over the next couple of years; however, it comes at a very high cost.  Phoenix’s position in the first round of the draft for the next seven years is as follows:

• 2024 – Latest Pick of Phoenix/Washington/Memphis

• 2025 – NO PICK

• 2026 – Latest Pick of Phoenix/Washington/Orlando

• 2027 – NO PICK

• 2028 – Latest Pick of Phoenix/Washington

• 2029 – NO PICK

• 2030 – Latest Pick of Phoenix/Washington/Memphis

Mat Ishbia and the Phoenix Suns have redefined what it means to go ALL IN!!!  Now the only question is, will it be worth it?

The city of Phoenix is desperate for a championship.  It’s been 22 years since the Diamondbacks won their only World Series Title. The Arizona Cardinals have just one NFC Title to their name and have never won the Super Bowl. Meanwhile, the Arizona Coyotes are in disarray after nearly three decades in the desert, without so much as a Stanley Cup Final appearance.  The Suns have been the highlight of the region’s professional sports scene in recent years and have won three Western Conference Titles in their franchises history, but never an NBA Title.  Is 2024 or 2025 the year that drought ends? 

There is little doubt that Phoenix will enter the 2023-2024 NBA season as one of the favorites in the Western Conference, but the competition will be tough.  The Denver Nuggets are the reigning NBA Champions and feature a young core of players in or entering their primes.  Nikola Jokić, Jamal Murray, Michael Porter Jr, and Aaron Gordon will certainly have a say in how the Western Conference playoffs unfold. Additionally, the FOUR time champion Golden State Warriors, are still lurking with Steph Curry, Klay Thompson, Draymond Green, and now Chris Paul! Furthermore, a Los Angeles Lakers team led by LeBron James & Anthony Davis cannot be dismissed either.  

The fate of the Suns may come down to the health and availability of Durant and Beal.  After missing the 2019-2020 season recovering from a torn Achilles tendon, KD has played in just 137 regular season games over the course of the last three seasons, an average of 46 per year.  Durant will be 35 years old when the season begins and it’s fair to wonder if he has entered a different stage in his career where he may not be able to return to being a 65+ game player. 

Beal has had trouble staying on the court as well.  After competing in all 82 of Washington’s games during the 2017-2018 and 2018-2019 seasons, he has played in only 57, 60, 40, and 50 games each of the last four years, an average of 52 games per season.  At just 30 years old, Beal is probably the better bet to find his way back to being a consistent night in and night out anchor for the Suns lineup.     

When you consider the injury history, and age in KD’s case, the true stakes of the gamble the Suns have made begin to come to light.  Can this team withstand the grind, and wear and tear, that it will need to in order to successfully navigate four playoff rounds?  What about three?  Perhaps this team is better suited for a run at the newly established NBA Cup, which requires playing a total of seven games to win, rather than four best of seven series.  Would a Western Conference Title or an NBA Cup be enough success to deem the gamble worth it in the eyes of the organization and their fans?  Only time will tell…

The seismic moves made by Phoenix are akin to something out of a sports movie, and I can’t wait to watch it play out. I understand why the Suns were as aggressive as they were in constructing this roster, when you have a title shot, YOU TAKE IT!!! (There was no way Adonis Creed was passing up a title fight with Pretty Ricky Conlan!). Players like Kevin Durant and Bradley Beal don’t become available very often, and when they do, there’s a long line of teams waiting to pounce on that sort of firepower. Unlike Ryan Coogler’s film though, there is no pre-written script to follow in the NBA. Decisions organizations make in team building come with risks, and in this case the real gamble the Suns are taking, is with Devin Booker. 

Booker is 26 years old and has five years remaining on his contract. The Suns had an option to build around their young star player, on his timeline, instead they pushed all their chips to the center of the table now.  Even if the best case scenario plays out for Phoenix, with Durant and Beal remaining healthy, the organization may have limited their championship window with their 26 year old star to the next two seasons.  As Durant ages out of a front-line role, the team will have very few tools at their disposal to add to another star to the roster.  No matter how you look at it, the Suns are playing with fire!    

The NBA Cup Is Happening!

Format

Last week, the NBA officially announced the format for the long awaited In-Season Tournament and it’s going to be AMAZING!  Teams have been designated into six groups of five, with three groups in each conference.  The previous year’s regular season standings were used as part of the group draw to achieve competitive balance. 

Play will commence about ten days into the regular season on Friday, November 3rd and over the course of the month, all 30 teams will play traditional regular season games.  Within their November schedules, teams will play their four group opponents on designated “Tournament Nights”.  These games will count towards both the regular season and group play NBA Cup standings. 

Group winners will be determined by record in games designated for group play.  The primary tiebreaker within a group will be head-to-head results, followed by cumulative score differential, and then total points scored.  Tiebreakers across groups will follow the same procedure apart from head-to-head results.  The winner of each group, along with one wildcard team from each conference, will advance to the knockout rounds. 

The knockout rounds feature single elimination games and begin with the two higher seeds in each conference hosting the two lower seeded teams in intraconference games.  The winners of those games, advance to the NBA Cup Semifinals which will be played in Las Vegas on Thursday, December 7th.  Games played during both the quarterfinals and semifinals will count toward the regular season standings, as these matchups will feature teams that would have played at least three times over the course of a traditional 82 game NBA schedule. 

The winners of the semifinal games will meet in Las Vegas, on Saturday, December 9th to determine the first ever NBA Cup Champion!  The championship game will result in an 83rd game, played by a representative from each conference, that will not count towards the regular season standings.  This approach ensures that each team will continue to visit each NBA city at least once per season and means that one pairing of East/West teams will meet three times prior to the start of the NBA Playoffs, rather than the traditional two meetings.

As the idea of an NBA In-Season Tournament was debated over the last few years, the biggest hurdle was finding the right balance between the new competition and the regular season.  The widely accepted consensus was that the NBA would have to reduce the 82 game regular season schedule to allow for the insertion of tournament games within an already packed calendar.  The solution that the NBA and the NBA Players Association found instead, is nearly perfect! 

Weaving the tournament into the fabric of the regular season schedule only required the addition of a single game and introduces urgency to the early part of the NBA schedule.  The format, and placement within the NBA calendar, should ramp up anticipation for the start of each season and deliver more high-level competition that both fans AND players will enjoy!

Stakes

NBA players love basketball, are extremely competitive, and want to play at the highest levels.  A common criticism of the In-Season Tournament has been, what are the stakes?  Perhaps it is a fair question on the surface but, most of these players want to win at everything they do.  Almost every team has stories of card games, board games, weightlifting challenges, or some other competition they have going on internally. 

A half decade ago the Boston Celtics ping pong games became somewhat of an urban legend in the city with New England Patriots wide receiver Julian Edelman even coming through to take on Gordon Hayward!  Point being, I would be much more surprised with players having an indifferent attitude towards the competition than I would be with hearing stories from across the association about how much teams want to win the inaugural NBA Cup.  For anyone looking for evidence of how competitive the players are…remember the 2022 T’Wolves play-in tournament celebration?

The other aspect that has been raised around the stakes is the question of financial incentive for the players.  Each player on the winning team will receive $500,000.  It’s an amount that is very significant for an end of the bench player but, might not move the needle much for All-Star players making north of $40 million per season.  When you compare the financial incentives to those of winning the NBA Championship though, they are not that dissimilar. 

The NBA playoffs feature a pool of prize money that is awarded to each of the 16 teams that qualify based on a combination of seeding earned and how far they advance.  The 2023 NBA Champions Denver Nuggets received an estimated $7.8 million from the prize pool this past season.  If that money was to be split evenly amongst a 15 man roster, it would result in $520,000 being awarded to each player.  The actual allocation of the NBA playoff prize money is at the team’s discretion, but no matter how you distribute it, financial incentives are not the driving force behind NBA Title teams. The desire to win the championship is! 

The Larry O'Brien Trophy will remain the sport’s greatest prize, as it is presented in acknowledgement of a team earning the title of NBA Champions for a given season.  A goal that organizations have pursued since 11 teams took the court for the 1946-1947 season.  Traditions have to start somewhere, a fact that NBA Commissioner Adam Silver acknowledge in the face of uncertainty surrounding the new competition stating, "New traditions take time. But all throughout sports, we are seeing new innovations, and now is the time for this NBA In-Season Tournament."  It will take time to build a history associated with the NBA Cup however, as we watch the competition unfold, it should not take long for everyone to see that it holds meaning.

The First NBA Cup

Looking ahead to the inaugural edition of the tournament, the scheduling is excellent!  The Tournament Nights in November will all take place on Tuesdays and Fridays, creating a special event feel similar to that of an NFL Sunday, with multiple games underway at once and featured games nationally televised.  The NBA also wisely slotted these nights in between NFL game nights.  While the semifinals will go head-to-head with Thursday Night Football, they set up perfectly for the championship game.  The NBA Cup will be awarded on a Saturday night, unopposed by football, with the College Football Conference Championship games scheduled for the week prior. 

The implications of this new competition are fascinating.  For the first time in the history of the NBA we will see the league’s top teams compete in single elimination games!  Unlike a playoff series where significant adjustments and lineup decisions may take place game to game, coaches and players will be challenged to quickly find solutions on the fly.  The introduction of neutral site games as the tournament nears its conclusion adds an interesting dynamic as well, creating the possibility of raucous crowds with split allegiances.  The environments for those games should be ELECTRIC! 

Additionally, once the first NBA Cup has been won, we will be faced with two new possibilities.  The first is the concept of a “Double Champion”.  In the early years, we won’t have a historical precedence to compare to but, we may see a team win both the NBA Cup and the NBA Championship in the same season!  The second scenario would be even more captivating…the possibility that the NBA Finals could be a REMATCH of that seasons NBA Cup Finals!!! 

Imagine both teams vying for the sport’s ultimate prize, with one team pursuing what figures to be an elusive double championship season, while the other team is looking to avenge a Cup Finals defeat.  The potential storylines are endless…Get your popcorn ready, this is going to be fun!

Name / Names?

OK, if there is one thing I’m not exactly amped for, it’s the name or names…The trophy is being called the NBA Cup but, the official releases from the NBA still refer to the “In-Season Tournament” as well.  I always thought In-Season Tournament was just a placeholder until the details were finalized. 

My hope is that In-Season Tournament is just something that the league felt they needed to keep front and center in their marketing campaign for the first year. The goal in doing so would be to help educate viewers and draw attention to the fact that a new competition is being added to the calendar.  After year one, it needs to go!  In-Season Tournament feels about as clunky as renaming the playoffs as the After-Season Tournament.  Brand the entire competition as the NBA Cup Tournament or simply the NBA Cup. 

Also, the NBA Cup name probably needs to be rethought at some point as well.  It’s fine but, NBA Cup Champions and NBA Champions are too similar for my liking.  There are so many other options!  In working through all the details of the tournament and the CBA did they just forget to name this thing?  Commissioners Cup, Players Cup, Association Cup, World Cup (sorry, that one’s taken!), North American Cup, Naismith Cup…you get it. 

Future

The NBA Cup will likely evolve over time.  I expect to see changes made to the format over the years, just as we have seen with the NBA playoffs throughout history.  Feedback from fans, players, coaches, team execs, etc. will be considered but, the initial format is very well constructed and there are three core elements that I believe will stand the test of time. 

The first being group play games counting towards both the NBA Cup and the regular season standings.  Aside from how well this works with the schedule, it serves the purpose of integrating the NBA Cup into the season, rather than having it exist as an entirely separate entity.  NBA seasons will now see an NBA Cup Champion crowned, in addition to Eastern & Western Conference Champions, and ultimately an NBA Champion.

The second element that I believe is here to stay is the use of single elimination games in the knockout rounds.  The format significantly differentiates the tournament from the playoffs, which is very important to its success. 

And finally, the third element that I believe the NBA nailed is the use of a neutral site.  I’m not suggesting that the NBA Cup will grow to anywhere near the level of interest of the Super Bowl but, it creates a unique opportunity to allow the NBA world to descend on a single location for a championship weekend, which should be a fantastic experience for fans. 

While I expect the neutral site to remain, it will be interesting to see if the NBA Cup moves to other locations in the future.  Las Vegas feels like the perfect setting to host the early years of the event but, as the NBA seems destined to expand to the city in the not-too-distant future, the event may need to be moved to guarantee a neutral site. 

One possibility is that it remains in Vegas, just as the Super Bowl is always hosted in an NFL city, with the possibility of the host city’s team advancing to that stage.  Once there is an NBA franchise in Las Vegas, the tournament could also go on a Super Bowl like rotation between NBA cities like Los Angeles, Miami, New York, and San Francisco. Alternatively, the tournament could move to another full-time neutral site host city, such as San Diego where Stan Kroenke is building a new 16,000 seat arena.  

Lastly, one thing that cannot be ruled out, as the NBA looks to continue to grow its brand, is the idea of taking the tournament overseas to host cities in Europe such as London, Madrid, Paris, Rome, or Milan. If there is one thing we have learned about Adam Silver, it’s that he’s not afraid to explore new territory!

Dame’s Time

Halloween night 2012, Damian Lillard stepped on the NBA scene for the first time.  Making his debut with the Portland Trail Blazers, Dame delivered a 23 point and 11 assist performance in front of a sold-out Rose Garden.  When the final buzzer had sounded, the number 6 pick in the 2012 draft had helped lead his team to victory over the star-studded Los Angeles Lakers, who had received a combine 63 points from Kobe Bryant & Dwight Howard. 

Lillard would go on to play all 82 games of his rookie campaign, averaging 19 points and 6.5 assists, in what was an uneven season for Portland.  The team finished 33-49 with the fanbase enduring a 13 game losing streak to end the season.  Despite the finish to the year fans in the Pacific Northwest went into the summer with the belief that they had struck gold in the draft and found a future star to pair with franchise cornerstone LaMarcus Aldridge…and they were RIGHT!

The following year, in only his 2nd season, Dame was named an NBA All-Star.  Over the course of the next two seasons the Trail Blazers won a combined 105 regular season games and advanced to the playoffs each season. The core of a championship team appeared to be in place with the duo of Lillard and Aldridge complimented by Wes Matthews and the promise of a sharp shooting guard taken with the 10th pick in the 2013 draft, CJ McCollum. 

Despite the potential this roster possessed, the regular season success failed to translate to the post season where the team won just one playoff series over the course of those two seasons, a 2014 six game triumph over the James Harden & Dwight Howard led Houston Rockets.  That series is remembered most for Lillard’s series clinching three at the buzzer of Game 6.  The 2014 team would fall to the eventual champion San Antonio Spurs in the Western Conference Semifinals while the 2015 team was derailed by a late season injury to Matthews and eliminated in the first round by the Memphis Grizzlies, both five game defeats. 

Dreams of an NBA title were quickly met with a harsh reality in July of 2015 when Aldridge decided to look outside of the organization for a path towards post season success and Portland declined to offer Matthews a contract.  In free agency, Aldridge signed with San Antonio and Matthews inked a lucrative deal with the Dallas Mavericks despite being in the midst of recovery from a torn Achilles tendon.  At 25 years old, entering his 4th season, the Portland Trail Blazers were clearly Dame’s team.  The weight of an entire region’s championship aspirations was placed squarely on his shoulders and for the next 8 seasons, he did more than his part to realize those dreams.    

In his first season as the face of the franchise, Lillard established new career highs in both points (25.1) and assists (6.8). To the surprise of many, aided by the emergence of McCollum, he led the Trail Blazers to a respectable 44-38 record.  Portland entered the 2016 playoffs as the 5th seed in the Western Conference and matched up against the heavily favored “Lob City” Clippers.  Los Angeles was led by the trio of Chris Paul, Blake Griffin, and DeAndre Jordan. 

The series started off as many expected, with the Clippers winning the first two games at home by 20 and 21 points, respectively.  When series shifted to Oregon for Game 3, the world got its first real glimpse into Portland’s future as we watched CJ’s 27 points, be topped only by Dame’s game high 32, in a 96-88 Portland victory.  The series turned in Game 4 when LA lost both Paul and Griffin to injuries that would end their seasons, a blow that was too much for the veteran Clippers team to overcome as they fell to the Trail Blazers in six games. 

Portland would go on to lose to the defending champion, and record setting, 73 win Golden State Warriors in five games however, the Western Conference Semifinals appearance gave the Trail Blazers reason to believe in their future.  Lillard averaged 31.8 points and 7.6 assists in the five game contest and McCollum proved ready for the stage averaging 21.4 points. Dame’s performance was highlighted by a 40 point and 10 assist Game 3 Portland victory in which he connected on 8 of 13 shots from beyond the arc!  One year removed from the foundation shaking departures of Aldridge and Matthews, there was once again reason for optimism heading into the offseason.

The 2016 offseason came and went without major changes but, hope remained that the team could build off their surprise success of the previous year.  Instead, Portland looked more like the team many expected to see in the aftermath of the 2015 offseason.  As mid-February rolled around, the team had lost 4 of 5 and found itself 9 games below .500 at 23-32.  Looking for a spark, Portland swapped centers with Denver in a deal that resulted in Mason Plumlee and a 2018 2nd round pick going to the Nuggets and Jusuf Nurkić landing with the Trail Blazers along with a 2017 1st round pick. 

Nurkić played well down the stretch run appearing in 20 of 27 games while averaging 15.2 points, 10.4 boards, and 1.9 blocks and Portland rallied to finish the regular season at 41-41.  The team’s late season push was enough to grab hold of the 8th seed in the Western Conference.  Unfortunately for the City of Roses, their reward for making the playoffs was a rematch with the Golden State Warriors who had added Kevin Durant.  The Warriors made quick work of the Trail Blazers, authoring a four game sweep to start their post season march towards a 3rd straight Western Conference Title and their 2nd NBA Title in the past three years. 

Portland’s big swing of the 2017 offseason took place on draft night when they sent the 15th and 20th picks to Sacramento in exchange for the 10th pick.  With the tenth pick, the team selected Gonzaga big man Zach Collins, passing on the opportunity to draft Kentucky big man Bam Adebayo who went 14th to Miami.  At the time, Collins was believed by most evaluators to have the highest potential to develop into a complete NBA center however, the Trail Blazers could have greatly benefited from adding Bam’s defensive versatility. 

When the regular season came around, the team looked to replicate the late season success they had in the year prior.  Nurkić picked up where he left off averaging 14.3 points and 9.0 rebounds, and the tandem of Lillard & McCollum continued to deliver with remarkable consistency.  The team once again seemed to be building towards contention, finishing the regular season at 49-33.  Their regular season performance earned them the Western Conference’s #3 seed, home court advantage, and a matchup with the 48 win New Orleans Pelicans.  Virtually everyone expected a long series but, Lillard slipped into a shooting slump at the wrong time and the Trail Blazers had no answers for Anthony Davis and Jrue Holiday who led the Pelicans to a four game sweep. 

After the disappoint of the New Orleans series, Portland’s front office continued to make tweaks around the edges of the Trail Blazers roster.  In July of 2018, the team signed shooting guard Seth Curry to a 1-year deal after the three point specialist had missed the entirety of the 2017-2018 season with a stress fracture in his left leg that ultimately required surgery.  The team continued to add throughout the season signing center Enes Kanter in February, after he was waived by the New York Knicks, and making a deadline deal with Cleveland to land forward Rodney Hood.  The acquisitions provided depth at positions of need for a Portland team that was looking to climb the Western Conference standings. 

The Trail Blazers entered the All-Star break at 34-23, after a win over Golden State, and closed the regular season on a post break 19-6 run to finish at 53-29 and qualify for the playoffs as the conference’s #3 seed.  Now 7 years into his NBA career, Lillard had put together his best season to date.  He had established career highs in assists (6.9), assist to turnover ratio (2.56), and effective field goal percentage (52.2%) while averaging 25.8 points.  Dame also played 80 games during the regular season, the most he had appeared in since he competed in all 82 of Portland’s contests in each of his first three seasons. 

Portland began the 2019 playoffs, once again, with a difficult opponent in their #3/#6 matchup.  In order to win their first playoff series in three years, Lillard would need to lead his team past the 49 win Oklahoma City Thunder.  OKC featured a dynamic duo in Russell Westbrook & Paul George and an intimidating paint presence in Steven Adams.  The Thunder had won all four meetings with Portland in the regular season and, if the circumstances weren’t challenging enough already, Portland had lost Nurkić to a late season injury forcing Kanter into a starting role.  Kanter turned out to be up for the task and the two teams played a competitive and entertaining series in which the first and the final games of the series would end up being the most tightly contested down the stretch. 

In Game 1 Paul George struggled to find his shooting stroke going 8/24 but, hit a three pointer with under three minutes to play to pull the Thunder within one at 93-92.  Lillard immediately responded, and in what would foreshadow things to come, hit a 30 foot trey on the next possession to stretch the Portland lead back to four, ending the Thunder’s rally. 

The teams split the next two games with the home teams holding serve.  The Trail Blazers had rode a 33 point night from McCollum to a 20 point victory in Game 2 which was countered three nights later with a 33 point performance by Westbrook in a 12 point Thunder win in Game 3.  With the Blazers holding a 2-1 edge in the series, Portland sought to take Game 4 and return home with a chance close things out.  Dame’s team was able to do just that as Lillard scored 15 points in the 3rd quarter to extend a 4 point halftime lead to 11, which proved to be too much for the Thunder to overcome despite a 32 point effort from George. 

As the series shifted back to Oregon, fans packed the Moda Center ready for a celebration.  Portland’s first playoff series win in three years was within reach but, the cliché that close out games are always the toughest, held true.  Lillard came out firing with a 34 point first half but, George knocked down eight of his ten first half shots and racked up 20 points of his own.  Oklahoma City hung in the fight trailing only by one at the half, 61-60. 

Portland continued to look to pull away in the 2nd half and for a moment, appeared to have.  Dame drained a step back three to put the Trail Blazers up 84-75 with 3:29 to play in the 3rd quarter.  The home crowd to had to feel as though victory was within the Blazers grasp however, the Thunder simply would not fold.  Oklahoma City quickly turned a late 3rd quarter nine point deficit into a FIFTEEN point 4th quarter lead! 

With 7:12 remaining in the game and Thunder up 107-92, it looked like a certainty that the series would head back to the Mid-West for a Game 6 and that the capacity crowd would head home disappointed.  In the face of those long odds, Portland refused to back down and the emotional roller coaster ride continued as the home team did not let the 24 point swing dishearten them.  Over the next 6:15, the Blazers went on a 21-6 run, with 10 points from forward Maurice Harkless, to tie the game at 113 with 57 seconds remaining…What happen next remains one of the most remarkable finishes in NBA history! 

Paul George broke the tie with a 15 foot jump shot over CJ McCollum with 39 seconds left only to watch Lillard make a driving layup 7 seconds later following a Terry Stotts timeout.  Lillard had been defended by Dennis Schröder and after beating him off the dribble somehow managed to split Paul George and Jerami Grant, who had collapsed to meet him at the rim. The game was tied at 115 and the decision by Lillard’s long-time coach to go quick, put Portland in position to have one last possession to either tie or win the game. 

On the ensuing Thunder possession, Westbrook went to the rim but was defended well by Al-Farouq Aminu.  The forward, who had been a solid contributor in his 4 years with Portland, contested Westbrook’s shot attempt, forcing a miss, and gathered the rebound.  With 17 seconds remaining, Aminu handed the ball off to Dame who dribbled about five feet past half court and assessed his options.  Stotts had one time out remaining but, rather than calling it to draw up a play he left the game in his star’s hands. 

Instead of running any sort of action, Portland spaced the floor and cleared out for Lillard to go one on one with George who had stepped out to establish his defensive position about 30 feet from the basket. As the clock wound down under four seconds, Lillard had still only drifted a few feet closer to the basket from half court.  With everyone in the building expecting Dame to put the ball on the floor and drive, he took one step and pulled up from 37 feet, well out of the reach of George’s contest. The high arcing shot left Lillard’s hand with approximately 1.6 seconds left but, it felt as though time stopped as the shot reached its apex and transitioned into its descent toward the rim.  As the red light around the backboard illuminated and the buzzer sounded, Dame’s hail marry shot passed through the cylinder and the arena erupted! 

In the immediate aftermath, as Lillard’s teammates ran to mob him in celebration, Dame still looking locked in as ever, waived goodbye to the Oklahoma City Thunder.  That last shot by Dame gave him 50 for the night, a new franchise playoff record, and added him to a list accompanied only by Michael Jordan as players with multiple series ending buzzer beaters.  Rip City was rolling into the Western Conference Semis!

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The West’s second round brought a very different challenge in the #2 seeded Denver Nuggets.  Denver was coming off a seven game first round victory over LaMarcus Aldridge’s San Antonio Spurs after completing a 54-28 regular season.  The Nuggets had missed the playoffs the previous year but, the emergence of a couple of young players had vaulted them into the upper echelon of the Western Conference.  At 24 years old, center Nikola Jokić had averaged 20.1 points, 10.8 rebounds, and 7.3 assists during the regular season.  His running mate, 22 year-old guard Jamal Murray, had establish career highs of his own at 18.2 points and 4.8 assists. 

For the first time, a Lillard lead Trail Blazers team entered a playoff series as the more experienced team.  They had gone from the hunter to the hunted.  One similarity to Portland’s first round opponent was that the Nuggets, like the Thunder, held the edge in the regular season head to head matchup.  Denver had taken three of four from Portland and those games proved to be significant. One game separated the two teams in the regular season standings which meant that the series would open up at altitude in the Mile High City. 

As the series tipped off, Damian Lillard carried over his hot shooting from the first round.  In Game 1 he hit 12 of 21 shots for 39 points but, Jokić had 37 points of his own on 11 of 18 shooting and the Nuggets pulled out a 121-113 win.  Game 2 could not have possibly looked more different.  Both team struggled mightily on offense with Portland shooting 42.4% and Denver shooting an abysmal 34.7%.  A 23-7 edge in offensive rebounds kept the home team in the fight but, a game high 20 points from CJ McCollum was enough for the Trail Blazers to pull out a 97-90 win and send the series back to the Left Coast even at a game apiece. 

Game 3 must have been an excruciating viewing experience for fans of each of these teams.  With 35 seconds left in the 4th quarter, Lillard had the ball with the score tied 100-100.  Dame drove past Murray and made a floater over the contest of Paul Millsap to give Portland a 102-100 lead with 31 seconds remaining.  At the other end, after a Michael Malone time out, Will Barton inbounded the ball to Jokić and immediately cut to the rim.  Jokić delivered a perfect pass with Lillard trailing and Barton was able to make an up and under layup to tie the game at 102 with 28 seconds left. 

On the following Blazers possession, Dame drove to the paint and drew three defenders. With about 9 seconds remaining he kicked the ball out to a wide open Aminu who fired up a three pointer with three seconds left on the shot clock and just under eight seconds remaining in the 4th.  The shot ricocheted off the back rim and was rebound by Murray with 4.4 on the clock.  Unable to successfully push the ball up court, the Nuggets called a time-out with 1.8 seconds remaining.  No longer allowed to advance the ball, Denver attempted a long inbound pass that was intercepted by Harkless who attempted a 60 foot heave that fell short.  The game was headed to overtime!   

The scoring in the extra session was opened by a Murray driving floater, 104-102 Denver.  McCollum countered with an 18 foot jumper just under a minute later, tied again.  43 seconds later, another McCollum jump shot fell, this one from behind the arc, 107-104 Portland.  49 seconds later Murray countered with a three of his own, tied again.  A Millsap layup with under a minute to play put Denver back on top at 109-107. 

The score would remain that way until Lillard stole the ball from Torrey Craig with 17 seconds left and began racing up the floor.  With 14 seconds left Dame tried to sidestep around Millsap and attempted a layup but, failed to convert.  The shot attempt didn’t contact the rim and as it came down was deflect by both Lillard and Millsap and the ball careened toward the Nuggets bench.  Aminu, who had run the floor with Lillard, reacted quickly and secured the rebound then passed the ball to a trailing McCollum who drove and drained a floater for his third basket of the period to tie the game once again.  After a Denver time out, Jokić missed a three at the buzzer, the game was headed to DOUBLE OT!! 

Lillard opened the scoring of the next session with a 20 foot jumper and, after the teams traded baskets, hit a deep three to put the Blazers up five as the clock ticked toward the half way mark of the period.  Denver responded with Jokić assisting on a Barton three and a Millsap two from close range, tied again! McCollum added his 2nd bucket of the 2nd extra session with 1:27 remaining but, Gary Harris responded with a driving spin move that resulted in a layup to tie the game yet again with 1:03 remaining…

The two teams remained scoreless over the next minute.  Lillard attempted to break the scoring drought with a tough step back three over Gary Harris but, his shot came up short, landing on the front rim and bouncing out.  At this point, fatigue had clearly set in for both teams but, once again the game clock needed to be reset to 5:00, we were headed to TRIPPLE OT!!! 

McCollum opened the scoring of the third overtime with a two point jumper that was quickly answered with a Harris three, 121-120 Denver.  CJ then responded with a long step back two followed by a three, 125-121 Portland.  The Nuggets then went on an 8-0 run over a two minute stretch to go up 129-125 with only 32 seconds to play…timeout Portland. 

Following the TO, Harkless inbounded to Lillard who drove by Craig.  After inbounding the ball Harkless had drifted towards the corner and drew Millsap with him, creating enough space and keeping Millsap far enough away from the rim that he wasn’t in a position to help on Lillard without fouling.  The result? An uncontested layup to put Portland back within two with 27.3 seconds left on the clock. 

What came next? More McCollum heroics only this time on the defensive end.  As Murray brought the ball across half court, along the sideline opposite the benches, CJ blanketed him and reached in behind Murray’s back with his left hand swiping at the ball and knocking it loose.  As Murray tried to maintain his dribble, the ball deflected off his fingertips and out of bounds! Blazers ball!

On the ensuing possession, Denver began with Murray defending Dame but switched Craig onto him with about 12 seconds on the clock.  Once again, Lillard drove and beat Craig off the dribble and Harkless had again drawn Millsap to the corner to defend the three point line.  Jokić may have been in a position to contest but, wasn’t fast enough to react and was sealed off by Kanter.  Dame laid the ball off the glass and in against a late contest by Craig who had recovered quickly.  With 8.4 seconds remaining the game was tied again! 

On the next possession, Jokić set a great screen that forced Kanter to switch onto Murray.  Despite having the matchup they were looking for, the Nuggets were unable to capitalize as Kanter managed to stay in front of Murry, cutting off his driving lane, and forcing him backward.  With time winding down, and Murray having retreated towards half court, he had to resort to taking a deep three from the “d” in the Moda Center logo.  The shot banged high off the backboard and then caught the front rim bouncing harmlessly out.  Yet again, the clock was reset to 5:00, we were heading to QUADRUPLE OVERTIME!!!! 

At this point, the crowd is feeling fatigued, what the players are going through is indescribable.  The first four minutes of the 4th overtime period were played to a 4-4 tie, evening the game at 133.  What was most significant is that it was Rodney Hood who tied the game for Portland with 1:07 on the clock.  Hood had been on the bench for 17 minutes and 30 seconds of the 18:01 of extra time that had been played when he checked in with 1:59 on the clock. 

With 1:00 remaining, McCollum committed a shooting foul and Barton made one of two free throws re-establishing a slim Denver lead, 134-133. Needing to respond, Hood came through for Portland again, making another two point jumper with 44.9 seconds left, 135-134 Portland. 

At the other end, directly in front of the Trail Blazer bench, Millsap had a one on one opportunity in the low post against Aminu.  In the span of two left-handed dribbles, Millsap gained position leaning his right shoulder into Aminu’s chest and curled toward the basket taking a five foot shot with his left hand.  The ball landed softly on the front rim bouncing towards the cup, then it caught the back rim and bounced again, continuing its forward momentum to reach the back board, another bounce off the glass changed the ball’s direction back towards the cylinder and after glancing the back rim again, the ball fell through the net, 136-135 Denver with 27.6 on the clock…timeout Portland. 

Following the timeout, McCollum thought he had an opportunity to drive on Jokić but, didn’t see the trailing Malik Beasley.  As CJ pulled up for a mid-range jumper, the Nuggets defensive quickly collapse on him, and his contested shot missed off the back rim.  Despite the contest, McCollum tracked the ball the entire way and when the rebound came back out in his direction, he somehow managed to jump up and secure the ball over a crashing Torrey Craig.  Almost in a single motion, he kicked the ball out to Hood before his feet touched back on the floor.  Hood calmly caught the pass and pumped fake a desperate close out attempt by Barton.  After watching Barton leave his feet and sail by, Hood took one dribble and then raised up from beyond the arc, nothing but nylon! Hood was now three for three in the period and Portland had a 138-136 lead with 17.8 remaining on the clock. 

After a Denver timeout, Jokić attempted to post up Harkless who did well to hold his ground and prevent an easy look at the rim.  Unable to move Harkless, Jokić made a spin move and took a wild shot with 5.6 seconds remaining.  The shot missed badly but, Harkless was called for a shooting foul.  Jokić missed the first free throw ultimately sealing Denver’s fate. 

After Jokić made the second free throw, Denver fouled Seth Curry who made both of his free throws with 2.8 remaining to put Portland up 140-137.  Out of time outs, the Nuggets attempted one last desperation inbound pass that traveled past half court but, it was intercepted by McCollum and the clock hit zero, this time it would not need to be reset to 5:00, Portland had secured a 2-1 series lead. 

To call Game 3 the CJ McCollum game would not being doing justice to all the wild endeavors that took place over 68 minutes of NBA playoff basketball however, it was definitely one for the resume and for anyone who doubted CJ as a worthy partner in crime for Dame.  McCollum scored 18 of his game high 41 points after regulation had ended!  Maybe more importantly, the team trusted him as he attempted a staggering THIRTY NINE shots!  That was seven more than Jamal Murray and 15 more than Lillard. 

The game was the first, and remains the only, NBA playoff game in the shot clock era to extend to a fourth overtime period and only the second all time.  The other being a series clinching Game 2 victory for the Boston Celtics over the Syracuse Nationals in the 1953 Eastern Division Semifinals. 

Portland was now 4-0 at home in the playoffs and had won 12 straight at home dating back to the regular season.  Entering Game 4 and looking to extend that winning steak to take a commanding 3-1 lead in the series, many people from analysts to fans, liked Portland’s chances.  The natural tendency in the aftermath of a game like Game 3 is to assume that the heartbreak of being on the losing end is almost too much to bounce back from.  If that is truly the case, then someone forgot to inform the Nuggets. 

Game 4 was tight throughout with Portland jumping out to a six point half time lead but, Denver came out strong in the second half with a 27-14 3rd quarter that would tip the scales in their favor.  Jokić delivered an 8/15 shooting performance on his way to a 21 point, 12 rebound, and 11 assist night that helped lead Denver to a 116-112 win which leveled the series at 2-2. 

With the series shifting back to Denver, the Nuggets came out firing on all cylinders in Game 5 while the Trail Blazers struggled shooting from everywhere; 36.7% from the field, 27.0% from three, 53.3% from the free throw line.  A six point first quarter deficit quickly ballooned to 18 at the end of the 2nd quarter and the Blazers wouldn’t get any closer after halftime falling 124-98.  Now down 3-2, Lillard’s team now found themselves trailing in the series for the first time since the Game 1 loss. 

If the Trail Blazer’s were going to return to Denver for a seventh game, they were first going to need a big response back at home, and they got it from their exceptional backcourt pairing.  Dame and CJ combined for 62 points on 23 of 47 shooting, which included Lillard’s 6 for 13 performance from three.  The result was a 119-108 Trail Blazers victory and a series knotted at 3-3. 

Although nothing could compare to what transpired in Game 3, you never know what to expect heading into a Game 7.  Coming off a hot shooting performance in Game 6, Lillard surprisingly struggled to find his stroke and the Nuggets jumped out to a 29-17 lead at the end of the first quarter.  Dame’s shooting struggles would continue throughout most of the game as he ended up just 3/17 but, found other ways to contribute.  The Blazers star made five of six free throws on a 13 point night, relied heavily on his play making ability racking up eight assists, and secured ten defensive boards. 

Fortunately for Portland, McCollum’s hot shooting from three nights prior only got hotter as Portland knocked the Nuggets lead down to one, entering the 4th quarter.  Dame saved his best for last making two of his three 4th quarter three point attempts while CJ would put the finishing touches on the most important performance of his career. 

McCollum shot 17 for 29 on his way to 37 points, including making Portland’s last three field goals of the game.  The last of those buckets, a 16 foot pull up over Craig, came with 12.4 seconds remaining and extended the Blazers lead 98-95, a lead they would not relinquish!  After adding a couple late Evan Turner free throws the Trail Blazers would leave Denver with a 100-96 win, 4-3 series victory, and a berth in the Western Conference Finals!  Game 7 WAS the CJ McCollum game!

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The run up to the 2019 Western Conference Finals was the peak of Lillard’s Trail Blazers run.  The third round of the playoffs saw Portland clash with a familiar foe in the Golden State Warriors.  The Warriors were without Durant due to an injury suffered in the previous round vs Houston but, the two time defending NBA champions still had their now veteran trio of Stephen Curry, Klay Thompson, and Draymond Green. 

Curry showed up and showed out in the series averaging 36.5 points on 46.9% shooting along with 8.3 rebounds and 7.3 assists, leading the Warriors to a four game sweep and their 5th straight Western Conference Title.  Games 2 and 4 came down to the wire, with Game 4 going to overtime, but Golden State was simply too much for Portland to handle.  Once again, the Blazers were headed into the summer looking for answers.

Over the next two seasons Portland looked to add veteran players who could compliment their backcourt duo.  Most notable was the signing of Carmelo Anthony in the summer of 2019.  Melo would spend two years in Portland and provided a consistent wing scoring option that the Trail Blazers had lacked throughout Lillard’s career.  Despite the added fire power on offense, the team continued to lack necessary defensive versatility and failed to replicate the success of the 2019 run in the 2020 and 2021 playoffs. 

The 2020 season was halted in March due to the onset of the COVID-19 pandemic and when play resumed in the Orlando Bubble in late July, Portland qualified for the playoffs as the Western Conference’s #8 seed only to fall in five games to the eventual champion Los Angeles Lakers, led by Lebron James and Anthony Davis.  The 2021 team qualified for the playoffs as a #6 seed after a 42-30 season that was abbreviated due to the on-going pandemic.  They would match up with the Nikola Jokić led Denver Nuggets for the second time in three seasons.  Denver had lost Jamal Murray to a torn ACL but, now featured Aaron Gordon and an emerging young talent in Michael Porter Jr.  A hard-fought series ultimately went to the Nuggets in six games and the Trail Blazers front office decided it was time for a new direction, parting ways with head coach Terry Stotts, in what was announced as a mutual agreement. 

In hindsight, the departure of Lillard’s head coach for all nine of his seasons in Portland was really the beginning of the end.  It signaled that the Trail Blazers front office was looking to shake the foundation of the team up to explore alternative avenues and timelines towards contention.  Chauncey Billups was hired as head coach prior the 2021-2022 season, a season in which Lillard would be limited to just 29 games due to injury. 

With the team struggling and the trade deadline approaching, Portland decided to trade CJ McCollum to the New Orleans Pelicans. The deal was mostly to clear salary from the books heading into the summer and returned one potentially significant asset in a protected 2022 New Orleans first round pick.  The pick would convey to Portland if it landed anywhere from picks 5 through 14 and New Orleans was 10th in the Western Conference standings at the time of the deal.  If the Pelicans failed to qualify for the playoffs, it was very likely the pick would convey to Portland. 

Unfortunately for the Trail Blazers, McCollum helped the Pelicans climb to 9th in the standings and qualify for the play in tournament.  He then scored 32 points against San Antonio and 19 against the Los Angeles Clippers to help New Orleans advance to the playoffs, ensuring that the Pelicans pick would not convey to Portland.  Instead, Portland would receive a 2025 first round pick from Milwaukee.  Meanwhile, with Dame sidelined and CJ no longer a part of the team, the losses piled up.  The team went just 2-21 after the All-Star break and finished with a 27-55 record in their first year with Billups behind the bench.

Regarding the trade of his long-time co-star, Lillard had the following to say in the wake of CJ’s departure:

“We talked about it over the years, like, this being a possibility.  We both knew that this point would be coming. But that don't make it no easier to deal with. I think that's where I am now. Me and him literally talked about it happening, the possibility of it and it was likely and stuff like that, and I still woke up this morning like, sad. It's actually done.”

“When I'm seeing 'CJ To The Pelicans' and stuff like that, it's like damn, ain't no coming back from this, this is it. It ain't gonna be no every day, pull up to the house, dinner on the road, all that stuff. It's done, he's on a new team. As much as I understood it and he understood it and we kind of have always communicated in a transparent way, it don't make it any easier to deal with or to look at. Like man, is it really over? Is the run really over?”

“I think we'll be remembered as trouble. We never won a championship together, we never played in the Finals together, but we have always been a winning team. Us together, we've always been a winning team, we've always been a playoff team, so we never had empty success in games. We've always won games ... we just didn't win at the highest level.”

“No matter if it was the best team in the league, worst team in the league, they knew that they had trouble. And in the playoffs -- people can say what they want -- we've had our down moments in the playoffs and we've had high moments in the playoffs, I would say about split.”

“Regardless of that, we were always the team that people would prefer not to play in the playoffs, regardless of any of that, because they knew they had trouble. That's how I think we'll be remember is like man, when CJ and Dame was together for that eight, nine years, trouble. I think that's how we'll be remembered.”

The run really was over.  The duo that Dame dubbed Trouble had led the Trail Blazers to three playoff series victories after Aldridge left the organization.  Over the course of the previous six seasons (’15-’16 through ’20-’21), they had guided Portland to a 264-210 (.556) regular season record.  Under their watch, Portland was always in the mix and seemingly one piece away from having a team with a real shot at an NBA title.  Unfortunately, Portland’s front office was never able to deliver that final piece to the puzzle.  

After the 2022 season speculation that Lillard would ask for a trade to a more competitive situation was rampant but, Dame remained committed to trying to find a way to bring a title to Portland.  In the 2022 offseason, the Trail Blazers took one last swing at trying to retool the roster around Lillard.  They traded the 2025 Milwaukee first round pick they had acquired in the McCollum deal to Detroit as the centerpiece of a package to acquire forward Jerami Grant. 

As the 2022-2023 season began the Blazers 2018 first round pick, Anfernee Simons, stepped into a full-time starting role alongside Lillard.  The team hovered around .500 for much of the season and was 28-30 when it reached the All-Star break.  At the trade deadline, the organization had essentially waived the white flag on the season, shipping Josh Hart, who had been acquired in the McCollum deal, to New York in exchange for the Knicks 2023 first round pick. 

The Blazers struggled down the stretch despite Dame setting new career highs in points (32.2) and effective field goal percentage (56.4%).  After a late March win in Salt Lake City brought the team’s record to just 32-40, the Blazers shut Dame down for the last 10 games of the season.  The decision created more opportunity for rookie Shaedon Sharpe who the team had drafted with the 7th pick of the 2022 draft but, the team would win just one game the rest of the season to finish at 33-49, the same record as Lillard’s rookie year…

Portland entered the 2023 draft lottery slotted 5th and the ping pong balls bounced their way awarding the organization the #3 pick in the 2023 draft.  The speculation over Dame’s future had grown much loader than the previous offseason and it appeared the organization was headed towards a fork in the road.  Either trade the pick in a deal that would land another star player to pair with Damian Lillard or commit to a rebuild and trade Lillard for assets that could help accelerate that process and provide Dame with an opportunity to contend for a championship. 

As draft night approached without any signs of a trade, Dame’s exit from Portland seemed inevitable.  On the night of June 22, 2023, with the 3rd pick in the NBA draft, the Portland Trail Blazers selected point guard Scoot Henderson of the NBA G League Ignite.  The Trail Blazers now had a crowded backcourt that included three young guards in Henderson, Sharpe, and Simons.  Nine days later, on July 1, 2023, reports surfaced that Lillard has requested a trade and Blazers General Manager, Joe Cronin, released a statement confirming that Dame would prefer to play elsewhere. 

Dame’s time with the Portland Trail Blazers is rife with what ifs...What if Matthews hadn’t torn his Achilles tendon in March of 2015?  What if Aldridge hadn’t left in July of 2015?  What if the team hadn’t made the Nurkić trade and allowed a down season to playout in February of 2017?  Would they have been in position to draft Lauri Markkanen or even Jayson Tatum?  What if the Trail Blazers had just drafted Bam Adebayo instead of Zach Collins in 2017?  What if Portland had packaged their 2017 draft picks and future picks with Meyers Leonard? Could they have acquired Jimmy Butler who was traded from Chicago to Minnesota that summer?  What if they had waited until the summer of 2022 to shop McCollum instead of dealing him during the season?  Could they have found a better deal?  What if there was an opportunity to land another All-Star by trading the #3 pick in the 2023 draft?...

The reality is that constructing an NBA championship roster is incredibly difficult.  Organizations often face roster decisions that do not have definitive right answers.  Even when they do end up on the right side of those decisions, like selecting a 6’2” guard out of Weber State with the 6th overall pick in the NBA Draft, a team’s results are always impacted by elements outside of an organization’s control. 

What is within the Trail Blazer’s control, is what happens next with Damian Lillard, who has four years remaining on his contract.  Dame has done everything that could have been asked of him to try to deliver a title to Portland and unfortunately has never had enough help around him to do so.  With the organization clearly headed towards a rebuild, they owe it to Lillard to send him to a team in position to contend for an NBA title.  

Perhaps the best comparison for Lillard’s circumstances is the crossroads Kevin Garnett found himself at in the summer of 2007.  Garnett had dedicated the past 12 years trying to bring a championship to Minneapolis.  Like Lillard, he had only managed to reach the Western Conference Finals once, a six game defeat at the hands of the Lakers.  He was also two years into a new coaching staff on a team whose record was headed in the wrong direction. 

KG and the Minnesota front office worked together to find him an opportunity to compete for a title and he landed with the Boston Celtics that summer.  Garnett would go on to win two Eastern Conference Titles and one NBA Championship (2008).  Garnett was 31 at the time of his trade to Boston and Lillard will turn 33 prior to the start of the 2023-2024 NBA season.  In his Hall of Fame acceptance speech, The Big Ticket stated that his only regret was that he hadn’t come to Boston earlier in his career. 

For some fans of the NBA, what can be easily lost in all the money and the fame that comes with superstar status, is how much players truly love the game of basketball and how hard they have worked for the opportunity to compete at the highest level.  The NBA is by far the most competitive basketball league in the world but, there’s a big difference between the regular season, the first couple rounds of the playoffs, the conference finals, and ultimately the NBA Finals.  As Meek Mill once said, there’s levels to this shit!

Dame came close to in 2019 but, the sand in the hourglass of his career is quickly running out.  Lillard has dedicated much of his life to the game of basketball and the Trail Blazers need to send him to a contender now…

It's Dame’s time!