To Trade or Not to Trade Damian Lillard

Omar Vega
8 min readMar 20, 2023

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I can almost recite the tantrum my lifelong Trail Blazers fanatic of a best friend threw in 2020 after my Los Angeles Lakers beat his team 4–1 in the NBA Playoffs: “We never give Dame (referring to generational talent Damian Lillard) an actual roster to compete with. It’s the same story every single year.” In 2021, Lillard’s Blazers ran into the Denver Nuggets in the first round, losing the series 4–2 as my friend shut off the TNT broadcast in disappointment before the fourth quarter was over. In 2022, they failed to even qualify for the playoffs.

Anyone remotely involved in the chaos of the NBA understands that fans of the Portland Trail Blazers have felt real, tangible pain over the last four seasons. Similar to the seemingly perpetual rain that looms over Portland during these months, a metaphorical cloud has left Blazers fans feeling gloomy since future Hall-of-Famer Damian Lillard hit a game-winning buzzer-beater over the Oklahoma City Thunder in the 2019 NBA Playoffs. That year, they advanced to the Western Conference Finals for the first time since 2000, unfortunately running into the juggernaut that was the Golden State Warriors. Four years ago, Blazers basketball seemed to have peaked, as the hometown team has since made the playoffs only twice, losing in the first round both times, as mentioned. They currently reside in 13th place in the Western Conference. This dark cloud hails the question of where this leaves their star guard and whether he should or should not be traded.

Few players in the professional basketball world are as beloved and respected as Damian Lillard. The Portland Trail Blazers superstar talent has been a force in the NBA since he was selected sixth overall in 2012 and has since established himself as a clutch time enigma of the last decade, becoming one of the greatest point guards in NBA history in the process. Last year, Lillard was named to the NBA’s 75th-Anniversary Team, which honors the top 75 players in NBA history. Despite his brilliance and leadership, many Trail Blazers fans, much to their dismay, feel their superstar deserves to be traded away from Rip City and ride off into the sunset in search of a championship with a contender. The longstanding question of whether or not Lillard should be traded holds leaguewide gravity, impacting not only the Trail Blazers organization but the entire NBA community should a blockbuster trade ever go down.

In 2022, the Trail Blazers traded way Damian Lillard’s running mate C.J. McCollum as part of a seven-player deal. McCollum played with Lillard for nearly nine years. As appreciated as he was for everything he brought as a Blazer, Portland understood their small-guard backcourt could only go so far in the Playoffs and ultimately pulled the trigger. A new approach was necessary.

Portland opened this season with promise, acquiring forward Jerami Grant, a versatile defender who provides consistent scoring on a nightly basis as a second or decorated third option, along with the continued emergence of young combo guard Anfernee Simons. Much of Simons’ improvement involves Lillard’s veteran presence and leadership, lauded by Blazers and NBA fans alike. However, this NBA season has been a rollercoaster, an understatement on many counts. Superstars Kyrie Irving and Kevin Durant were traded to the Dallas Mavericks and Phoenix Suns, respectively, bolstering an already incredibly stacked Western Conference. Russell Westbrook was traded from the Los Angeles Lakers, subsequently propelling LA upwards in the standings. These moves have left the Trail Blazers in the mud, with a record below .500 in the winning column and no legitimate chance at a championship. This has reasonably led to an uproar of fans urging Trail Blazers General Manager Joe Cronin to rebuild, and how trading Lillard may reel in valuable assets and draft picks to help them down the line.

NBA legend Shaquille O’Neal shares the same sentiment, stating the Portland Trail Blazers should do Damian Lillard a favor by pulling a ‘Kevin Durant’: “The organization should do him a solid and trade him to a contender,” Shaq said, per The Big Podcast. “They should use him to get younger pieces because they’re never going to win there if you don’t get him any help.” Like every other superstar in today’s league, Lillard cannot win a championship by himself, never mind at 32 years old.

For an aging player with subtly accumulating injuries, no significant help, and additional reasons, as mentioned above, it is understood why fans believe that their star guard should be traded away. With the appeal of a treasure chest of draft picks, the dream of another Portland contender built from the ground up is reborn yet again. This reality certainly does not involve a happy ending for Trail Blazers fans, but it does deliver on one promise: Giving Dame a shot to win. The truth of the situation is no Cinderella story, however, as trading Lillard would be a monumental mishap — perhaps on par with the franchise passing up on Michael Jordan and Kevin Durant in the NBA Draft — and there are a number of reasons why.

Photo by Sam Forencich/NBAE via Getty Images

Moving Damian Lillard is a potential blunder, both practically and financially, for all sides involved. During the 2022 offseason, Lillard agreed to a two-year maximum contract extension with Portland through the 2026–27 season. According to multiple reports, the deal is worth $225 million. Per Anne M. Peterson of the Associated Press, “Lillard will make about $59 million in 2025–26, then about $63 million the next year. He’ll make about $137 million over the next three seasons before the extension begins.” Again, as a 32-year-old, should a franchise take on such a monster of a contract and compromise valuable assets and draft picks to land a big-name guard? As a diehard Los Angeles Lakers fan, I still have nightmares about the 2021 Russell Westbrook trade. By trading core role players of a 2020 championship team and a 22nd overall pick, the Lakers handicapped themselves for nearly two seasons before saving themselves during last month’s trade deadline by effectively ending the Westbrook era. Russell Westbrook is undeniably a Hall-of-Fame talent, but it has been a bumpy road since his trade from Oklahoma City. Damian Lillard himself had something to say about it: “But then you look at Russell Westbrook. You leave OKC for Houston, then James [Harden] decided he’s leaving, now Russ is traded to D.C., then you get traded from D.C. to the Lakers, now you’re on your fourth team in four years, and in your second year on the team, everybody is talking about how they should trade you. Now you’re coming off the bench. This dude is a Hall of Famer, an MVP. It’s an example that the grass isn’t always greener.”

These comments were made even before Westbrook signed with the Los Angeles Clippers. The Brooklyn Nets traded superstar James Harden for Ben Simmons, a former young prospect with upside who, in retrospect, has been a disaster for the franchise. The grass is certainly not always greener, and Lillard’s feelings on this subject are essential to consider in the context of his contributions to the Team and the city of Portland.

Damian Lillard is more than just a basketball player; he is an icon on and off the court, committed to his Portland and Oakland communities via his RESPECT program. Trading Dame away would not only serve as a blow to the organization for years to come, but to the state of Oregon and its basketball fans. In addition to being amongst the league’s premier fourth-quarter performers, warranting the nickname of ‘Dame Time,’ Lillard’s mantra is primarily focused on his loyalty to the city of Portland. Countless articles recount Damian Lillard’s tweets, post-game interviews, and lyrics about loyalty and keeping the very notion of loyalty in today’s league alive. Eight months ago, he told Chris Mannix of Sports Illustrated how it is “something that’s missing in our league, the passion, the pride, not just for the name on the back but the name on the front.” Moreover, in a March 15th appearance on former NBA sharpshooter JJ Redick’s Old Man and the Three podcast, Damian Lillard shared why he laments the current ‘ring culture’ of the NBA: “While I understand we play to win championships, we can’t keep acting like nothing matters, like the rest of the stuff, the journey doesn’t matter,” he explains. “We can’t keep doing that.” In the current diaspora of NBA contenders comprised of superteams, such an attitude may not resonate with most fans, but Lillard’s deep appreciation for the game itself separates him from a sea of other modern superstars. Such dedication is not something to be disregarded in the case of a blatant trade, especially when the point guard has never outwardly requested one. Damian Lillard’s absence would have a ripple effect on an organization that would struggle to attract any lucrative free agents should they ignore the sentiments of their star.

Furthermore, it is crucial to acknowledge the sheer excellence of Lillard’s career as a lifelong Trail Blazer. A future first-ballot Hall-of-Famer, Damian Lillard boasts seven NBA All-Star selections and six All-NBA Team nods, the only player in Trail Blazers franchise history to do so. He also just won the 2023 NBA 3-Point contest, in addition to being the only player in NBA history, along with Michael Jordan, to cash two buzzer-beaters to clinch a playoff series.

Blazers fans’ desires to rush for a rebuild and acquire valuable assets are understandable, as this is how some mediocre-to-okay teams of the past have completely flipped the script to become perennial contenders (see Milwaukee Bucks, Philadelphia 76ers, and Golden State Warriors). Regardless, trading away a transcendent talent is not the only way to do so. With other forms of acquiring assets, such as through free agency and blockbuster trades or developing their young talent to build a competitor around Lillard, starting from scratch and disrespecting Dame’s tireless efforts to win would be a travesty.

Ultimately, the ball is in the Portland Trail Blazers’ court. Taking a page from the Dallas Mavericks' book, which surrounded then-33-year-old Dirk Nowitzki with elite shooters and defenders to become 2011 NBA Champions, is a great place to begin. Dirk won it all in his 13th season with the Mavericks. Rewarding an aging superstar with a legitimate shot at winning a championship is viable, but it all circles back to front-office competence and if they are as dedicated to winning as Damian Lillard is.

References

Buhler, John. “Was Damian Lillard’s Comment a Shot at Kevin Durant, Other NBA Stars?” FanSided, 10 Jul. 2022, fansided.com/2022/07/10/damian-lillard-loyalty-comment-kevin-durant-nba-stars/.‌

House of Highlights. “Damian Lillard DESTROYS the Thunder with EPIC GAME-WINNER.” YouTube, 23 Apr. 2019, https://youtu.be/a-M3x-eZpV8.

Mistretta, Joey. “‘Grass Isn’t Always Greener’: Damian Lillard’s Russell Westbrook Take Helps Explain Loyalty to Blazers.” ClutchPoints, 27 Feb. 2023, clutchpoints.com/blazers-news-damian-lillard-uses-russell-westbrook-to-explain-portland-loyalty.

Peterson, Anne M. “Damian Lillard Inks 2-Year Max Extension with Trail Blazers.” NBA.com, 10 Jul. 2022, www.nba.com/news/damian-lillard-extension-trail-blazers.

Quinn, Sam. “Damian Lillard opens up on current state of basketball discourse: ‘I don’t enjoy what the NBA is becoming.’” CBSSports, 15 Mar. 2023, cbssports.com/nba/news/damian-lillard-opens-up-on-current-state-of-basketball-discourse-i-dont-enjoy-what-the-nba-is-becoming.

Villanueva, Virgil. “Shaquille O’Neal Says the Portland Trail Blazers Should Do Damian Lillard a Favor by Pulling a ‘Kevin Durant.’” Basketball Network — Your Daily Dose of Basketball, Basketball Network, 3 Mar. 2023, www.basketballnetwork.net/latest-news/shaquille-oneal-says-blazers-should-trade-damian-lillard-to-a-contender.

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