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Why the Damian Lillard trade request seemed inevitable despite previous patience to Blazers

For his entire NBA career, Damian Lillard expressed devotion, patience and loyalty to the Portland Trail Blazers. He conveyed that dedication as he blossomed into one of the NBA’s best scorers and led the Blazers toward becoming one of the league’s most consistent teams. He maintained that perspective even through early playoff exits, when other stars forged super teams and amid overlapping personal and team-wide injuries.

Eventually, Lillard changed his sentiments. He requested for the Blazers to trade him, as The Athletic, Bleacher Report and ESPN all reported on Saturday morning. The Blazers technically don’t have to oblige considering Lillard is in the second-to-last year of his four-year, $176 million contract before his two-year extension becomes effective on 2025. But in today’s NBA, most teams eventually accommodate those requests in hopes to sell high.

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Lillard may have taken an abrupt turn from his previous sentiments, but it shouldn’t surprise anyone that it played out this way.

Entering his 12th NBA season, Lillard wanted Portland to field a championship-caliber roster around him. Instead of dealing the No. 3 pick for an established veteran, however, the Blazers drafted a dynamic point guard (Scoot Henderson) that may need time to develop. Lillard and his agent, Aaron Goodwin, met with Blazers general manager Joe Cronin earlier this week to talk about the state of the franchise.

After Cronin pledged in a statement that “we remain committed to building a winner around Dame,” the Blazers then spent the first day of free agency showing their limitations. Portland secured forward Jerami Grant to a five-year, $160 million deal, which signified two things. Perhaps to assuage Lillard, the Blazers showed commitment toward retaining a key veteran whom Lillard recruited and instantly formed strong chemistry. It also suggested that would be the best transaction the Blazers could make.

By that point, it only seemed to be a matter of when and not if Lillard would request a trade. Maybe he would wait until the Blazers finalized all of their off-season roster moves. Maybe he would wait to witness any early-season hiccups. Maybe he would wait until next season’s trade deadline. No need to wait, though. The Blazers don’t appear close to becoming a title contender. So why delay the inevitable?

In fairness, the Blazers didn’t do anything necessarily wrong. NBA talent evaluators love Henderson’s playmaking and leadership. The Blazers couldn’t find a worthy veteran player to trade for with its No. 3 pick. Had they somehow landed Pelicans forward Zion Williamson, the Blazers would still remain vulnerable with Williamson’s durability concerns. And the Blazers have a nice young nucleus with Anfernee Simons and Shaedon Sharpe. All of that might make the Blazers a competitive playoff team just like when they appeared in eight consecutive post-season appearances with Lillard. But they wouldn’t come close toward becoming a title contender.

After experiencing injuries in the past two seasons, the 32-year-old Lillard understandably wants to ensure his championship window doesn’t completely shut. So why waste any more time playing in yet another season in which the Blazers could become good, but not quite good enough? Why waste any more time adding mileage to an engine that eventually will feel Father Time’s strain without a serious chance at winning a title?

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It might have felt painful for the Blazers to have heard Lillard’s trade request. In a way, though, the Blazers should thank Lillard for making a difficult decision somewhat easier. Why wait to deal Lillard when they could arguably receive the best offer as other teams hope to make dramatic off-season moves? Why wait to trade Lillard when his value could diminish with additional wear-and-tear? Why wait to hit the reset button when they can grow their young players organically without the understandable pressure Lillard will feel to contend immediately? That partly explains why Blazers’ first day of free agency seemed puzzling. It’s understandable to retain Grant either to appease Lillard or to attach him as part of the future Lillard trade. That five-year contract could become too much for another team to take.

It’s sad that this partnership will end soon. Lillard had resisted any urge toward leaving for a bigger market or forming a super team amid appreciation for what he and the Blazers accomplished together. The Blazers appeared in the postseason for eight years, including a trip to the 2019 Western Conference Finals. Lillard became the Blazers’ all-time leading scorer (19,376 points) and 3-point shooter (2,387 makes), while faring second in assists (5,151). And even if the Blazers never could make the big free-agency splashes, they still remained competitive with fielding another strong backcourt player (CJ McCollum) while acquiring quality role players that often performed above their potential.

That explains why Lillard didn’t deserve criticism for not wanting to leave earlier. He appreciated the value of building something organically. He appreciated the organization’s collaboration. And both parties didn’t shy away from have difficult conversations. But Lillard also doesn’t deserve any heat for finally wanting to end this partnership. It became clear that the Blazers hit their ceiling.

Despite making eight consecutive playoff appearances and winning two Pacific Division titles, the Blazers often amounted toward nothing more than becoming dangerous playoff team. The Warriors swept them in the 2019 Western Conference Finals despite missing Kevin Durant for the entire series with a strained right calf. The Blazers lost to the Denver Nuggets in the first round of the 2021 NBA playoffs despite point guard Jamal Murray missing the series with an ACL injury.

The Blazers eventually replaced Terry Stotts with Chauncey Billups as head coach two seasons ago, but that hasn’t yielded dramatic changes just yet. Cronin replaced Neil Olshey at general manager later in 2011-22 following reports of how he contributed to a toxic work environment. From a basketball standpoint, though, Cronin currently has just upgraded the team on the margins. He eventually made the tough decision to deal McCollum leading into the 2022 trade deadline, but the Blazers field a young roster that still needs more time to develop. It also didn’t help that Lillard has experienced serious injuries in recent seasons. After playing in only 29 games in the 2021-22 season before and after having surgery to treat a lingering abdominal injury,  Lillard appeared in only 58 games last season because of a right calf injury.

Neither the Blazers nor the Lillard believed or hoped it would lead to this point. They stayed optimistic they could stay in the trenches, thrive through the grind and benefit from sustained loyalty. After trying to find solutions, though, both parties soon ran into the same challenge. The Blazers couldn’t field a title-contending roster around Lillard. That would leave the burden on Lillard to perform almost all of the heavy lifting.  

Therefore, Lillard took that painful albeit necessary step toward initiating a divorce. Never does such a decision yield a happy ending. But perhaps because of the equity they built with each other, both parties can take solace that they explored all solutions before Lillard reached a breaking point. Perhaps that makes Portland amenable toward following through on Lillard’s request amid hopes they at least can receive help for taking their next steps.

Mark Medina is an NBA insider for Sportsnaut. Follow him on Twitter and on Instagram.

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