When Damian Lillard’s acrimonious split from the Trail Blazers emerged in full public view, no fan embroiled in the drama could have foretold his quick return to Portland. Yet, that’s exactly what happened, despite the long-held belief that Portland isn’t a top-tier free-agent destination—and we have Myles Turner to thank for it.
The origin story of the transaction ultimately has roots in 2024’s offseason, where it was announced that perennial all-star Khris Middleton underwent arthroscopic surgery for both ankles. One of those surgeries was to address an injury sustained during the regular season, but the other one was a minor cleanup procedure. With the recovery time on the optimistic side, the Bucks charged headlong into the 2025 season, expecting Middleton back sooner rather than later.
Despite initial timelines indicating he would be ready to hit the ground running when the season began, Middleton returned on December 6 and struggled to reacclimate, putting up mediocre (some might even say middling) stats for nearly two months.
On February 5, Middleton found himself on the Washington Wizards in a move that GM Jon Horst called “the toughest of [his] career.” The Bucks received Kyle Kuzma in the trade, signaling a possible shift to a (more) youth(ful) movement in Milwaukee.
Bucks' desperation led to Lillard's Blazers reunion
It seems like basketball-adjacent news outlets have been pushing the narrative that Giannis Antetokounmpo is unhappy in Milwaukee on an annual basis. Antetokounmpo, on the other hand, has been steadfast in his loyalty to the franchise that drafted him, and the forthcoming moves on Milwaukee’s docket seemed to echo that, kicking the can down the road to the next offseason.
When Myles Turner indicated a willingness to leave the team with which he had just reached the Finals, the Bucks opted to let Brook Lopez walk, and Milwaukee suddenly found itself in an unfavorable salary situation. Turner was in a situation eerily similar to Milwaukee; Indiana’s star guard Tyrese Haliburton had also gone down with an Achilles injury, leaving Indiana with a one-year gap in Haliburton’s career and a highly diminished path to repeat success. Recognizing this, Turner migrated north.
With Lillard being the last remaining piece of the veteran triumvirate, the front office attempted to trade Lillard to a team, any team, that would be willing to reciprocate with draft compensation or other fluid assets. As Lillard was staring down the barrel of a full year of Achilles rehab, the Bucks simply waived him and opted to stretch his remaining salary.
The Blazers signed Lillard to a sweetheart deal, paying him roughly $14 million per season for the next three. That deal will take Lillard through his age-38 season, though much of his game will translate in the interim. In his season before the injury, Lillard averaged 25 points and seven assists while shooting 37.6% from three—all three stats above his career averages to that point.
Again, Portland has never been seen as a high-profile free-agent destination; Evan Turner had been the team’s highest-profile signing in the last 15 years. But when the iron arrives hot, one has no choice but to strike. And Joe Cronin struck.