To say that Damian Lillard's time with the Milwaukee Bucks didn't go as planned would be an understatement. Following two early playoff exits, a brutal Achilles tear, and a surprising buyout, Lillard now reunites with the Blazers on a three-year, $42 million deal.
Lillard suffered the Achilles injury on April 27 in Milwaukee's Game 4 loss to the Indiana Pacers. Because of the severity of the injury, how late it happened in the season, and Portland's rebuilding timeline, Lillard is expected to sit out the entirety of the 2025-26 season.
Due to the questionable Larry Nance Jr. trade, the Blazers still owe the Bulls a lottery-protected first-round pick. After signing Lillard, the odds of Portland returning to the playoffs in 2026-27 have significantly increased. If they end a likely five-year playoff drought at that point, Portland's pick would finally convey to Chicago. The timing of it all couldn't be better.
Blazers' pick more likely to convey to Bulls in weak 2027 draft class
ESPN's Jonathan Givony recently noted that the 2026 draft class is projected to be strong, but 2027 "appears to be an especially weak" class. "This is one of the weakest high school classes I've seen in a long time," one scout told Givony.
That's significant, especially considering how weak the 2024 draft class, where Portland luckily came away with Donovan Clingan, was viewed.
The summer of 2027 is a golden opportunity for the Blazers to free themselves from the Nance deal that haunts them. By finally conveying the pick, they'll also open up more opportunities for a potential blockbuster trade as it will become much easier to attach first-round picks under the Stepien Rule. The Blazers will have a more developed young core, valuable Milwaukee picks/swaps, and a healthy Lillard back in the city where he belongs.
Lillard has previously hinted at a return to Rip City to finish out his career, but with his goal of winning a championship still unfinished, we thought a reunion would come further down the road. Family and loyalty have always been a top priority for Dame, and the fact that he has to now take a gap year seemingly played a role in his decision to return to Portland sooner than expected.
Between the deals from Milwaukee and Portland, Lillard is set to make $70 million, making him the highest-paid player this season. Not bad for an injured 35-year-old who now gets to rehab close to his family.
The Blazers can afford to be patient with bringing him back. In fact, they'd be wise to do so, given the weak draft class in 2027.