Winners and losers of the Damian Lillard trade

Portland traded franchise player Damian Lillard to Milwaukee, ending months of speculation. Here are the winners and losers of the three-team deal.

Winners

Milwaukee Bucks: The Bucks took a big swing to placate star Giannis Antetokounmpo and push their chips in on a title pursuit. Lillard and Antetokounmpo could form the most potent inside-outside scoring combination since Shaq and Kobe, and the Bucks have the defensive talent to cover for Lillard's occasional lapses on that end. They paid a stiff price in Jrue Holiday and three draft picks, but ultimately a generational talent like Antetokounmpo has to be their immediate focus, rather than a 2030 first-round pick who is probably in seventh grade right now.

Phoenix Suns: They gave up Deandre Ayton, the No. 1 pick from the 2018 draft, but they clearly weren't infatuated with his game. That was clear when they declined to offer Ayton a maximum extension after he helped them to the Finals in 2021, and only signed him after matching Indiana's offer. Now they've exchanged an unhappy center for four additional players, all of whom are cheaper and theoretically more tradeable, but giving their top-heavy roster some much-needed depth and youth.

Portland Trail Blazers: Yes, we're calling this a win for all three teams involved. Blazers general manager Joe Cronin stayed patient and waited nearly three months to trade his superstar point guard. For his patience, he picked up a 25-year-old center in Ayton, and the soon-to-be-traded Holiday, who should get the Blazers more assets for their young core. Best of all, he got picks from after Lillard's contract expires, which means that Portland fans can keep rooting for Lillard without worrying that Milwaukee's success will hurt their draft picks.

It was always in Portland's best interest to ditch Lillard and his huge contract, but this is a respectable return for a team that's been ready for a rebuild for at least a year.

Toronto Raptors: While the Raptors considered a front-runner for Lillard earlier this week, trading for Lillard never quite made sense for them. While he's a great offensive player, adding Lillard to the 41-41 Raptors might not make them a guaranteed playoff team, considering they would have to have given up OG Anunoby and/or Gary Trent Jr. in the deal. Lillard is an upgrade on the departed Fred VanVleet, but not so much that he'd individually transform the Raptors into a contender.

Losers

Miami Heat: The Heat seemingly based their offseason strategy on bringing Lillard's talents to South Beach. They let two starters from last season's Finals team, Gabe Vincent and Max Strus, leave in free agency. Miami also risked alienating guard Tyler Herro, who spent his whole summer hearing himself in trade rumors. Now they're trying to repeat as Eastern Conference champions with Josh Richardson as their biggest offseason pickup. Pat Riley and the Heat have a well-earned reputation of getting stars to come to Miami, but they couldn't pull it off this time.

Star player leverage: The NBA saw trade requests from Lillard and James Harden this summer, both of whom had preferred destinations (Miami for Lillard, the Los Angeles Clippers for Harden). Neither player got what they wanted. It's become standard practice in the NBA for star players to sign big contracts and then direct their way to other cities — Harden did it twice since 2021 — but this time, teams held firm. Lillard demanded a trade just a year after signing a two-year extension through 2026-27. It shouldn't be a surprise that he didn't also get to choose his new team a year later.

Boston Celtics: The Celtics have had playoff success against Milwaukee recently, but now they have to deal with Lillard as well. They'll have to do that without the 2022 Defensive Player of the Year, point guard Marcus Smart, whom they traded to Memphis. In 12 career matchups, Smart has held Lillard to 41.7 percent shooting and only 33 percent from deep. The Celtics might miss that defense if they face Milwaukee in May again.

The deal also makes it much more likely that Antetokounmpo signs an extension in Milwaukee, keeping the Eastern Conference's best player as a roadblock to Boston's title hopes for the foreseeable future.  

Pascal Siakam: Siakam is eligible for a supermax contract if he makes one of the All-NBA teams this year. That's a tough thing to achieve on a mediocre team. The Raptors forward would have had more wins and attention with Lillard on board. Now he's more likely to get traded at the deadline than qualify for a supermax.