When news broke on Wednesday afternoon that Damian Lillard had been traded to the Milwaukee Bucks, the overall reaction around the league was shock. There had been nothing linking the Bucks to a serious pursuit of Lillard, as the only rumblings about any talks happening had been linking the Raptors and, to a lesser degree, the Bulls to conversations about Dame — while Miami remained the preferred destination, but not one Portland would really engage with.
Ultimately, the three-team deal that emerged saw the Blazers choose a deal that brought Deandre Ayton, Jrue Holiday, a future first, and a pair of pick swaps to Portland. Holiday is expected to be moved again to a contender, although the timetable on him ending up with a new team is still to be determined as it’s possible the Blazers could wait until closer to the trade deadline to see if any contenders become desperate for a high-level point guard. In any case, the trade represented a seismic shift leaguewide, but particularly in the East where the Bucks cemented their place as favorites and the Heat now must head back to the drawing board.
Still, losing Jrue Holiday is not an insignificant departure for the Bucks, as his presence was considerable in helping them win a title in 2021, authoring one of the great individual plays of that Finals with his Game 5 steal in the closing seconds, with a lob to Giannis Antetokounmpo on the other end. While many of us were thinking about the terrifying prospect of Lillard playing alongside Giannis and how that will stretch defenses to their limit, Giannis was torn about the trade. While excited to play with someone Lillard’s caliber, he also wanted to keep focus on losing Jrue and what that means on and off the court for Milwaukee in his first comments to Chris Haynes.
“Jrue is my f–king brother for life. I love his family. I love him. I appreciate him. I wish him nothing but the best. He blessed me with a f–king championship,” Antetokounmpo told B/R. “He’s the one who made that huge steal in Game 5 of the Finals. I went to battle with him multiple times. F–k basketball. F–k the media shit. This guy is my brother for life, and it’s always going to be like that. He’s going to thrive wherever he ends up.
“Now at the same time, I’m excited to have Dame. He gives us a chance to win a championship. I’m excited to play with the caliber of player that he is. He can score the ball in his sleep and shoot the lights out.
“It’s a bittersweet day for the city of Milwaukee. You get Dame, who is a great player, but you lose a great guy. Jrue took us to the promised land. I’m 10 years in now. I know it’s a business. At the end of the day, Jrue will alway be be my brother for life. He’s one of the best human beings I’ve been around. But we’ve got to focus on the goal to win the championship. Dame wants this. He’s hungry to win, and he’s going to push us. I’m very happy to have him on our team.”
The reality of trading for a superstar like Lillard is you don’t get to do that without giving up a very important piece of your team to do so. Giannis had made it clear to the Bucks this summer that he wanted them to do what they needed to in order to give them the best shot at winning titles long-term, or else he wouldn’t be considering an extension. Trading Lillard was the resounding response from the Bucks, but it came at the cost of Holiday which, as Giannis notes, is a considerable loss.
Holiday was their backcourt leader as a terrific passer and defender, his off-court impact is hard to quantify as he has long been known as one of the great people in the NBA and is a regular in voting for best teammate in the league from his peers. His leadership and presence on and off the court will be missed, and it’s not a surprise that Giannis would want to make that abundantly clear in his first public comments on the trade.
However, it’s hard to deny that the Bucks got an upgrade in Lillard overall, and particularly addressed their biggest postseason need by getting an elite scoring guard to space the floor and provide much more space for Giannis. The one knock on Holiday was his scoring efficiency in the postseason, which further cramped the spacing for Antetokounmpo and made the Bucks offense easier to slow down in the playoffs. Lillard will change that calculus considerably for defenses, and Lillard is, himself, well regarded as a teammate and locker room presence, even if he’s not exactly where he wanted to be after his trade request.