The acquisition of Damian Lillard by GM Jon Horst and the Milwaukee Bucks is arguably the biggest gamble of the Giannis Antetokounmpo era and maybe in Bucks franchise history.
Sending out one of the Big Three from the championship core in Jrue Holiday to create one of the best duos in the league seemed to guarantee a deep playoff run.
Yet injuries derailed any chance of that, as the Bucks would lose to the Indiana Pacers in six games, with Lillard missing two. Meanwhile, Jrue Holiday got rerouted to the Boston Celtics and helped them finally get over the hump as they beat the Dallas Mavericks in five games in the NBA Finals. So in the end, was the Damian Lillard trade worth it just based on one year? Let’s review Lillard’s first season in the Brew City and answer that question.
Before we even look back on Lillard’s on-court performance, we must look at the circumstances and context of how Lillard ended up in Milwaukee in the first place—Lillard’s time with the Portland Trail Blazers slowly started to come to an end following their Western Conference Finals appearance in 2019. They got bounced in the first round the next two seasons by the Los Angeles Lakers and Denver Nuggets and then missed the playoffs the two seasons after that with Lillard missing 77 games. Lillard officially requested a trade before this season and he seemed destined to head to the Miami Heat to play with Jimmy Butler and Bam Adebayo.
In a shocking move, the Bucks traded Jrue Holiday, Grayson Allen, an unprotected 2029 first-rounder, and two first-round pick swaps in 2028 and 2030. Later, Holiday would be dealt to the Celtics for Malcolm Brogdon and Robert Williams. It seemed the duo of Giannis and Dame was a match made in heaven, with Lillard’s dynamic shooting ability and gravity along with Giannis’ dominance in the paint. Lillard mentioned early in the season that it would be a tough task for opposing teams to defend a pick-and-roll between the two All-NBA players. Lillard said this to Eric Nehm and The Athletic in October of 2023:
“And he’s just standing there like (acts out Antetokounmpo pointing to the sky), so I just throw it up. And in his head, he’s thinking like, ‘Nobody’s going to get the ball if you throw it up there. I’m going to get it before anybody else gets it. So that was different for me. And I threw it up. He jumped up, caught it, turned and he just two-hand dunked it real quick. And it was like, ‘I’ve never played with nobody that’s capable of that.’ So, it’s just different because it was like, that’s a cheat code. To just be able to throw a ball up and have somebody be coordinated enough to hold his guy off, go up, catch it, come down on balance, go up and no dribble, no step and dunk it, you know, over people. So, I mean, it’s… it’s definitely different, man.”