After another season of championship expectations resulting in disappointment, it may be time to explore refining some of the core pieces of the Milwaukee Bucks roster. Fresh off of an All-Star and NBA All-Defensive First Team season in 2022-23, Jrue Holiday is undoubtedly the most coveted player on the Bucks roster not named Giannis Antetokounmpo. Here are some players that may be available this summer who the Bucks may need to consider trading Jrue Holiday for.
Damian Lillard, Portland Trail Blazers
In the first round series against the Miami Heat, we saw the Bucks really struggle offensively, which ultimately led to the team blowing two double-digit leads in the fourth quarter. This included two stretches where the Bucks didn’t score for over three minutes. Acquiring Lillard would solve that issue, as he is a threat to score from anywhere in the half-court.
Although he will be 33 at the start of next season, the Blazers guard hasn’t shown any signs of slowing down, averaging a career-best of 32.2 points per game in the 2022-23 season. Lillard may not be remotely close to the defender that Holiday is, but the generational shot-making ability that he possesses would alleviate much of the pressure that rests on Giannis’ shoulders throughout the season.
For the past few offseasons, a frequent question has been whether Lillard and the Blazers will finally part ways. The star point guard will be entering his 12th season, meaning he is in the later stages of his career. Joining a win-now Bucks team would make sense for Lillard, who expressed he would be interested in teaming up with Giannis in a tweet a year ago. Trading for an All-NBA caliber player like Lillard would likely require giving up more than Holiday, meaning valuable pieces such as Bobby Portis or future draft picks would likely be included in a deal.