The Milwaukee Bucks are coming off another rough first-round playoff exit, something that has been a recurring theme since the franchise won the championship in 2021.
Since winning the title in 2021, Milwaukee has advanced out of the first round of the playoffs just once, which came in 2022 when they were eliminated in the second round.
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Milwaukee will now enter the 2025-26 season looking to turn things around and make a run at a title behind their superstar forward Giannis Antetokounmpo.
Milwaukee Bucks forward Giannis Antetokounmpo (34) shoots the ball while Indiana Pacers center Myles Turner (33)© Trevor Ruszkowski-Imagn Images
Of course, the Bucks also added Myles Turner and Cole Anthonyt in free agency this offseason and also re-signed Bobby Portis, Gary Trent Jr. and Kevin Porter Jr.
Despite this, the Bucks allowed Brook Lopez to leave in free agency and they also waived Damian Lillard in order to sign Turner.
With these moves, Milwaukee will try to make a deep playoff run this season, though they may need to add more talent to their roster ahead of the trade deadline.
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Bucks Could Target Jrue Holiday
One player the Bucks could target ahead of the deadline is a player who was apart of their title team in 2021, Jrue Holiday.
Boston Celtics guard Jrue Holiday (4)© Gregory Fisher-USA TODAY Sports
Milwaukee is in need of point guard depth after waiving Lillard and while Anthony and Porter Jr. are solid guards, adding Holiday to be their starter could work out well.
Mock Trade Sends Jrue Holiday to Bucks, Kyle Kuzma to Blazers
In a potential trade, the Bucks could send Kyle Kuzma and Ryan Rollins to the Portland Trail Blazers in exchange for Holiday and draft capital.
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For the Bucks, moving Kuzma would be a tough decision after they traded away Khris Middleton for him last season, though he did struggle at the end of last year.
Milwaukee Bucks forward Kyle Kuzma.© Benny Sieu-Imagn Images
Because of this, Milwaukee may be open to moving Kuzma, especially to reunite with Holiday who played a key role during their championship run in 2021.
For Holiday, he would give the Bucks a much-needed starting point guard who is a great scorer, playmaker and defender and also already has chemistry with Giannis.
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Last season, the 35-year-old guard averaged 11.1 points, 43 rebounds, 3.9 assists and 1.1 steals per game while shooting 44.3% from the field and 35.3% from three.
Boston Celtics guard Jrue Holiday (4)Bob DeChiara-Imagn Images
While Holiday’s has declined some over the past two seasons, mainly due to him not being a main option for the Boston Celtics, that could change with a return to Milwaukee where he would likely have a large role alongside Giannis and Turner.
Despite this, the Trail Blazers may not want to swap Holiday for Kuzma, which would likely result in Milwaukee looking elsewhere to add another point guard.
This story was originally reported by Athlon Sports on Sep 23, 2025, where it first appeared in the NBA section. Add Athlon Sports as a Preferred Source by clicking here.