The Milwaukee Bucks are at a crossroads. For nearly a decade, they’ve remained a postseason staple. That’s largely thanks to the brilliance of Giannis Antetokounmpo. However, the team’s 2025 offseason has arrived with less optimism than ever. For the third straight year, the Bucks failed to advance past the first round of the NBA Playoffs. This time, they fell to the Indiana Pacers after a 48-34 regular season. While they deserve credit for reaching the playoffs for the ninth consecutive year, the truth is painfully clear. This version of the Bucks isn’t good enough to win another title.
This is not just a media hot take. It’s a growing belief within NBA front offices.
“The cycle closes when your core players get older and there is no foundation of young players waiting to replace them,” an Eastern Conference GM told ESPN. And with Lillard turning 35, Brook Lopez nearing retirement, and Bobby Portis potentially walking in free agency, Milwaukee’s foundation is crumbling.
Still, not all is bleak. Antetokounmpo is under contract through 2028. In addition, the Bucks aren’t trapped financially the way they were in previous seasons. The Khris Middleton-Kyle Kuzma trade has added flexibility. Also, the team can shop for trades that bring much-needed shooting, defensive intensity, and youth. Milwaukee has a narrow windoe to reshape its roster through savvy moves.
Here we will discuss the two players whom the Milwaukee Bucks must target to sign as they enter the 2025 NBA offseason.
Let’s begin with Kentavious Caldwell-Pope. He won’t require a treasure chest of draft picks or prospects. Sure, KCP may not be the splashiest name on the market. However, his pedigree as a proven 3-and-D wing and a two-time NBA champion makes him an ideal fit on a contending team. This is especially true for a team like Milwaukee that desperately needs wing depth and perimeter defense.
Caldwell-Pope had a rough debut season in Orlando. He struggled to find rhythm and finished with just a 34.2 percent three-point shooting mark. That was his lowest since the 2015-16 season. But that may say more about the Magic’s offense than it does about KCP’s decline. The Magic paid a premium—three years, $66 million—for a player who hasn’t yet lived up to expectations in their system.
Enter the Bucks.
In Milwaukee, Caldwell-Pope would benefit from the gravity of Antetokounmpo and Lillard. They would attract swarming defenses and open up looks for shooters. Late last season, the Bucks were at their best when they spaced the floor around Giannis. They ran out lineups that featured shooters like Kevin Porter Jr, Gary Trent Jr, and AJ Green. With that context, it’s not hard to imagine KCP rediscovering his shooting stroke in Cream City.
More importantly, the acquisition cost for KCP should be manageable. Orlando would likely entertain offers to clear cap space or acquire younger talent. Milwaukee could build a package around smaller contracts or a second-round pick to get the deal done. For a team seeking cost-effective solutions, KCP might be the perfect fit.
Now let’s talk big swings. Michael Porter Jr fits that mold. The 6’10 forward remains one of the NBA’s most intriguing yet polarizing talents. On one hand, he’s a hyper-efficient scorer capable of lighting up defenses with his silky jumper and off-ball movement. On the other, he’s had durability concerns and carries a hefty contract. Remember that he’s owed over $35 million annually through 2027.
Now, the Bucks need to upgrade their offensive firepower around Antetokounmpo. Porter offers a rare blend of floor-spacing and shot creation that few forwards his size can match. His shooting splits flirt with elite levels. He shot 50.4 percent from the field, 39.5 percent from three, and 76.8 percent from the line in 2024-25. Porter also averaged 18.2 points and 7.0 rebounds while operating as Denver’s third option. Milwaukee could offer him a larger role and potentially unlock a new level in his game.
Defensively, Porter still has room to grow. That said, he’s improved over the past two seasons. With Giannis anchoring the defense, the Bucks can absorb some of Porter’s limitations while maximizing his offensive strengths.
To make this trade work, the Bucks might need to part ways with multiple rotation players and future draft capital. However, if they’re serious about remaining in the championship conversation, Porter could be worth the gamble. He’s 26, under contract, and capable of providing a jolt to a team that’s lost offensive identity when Giannis sits or Lillard is hurt.
The Bucks can’t afford to play it safe anymore. The days of leaning on Giannis to paper over roster flaws are dwindling. Additionally, Lillard’s age and health only intensify the urgency. Milwaukee must maximize the next two seasons while Antetokounmpo is still in his prime and under contract.
Whether it’s buying low on a struggling veteran like Caldwell-Pope or betting big on the talent of Michael Porter Jr., the Bucks need to take calculated risks. Incremental change won’t cut it. A first-round ceiling is unacceptable for a franchise that raised a championship banner just four years ago.
The window is still open—but only if Milwaukee acts decisively.
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