Should Bucks Pursue Jimmy Butler Trade Amid Recent Developments?

Milwaukee's longtime playoff nemesis seems to be ready for a change of scenery.

Nov 26, 2024; Miami, Florida, USA; Milwaukee Bucks guard Damian Lillard (0) protects the basketball from Miami Heat forward Jimmy Butler (22) during the third quarter at Kaseya Center. Mandatory Credit: Sam Navarro-Imagn Images / Sam Navarro-Imagn Images

The Milwaukee Bucks' longtime playoff nemesis, six-time All-Star Miami Heat small forward Jimmy Butler, seems to be ready for a change of scenery.

Recently reports from Shams Charania of ESPN suggested that Butler would prefer being flipped from the Heat to the Golden State Warriors, his hometown Houston Rockets, the Dallas Mavericks, and potentially the Phoenix Suns — although Butler's own agent, Bernard Lee, disputed Charania's claim about the Suns.

So what would a trade look like?

Let's take a dive into ESPN's NBA Trade Machine and do a little dealing.

Obviously, Khris Middleton makes the most sense to include in any exchangel. He's on a $31.7 million agreement for this year and is under contract through 2025-26, is a former three-time All-Star who surprisingly is two years younger than Butler (although Butler has aged much better on the court) plays the same position and gets hurt almost constantly. Butler would represent a major upgrade over Middleton, and at this point Bucks fans might be open to a fresh start from one of their core 2021 championship pieces. Unfortunately, after that is where things get a bit dicey. One possible deal could see beloved sixth man power forward/center Bobby Portis' $12.6 million contract and washed-up backup shooting guard Pat Connaughton's $9.4 million deal get included in the agreement. Portis and Connaughton were key contributors to the team's 2021 championship squad.

Connaughton has fallen out of favor in Doc Rivers' Milwaukee rotations, with AJ Green rising as a better two-way reserve shooting guard.

In terms of draft equity, the Bucks only have their own pick in 2031, which they cannot move due to the Stepien Rule, and a 2031 second rounder, which they can ditch. They cannot even set up a pick swap. So essentially the second rounder and Portis would be the only big positive assets coming back to Miami, aside from Middleton if he can rehabilitate his value at all and stay healthy. It's probably not going to be enough for Miami to pull the trigger on a deal with a much-loathed East rival.

Other clubs possess more draft assets and more intriguing young players on mid-sized deals, making the Bucks a bit of a long shot to acquire Butler's services. Would a "Core Four" of Butler, eight-time All-NBA power forward Giannis Antetokounmpo, eight-time All-Star point guard Damian Lillard, and former All-Star and two-time All-Defensive Team center Brook Lopez be enough to take on the titans of the East? The team would probably still need to build out its depth with some buyout market signings, but certainly — even without Portis — a Butler addition would at least raise Milwaukee's ceiling.

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