You simply had to be there to believe it. The Milwaukee Bucks weren’t supposed to land Damian Lillard last summer until they did. For months prior to that move, Miami was widely expected to be his next destination. It was almost an inevitability at that point, except when trade talks stalled, the Bucks seized their moment, swooping in to form a lethal duo of Lillard and Giannis Antetokounmpo.
Now, history might be setting up for a repeat.
With the NBA Trade Deadline approaching, rumors of Jimmy Butler’s potential availability are growing. Miami’s slow start, along with Butler’s looming contract extension demands, has raised questions about his long-term future with the Heat. He's available, and the Bucks could once again play spoiler, stealing another superstar from Pat Riley’s grasp—just like they did with Damian Lillard.
The question now is this: Could the same formula work for Jimmy Butler?
NBA insider Marc Stein’s latest report on The Stein Line (subscription required) reinforces that the Bucks are a team to watch as the trade deadline approaches. While Milwaukee can’t currently package contracts for Jimmy Butler unless they first move Pat Connaughton, a deal involving Khris Middleton and Bobby Portis could be a viable framework if they clear that hurdle.
Such a move would provide Miami with two playoff-proven veterans on manageable contracts—potentially a better outcome than playing without Butler entirely.
If the Bucks are eyeing another superstar, history says it's possible
The Lillard trade was a masterclass in patience, perseverance and business acumen on the part of Milwaukee general manager Jon Horst.
To recall, the Heat spent months upon months haggling over assets, believing they were the only viable suitor. Meanwhile, the Milwaukee Bucks stayed quiet, waiting for the right moment to strike. When Portland refused to send Lillard to Miami, Milwaukee jumped in, packaging Jrue Holiday, draft capital and role players to secure the deal.
Butler doesn’t have a no-trade clause, meaning Miami doesn’t have to send him to his preferred destination. If the Heat decide to move on from their 35-year-old star, the highest bidder will win. And given the Bucks’ track record of going all-in, it’s not impossible to imagine them making a play.
Regardless of whether a Butler pursuit materializes, Marc Stein's report makes one thing clear: the Bucks are among the most aggressive teams in the league in their pursuit of a trade. They are determined to make at least one move to bolster the roster around Giannis Antetokounmpo and Damian Lillard, aiming to strengthen their title chances before the deadline buzzer sounds.
At full strength, the Bucks are already one of the best teams in the East, at least on paper. But injuries, defensive inconsistency and a lack of wing depth have raised questions about whether this roster is truly built for a deep playoff run. For the most part, their scoring is still extremely dependent on their superstar duo, while younger teams can very easily run them off the floor on any given night. Adding Jimmy Butler would immediately address those concerns.
Butler remains an elite two-way force. He could take on top defensive assignments, relieving pressure on Giannis and Brook Lopez. Unlike Zach LaVine or Bradley Beal, Butler has proven he can elevate his game in the postseason.
In Miami, he’s dragged lesser rosters to the Finals twice. A duo of Butler and Giannis could create one of the most physically imposing pairings in recent memory. It would signal the end of an era for sure, but it could also be the missing piece for playoff glory.
One major roadblock in the trade market right now is Bradley Beal’s no-trade clause. If the Phoenix Suns wanted to move him (as some reports suggest), he’d have full control over where he lands. Beal has been linked to Miami in the past, but his ability to veto a deal could keep that from happening.
Bradley Beal is still the wild card in Milwaukee's best-laid plans right now
If the Heat’s alleged Plan A in Beal stalls out or falls apart altogether, then Butler’s status becomes even more interesting. Would Miami pivot toward reshaping its roster? If so, the Milwaukee Bucks would be wise to keep a close watch.
The biggest obstacle in a potential Bucks-Butler trade is asset flexibility. Milwaukee doesn’t have a war chest of picks, and their best trade pieces—Khris Middleton, Bobby Portis and Pat Connaughton—aren’t as enticing as younger assets other teams might offer.
However, if the market for Butler is lukewarm due to his age, contract demands, or Miami’s unwillingness to send him where he wants to go, the Milwaukee Bucks could pounce. Just like with Lillard, it might take a perfect storm of factors falling into place.
The odds of Milwaukee actually landing Butler remain slim, but so were the odds of them landing Lillard in 2023. If Miami drags its feet in negotiations or Butler suddenly becomes available, the Bucks have shown they’re willing to act fast.
History has a funny way of repeating itself. If Milwaukee gets another opportunity to steal a superstar from Miami, don’t be surprised if they do it again.
Stay tuned for more Milwaukee Bucks analysis.