Jimmy Haslam learned the hard way what happens when you bet on a superstar who doesn’t want to be there. And he wasn’t about to make that same mistake twice.
When the Milwaukee Bucks and Miami Heat agreed to a blockbuster Giannis Antetokounmpo trade on Monday night, there was a version of that deal that sent Jaylen Brown to Milwaukee instead of the package Miami ultimately gave up. According to Yahoo Sports’ Kevin O’Connor, Haslam — who co-owns both the Bucks and the Cleveland Browns with his wife Dee — vetoed the Brown trade because he’s still scarred by the Myles Garrett saga.
Garrett forced his way out of Cleveland this offseason after years of drama and dysfunction. Haslam watched that nightmare play out in slow motion. He didn’t want to relive it in Milwaukee.
Here was the problem with Brown. The 2024 NBA Finals MVP was coming off a championship run in Boston and nobody knew if he actually wanted to be the centerpiece of a rebuild in a small market like Milwaukee. If Brown had arrived and immediately started agitating for another trade, the Bucks would have been stuck trying to flip him under duress. That’s a terrible position to be in. Haslam knows that better than anyone.
The Ghost of Garrett’s Trade Request
The Browns didn’t just lose Garrett. They lost a year-plus of constant media noise, locker room tension and failed attempts to reconcile before eventually shipping him to the Rams for what felt like pennies on the dollar. Milwaukee didn’t want to go through that with Antetokounmpo either. The Bucks had tried to build another contender around Giannis and couldn’t get it done. When he asked out, they needed a clean break. Not another potential headache.
Brown has played in high-stakes games his entire career. He just won a title. Asking him to lead a team that’s clearly entering a transition phase felt risky. Would he buy in? Or would he be looking for the first exit ramp?
Haslam and the ownership group opted for certainty instead. They took Pat Riley’s offer: Tyler Herro (a 2025 All-Star), Jaime Jaquez Jr. (this year’s Sixth Man runner-up), center Kel’el Ware, guard Kasparas Jakucionis, the 13th overall pick in the 2026 draft, two future first-rounders, a pick swap and a second-rounder. That’s a young core with no timetable pressure. They can grow together or be flipped later. No drama necessary.
Fans should probably feel good about the haul. But knowing that Haslam’s past trauma shaped this decision? That might make some people uneasy.
The Browns haven’t been stable under Haslam. The Bucks haven’t been either since their title. And now the owner who couldn’t figure out how to keep Myles Garrett happy made the call on a franchise-altering trade for a team that just lost its own generational superstar. We’ll see how that plays out.
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