Jimmy Haslam is suddenly at the center of two franchise-shaking trades, and the latest one might haunt Milwaukee if the math doesn’t work.

The Giannis Antetokounmpo trade already sent a shockwave through the NBA, with the Milwaukee Bucks reportedly shipping their franchise icon to the Miami Heat instead of taking a Boston Celtics package headlined by Jaylen Brown. But the bigger story might be the owner fingerprints all over it.

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According to Kevin O’Connor, Haslam was a “driving force” in the Bucks choosing Miami’s offer over Boston’s. The logic? Haslam reportedly didn’t want to take on the risk of Brown eventually wanting out of Milwaukee after already dealing with trade demands from Giannis and Cleveland Browns superstar Myles Garrett.

That’s where this gets fascinating — and dangerous.

On paper, there’s a case for wanting “certainty.” Draft picks don’t complain about touches. They don’t leak frustration. They don’t ask out after one uncomfortable season. The Heat package gives Milwaukee a fresh reset built around Tyler Herro, Kel’el Ware, Jaime Jaquez Jr., Kasparas Jakucionis and future draft capital. That’s a lot of optionality for a franchise that just moved the best player in its history.

But let’s not pretend this is risk-free.

Jaylen Brown is an established NBA star. He’s a proven playoff scorer, a two-way wing and the kind of player most rebuilding teams would crawl through broken glass to land. Passing on him because he might eventually want out is one of those decisions that can look smart in a boardroom and brutal on the court.

Haslam’s logic also carries some Cleveland baggage. The Browns have spent years trying to escape dysfunction, and the Myles Garrett trade to the Rams was another massive reset under his watch. Now, less than a month later, Haslam’s Bucks involvement is tied to the decision that ended the Giannis era in Milwaukee.

That’s a lot of chaos for one owner’s summer.

To be fair, Giannis’ exit was probably coming. Once a superstar of his caliber starts looking around, the clock gets loud fast. The Bucks had to act, and Miami’s offer gave them multiple young players and picks instead of one expensive star with his own future leverage.

Still, this is the kind of move that defines an ownership group.

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If Herro scores, Ware develops, Jaquez pops and the picks turn into real building blocks, Haslam will look disciplined. If Brown keeps playing like a star and Milwaukee spends years searching for its next centerpiece, this will look like the Bucks overthought their way out of a cleaner answer.

Either way, the Giannis trade isn’t just the end of an era.

It’s Jimmy Haslam’s Milwaukee test.