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Brad Stevens' biggest gamble just backfired and he may lose more than Giannis

The Celtics had a real chance to pair two of the best players in the NBA in Giannis Antetokounmpo and Jayson Tatum, but instead, they're left with a likely disgruntled Jaylen Brown and more questions than answers.
Feb 4, 2026; Milwaukee, Wisconsin, USA;  Milwaukee Bucks forward Giannis Antetokounmpo (34) during warmups prior to the game against the New Orleans Pelicans at Fiserv Forum. Mandatory Credit: Jeff Hanisch-Imagn Images
Feb 4, 2026; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) during warmups prior to the game against the New Orleans Pelicans at Fiserv Forum. Mandatory Credit: Jeff Hanisch-Imagn Images | Jeff Hanisch-Imagn Images

We’ll surely get more details and clarity on the Celtics’ failed pursuit of Giannis Antetokounmpo in the coming days, and it will be fascinating to see how the team pivots and goes about its business this offseason, but in the immediate wake of the blockbuster deal between the Heat and Bucks, things aren’t looking so great for Boston.

The Celtics’ level of interest in this deal wasn’t clear until the last week or so, when it became clear they were involved, and things escalated on Monday when multiple sources came out and indicated that they were all in on the Greek Freak.

And still, they lost out. They reportedly offered Jaylen Brown and two first-round picks, and still couldn’t get the deal done, creating a potentially fractured locker room in the process. 

Celtics have to get to work on busy offseason

Brad Stevens and his front office have certainly earned the benefit of the doubt, but it’s hard to understand getting this deep and not finishing the job. Once you’ve put Brown, your 29-year-old homegrown superstar, franchise icon, and Finals MVP, on the table, you simply have to get the deal across the finish line.

Coming back with egg on your face and Giannis in South Beach is just a brutal, brutal look for the Celtics. How are they supposed to explain this to JB? How are they supposed to explain this to the fans? Did the deal really fall apart because of Brad’s unwillingness to include Hugo Gonzalez? Could he have added another pick or swap to get it done? 

Celtics must repair relationship with Brown or trade him

Sure, that may have seemed like an overpay, but when you’re this far down the rabbit hole, it’s extremely damaging to come up short, and that’s what the Celtics did. Now Brown may be unhappy, Hugo unfairly has a target on his back, and for the first time in his tenure, Brad Stevens may be under the microscope.

Perhaps this all works out. Maybe Giannis will break down in a few years, and this will look like a dodged bullet. Maybe Brown is unbothered by the trade talks, and this fuels him to come back better than ever. Maybe Brad was just trying to drive up the price for Miami all along.

But in the moment, it looks like they went for it and failed. Now Brad has a mess to fix, and he better get to work on his backup plan in short order, which now has to start with figuring out what to do, if anything, with Brown. It’s a bad situation, but a salvageable one for Stevens and his team, as they are suddenly facing a pressure-packed, tumultuous offseason, with the end of the Jayson Tatum-Jaylen Brown era hanging in the balance. Your move, Brad.

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