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Deciding factor in Celtics' Giannis chase revealed if Bill Simmons is right

Bill Simmons says the Celtics' unwillingess to meet Giannis Antetokounmpo's extension demands cost them the superstar.
Apr 10, 2026; Milwaukee, Wisconsin, USA;  Milwaukee Bucks forward Giannis Antetokounmpo (34) looks on prior to the game against the Brooklyn Nets at Fiserv Forum. Mandatory Credit: Jeff Hanisch-Imagn Images
Apr 10, 2026; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Giannis Antetokounmpo (34) looks on prior to the game against the Brooklyn Nets at Fiserv Forum. Mandatory Credit: Jeff Hanisch-Imagn Images | IMAGN IMAGES via Reuters Connect

Wednesday’s blockbuster trade sending Boston Celtics star Jaylen Brown to the Philadelphia 76ers for Paul George, two first-round picks, and two second-round picks left Boston’s fanbase stunned.

In just under two weeks time, they’d gone from dreaming about landing Giannis Antetokounmpo, to coping with having traded Brown for George.

Sickening stuff.

Especially because it felt like the Celtics were the ones holding all of the cards in negotiations with the Milwaukee Bucks. The reporting throughout the day of Antetokounmpo’s eventual move to the Miami Heat indicated that, and when the news officially broke, it came as a surprise.

Multiple reports revealed that Boston had offered Brown and a pair of first-rounders to Milwaukee for their two-time MVP, but the Bucks were hoping to pry second-year wing Hugo Gonzalez from the Cs.

Boston wouldn't budge, per the reporting, and Giannis headed to South Beach.

Bill Simmons rubs salt in the wounds of Celtics fans

On Thursday, Bill Simmons hosted an emergency episode of The Bill Simmons Podcast on Netflix. He discussed the organization’s decision to trade Brown, among other things.

Simmons circled back to the Giannis saga. He shared that Boston’s negotiations with Antetokounmpo on a potential contract extension played a role in a deal falling through, as well.

“He didn’t sign off on the Miami trade for a couple of days there,” Simmons said. “They were talking about an extension with the Celtics. It came down to it either being for two years at 30% of the salary cap or three years at 35% of the cap, and the Celtics were pretty entrenched at two for 30 and Giannis wanted the three for 35. They couldn’t agree on it and that’s when he greenlit the Miami trade and Miami threw in [Kasparas] Jakucionis.”

Could Boston's unwillingess to give Giannis his desired extension have derailed their chances at landing him

Whether or not a Giannis to Boston trade would’ve happened had Boston been more willing to commit more long-term money to the 32-year-old remains a mystery, though.

At the point of said negotiations, was he only willing to greenlight a trade to the Celtics? That’s the only way that what Simmons is saying would’ve been the backbreaker in their discussions.

Throughout the arc of this story, we were all told it was between both Boston and Miami, not just down to one of them. The team’s unwillingness to include more assets (more justifiable before they traded Jaylen Brown seemingly just for fun), still seems to have been the final nail in their coffin.

The whole situation sucks because on paper, Boston was right not to come off of their offer or willingness to commit a supermax extension to an aging star. In practice, they wound up getting absolutely burned by their own burning desire to move off of Brown.

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