Giannis Antetokounmpo was ready to approve a trade to the Boston Celtics, but the deal fell through at the last moment when the two sides couldn’t agree on the extension that he wanted.
This was the latest bombshell revelation made by Bill Simmons on his podcast: that the trade wasn’t the biggest obstacle. But it was the contract demands.
“He didn’t sign off on the Miami trade for a couple of days because he was still discussing an extension with the Celtics. It ultimately came down to the extension. The Celtics were offering two years at 30% of the salary cap. Giannis wanted three years at 35% of the cap. Boston was pretty entrenched in its two-year, 30% offer. The two sides couldn’t reach an agreement. That’s when Giannis finally signed off on the trade to Miami.”
If what Simmons is saying is true, this is pretty stunning, detailing how the Celtics lost the plot in pursuit of their best players in the world. Giannis wanted to play for the Celtics, but he wanted a three-year extension worth $173.2 million. But Boston’s offer was approximately $99 million over two years.
The Celtics were not negotiating with another All-Star. They were talking with a two-time MVP, a Finals MVP and one of the best two-way players in the league.
But not even the most surprising part.
Jaylen Brown, the player whom the Celtics were planning to move, was already on a contract paying 35% of the salary cap. If the Celtics were willing to commit that level of financial commitment for Brown, questions arise as to why they wouldn’t do the same for Giannis.
And once the extension talks stalled, Giannis reportedly approved a trade to the Miami Heat instead. The Celtics eventually pivoted in a completely different direction, trading Brown after a massive fallout between the two sides. They sent him to the Philadelphia 76ers for Paul George and draft picks, a return that can be called subpar at best.
The Celtics could have had Giannis pairing with Jayson Tatum to form a new superteam. But instead, they ended up with Brown leaving for Philadelphia in a deal that brought back a 34-year-old Paul George and future draft assets.
Brad Stevens, who has been widely hailed as one of the best GMs in the NBA today and won the Executive of the Year award for the 2025-26 season, might have fumbled the bag here. But you should never count out the Celtics; they have been the most consistent team in the East for the past decade, and they could yet have a move or two that could put them back in the contender tier. However, this will go down as one of the biggest ‘What-if” moves in Celtics’ history.
Sometimes championship windows close because a team lacks the assets to make a trade. According to this report, the Celtics may have had the deal in place, but couldn’t bridge the final gap on the contract that mattered most.
