Jaylen Brown Will Not Get Traded For Giannis Antetokounmpo, Per Bill Simmons

Giannis Antetokounmpo's future is one of the hottest topics heading into the offseason. Multiple teams, including the Miami Heat and Portland Trail Blazers, have been linked with him, with the Boston Celtics somewhat surprisingly entering the mix as well. But the most intriguing part of the rumor is that Boston could be willing to part ways with Jaylen Brown in an effort to bring the Greek Freak to TD Garden.

However, sportswriter and podcast host Bill Simmons doesn't think this will happen. He didn't oppose the notion of trading Brown at all. Instead, he believes that if the star wingman were to get traded, it would be a move that creates flexibility.

"If the Celtics trade Jaylen, I don't think it's going to be for Giannis," Simmons said on his podcast. "I think it's going to be a trade like this: multiple pieces, more flexibility, guys that lead to one extra move after this. I think that's what they're thinking."

Talent-wise, a Giannis Antetokounmpo-for-Jaylen-Brown deal makes the most sense. Basically, the Milwaukee Bucks and the Celtics would potentially be trading established stars who can lead a team to championships.

For the Bucks, that deal might make the most sense if they want to stay in contention after trading Giannis. Brown proved during the 2025-26 season that he could be a team's centerpiece, posting career highs in points (28 ppg), rebounds (7 rpg), and assists (6 apg) while Jayson Tatum spent most of the season sidelined due to an Achilles tendon tear.

Plus, Brown is a few years younger than Antetokounmpo. Acquiring him means Milwaukee won't have to trudge through another lengthy rebuild. With him, they're already a playoff team, and with a strong supporting cast, the Bucks might just become contenders in the playoffs again.

For the Celtics, though, moving Brown to create flexibility might be a better move. They could be looking to retool around Tatum, and sacrificing one star to fast-forward the process is a high-risk, high-reward gamble.

That said, they've done this before. Back in 2013, they traded aging stars Kevin Garnett and Paul Pierce to the Brooklyn Nets for role players and three future first-round picks.

Two of those draft picks turned into Jaylen Brown and Jayson Tatum, who co-led the team to the 2024 title.

Celtics emerge as one of Giannis' preferred destinations

The Giannis Antetokounmpo trade discussions have had the league in a chokehold for quite some time now. Over its course, the teams being mentioned as potential destinations have grown or changed.

Initially, there were reports that he was exclusively interested in joining the New York Knicks. Since then, that list has grown quite a bit.

Reports have stated that Giannis would prefer to stay in the Eastern Conference. Most people believe that because of this, the Miami Heat are the favorites to win this arms race. Then there's the Portland Trailblazers in the West, where a reunion with Damian Lillard (who spent 24/25 in Milwaukee) could be on the cards. A healthy Dame and a motivated Giannis together on the same team could spell trouble for rivals in the best.

But the Heat remain a clear favorite. Not only do they have attractive tradeable assets like Tyler Herro, Jaime Jaquez Jr., Kel'el Ware, and future first-round draft picks, but Florida is also reportedly a Giannis-preferred destination.

“Hey, Miami’s not a bad place, man. It’s a beautiful, beautiful city, beautiful city,” Giannis said in an interview on Gogis Garage earlier this year.

While the Heat have been a clear favorite, the Celtics have flown under the radar. The Celtics have an established championship-winning core. They have depth, excellent coaching, and an established superstar in Tatum, who's now healthy and ready to compete for a ring again next season. Things that are "intriguing" to Giannis, as reported by The Athletic.

While the Bucks can technically trade him anywhere, Giannis does have more control over the situation. He has a player option for 2027-28, so while Milwaukee can trade him anywhere, he could just decide to decline that option.

The idea that he could just become an unrestricted free agent if he doesn't like where he's traded to should be enough to scare teams away from forcing a trade.