Boston Celtics

"I am not convinced he’s going to be on the team in October. I think it’s 50/50.”

By Conor Ryan

June 23, 2026 | 4:13 PM

3 minutes to read

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The Boston Celtics came up just short in the Giannis Antetokounmpo sweepstakes on Monday night.

But now that the Bucks dealt the two-time NBA MVP to the Heat in a blockbuster trade, what’s next for the Celtics, Brad Stevens, and Jaylen Brown?

While a core anchored by both Jayson Tatum and Brown should still keep Boston entrenched as contenders in the East, it remains to be seen how the Celtics move forward — especially with Brown reportedly dangled out as the headliner in a package for Antetokounmpo.

“So now, if you’re Boston, there is going to be fallout from this,” ESPN’s Shams Charania said during an appearance on SportsCenter. “[There will be] some hard conversations, because for the second time in four years the Celtics have offered Jaylen Brown, their co-star with Jayson Tatum, in a trade.”

Given how close the Celtics seemingly came to shipping out Brown — fresh off a season where he finished sixth in NBA MVP voting as Boston’s top scoring option — longtime Boston sports scribe and The Ringer founder Bill Simmons doesn’t believe that the Brown trade rumors are quieting down.

“I don’t think [the Celtics] would have entertained this at the end of the season,” Simmons said on the latest episode of his podcast. “I think something definitely shifted as we went along, and I am not convinced he’s going to be on the team in October. I think it’s 50/50.”

Simmons’ comments fall in line with new reports on Tuesday morning about Brown’s long-term future in Boston.

After coming up short in the bidding for Antetokounmpo, the Celtics are still reportedly willing to deal away Brown as they look to augment their roster around Tatum.

“Boston is in a situation where they have put to the whole world out there that Jaylen Brown, their Finals MVP, [was available],” ESPN reporter Brian Windhorst said on Tuesday. “They of course knew it was possible they were going to lose to Miami. They wanted to win, they made a very strong offer, but they were not willing to put their entire team in because on the other side of this trade they had to have a team.”

“So, now, what I expect to happen is a bidding war for Jaylen Brown [from] other teams in the league. In the most recent days, teams have been preparing for this eventuality that it wouldn’t be the Boston Celtics who won the Giannis sweepstakes and there would be a Jaylen Brown market.”

Fresh off a season where Brown earned Second Team All-NBA honors and averaged career-highs in points (28.7), rebounds (6.9), and assists (5.1),  Simmons wondered whether or not Brown might have a willingness to play elsewhere — especially if he can hold court as a team’s No. 1 option and leader.

“When Jaylen said that last year was the favorite year of his career last year and then tried to backtrack a little … I think a huge part of that was he finally got his shine as a real guy,” Simmons said. “I’m sure he loved to prove that you can still be a really good team if I’m your best player.

“They went 56-23 after going 0-3 to start the year. He proved it. We’ll see what else he wants to prove.”

In terms of potential contingency plans for the Celtics and Brown, Simmons tabbed both the Pelicans and Hawks as potential suitors — even if those returns wouldn’t match the outright star power generated by a player like Antetokounmpo.

“To me, the pivot would be looking at New Orleans,” Simmons said. “If they’re going to trade Jaylen and trying to get [Trey] Murphy and Herb Jones, or Murphy [and] Jordan Poole’s expiring [contract] and picks from the Pelicans, whatever version of that.

“Or the Hawks. I just feel like there are better trades than this for Giannis. I don’t know how Giannis and Tatum would have played together, and you’re talking about Giannis having health risks. Tatum’s coming off a torn Achilles. Like — I don’t think this trade was a slam dunk for them, and I’ve said this the
whole time.”