We’re nearing the end of the 2025–26 regular season. With just two games left on their slate, the Boston Celtics can savor their moment—they sit second in the East at 54–26 and look firmly in contention. They started this season with a new roster and a lineup without Jayson Tatum. Now, they’ve positioned themselves as a legitimate title threat. However, if that run falls short, what comes next?

Could the Celtics realistically team up with Giannis if it means parting ways with either Brown or Tatum? “We pick and choose when you decide to share stuff that you’ve heard. And that’s a tricky one because, like, how realistic is it? Well, right now they’re feeling great about what they’re doing,” NBA insider Sam Amick said on Run It Back. “Historically, they are a group that you could argue they pursue every superstar who’s available. That’s just kind of how their front office is wired with Brad Stevens leading the way.”

Since 2021, Stevens has aggressively reshaped the roster to maximize star power. He brought back Al Horford in 2021. He later added defensive anchor Jrue Holiday and versatile big Kristaps Porzingis, complementing a core that already included Derrick White. He also handed Brown a five-year, $285.4 million supermax extension in 2023 and secured Tatum’s future in 2024 with a five-year, $314 million deal.

You look at it and think—if they’re already winning, why even consider making this move? “Well, that’s just the league. And so I think it’s a matter of how did the playoffs go? Because you’re obviously correct that one of the Js would have to go,” Amick added. “And I think even some of this interest in the past has been born out of the fact like they didn’t know that Jaylen Brown was going to level up like he has and have the kind of year that he has. So we got to see how the postseason goes.”

The insider continued, “If they’re raising the trophy again, then obviously this noise, however much noise there is, is going to completely go away. If they get bounced in the second round, then, like any other team in that spot, they’re going to look at the landscape.”

Ultimately, everything comes down to the playoffs. In Round 1, they could face the Charlotte Hornets, Philadelphia 76ers, Orlando Magic, or Toronto Raptors. On paper, that matchup looks manageable, but teams like Charlotte have become dangerous with their perimeter shooting and offensive pace.

The real test would come in the second round of the playoffs. Last year, Tatum & Co. were eliminated in that stage by the New York Knicks, and Tatum’s Achilles injury only compounded the fallout. That stretch triggered major roster changes: Holiday was traded to Portland, Horford departed in free agency, and Porzingis was moved to Atlanta.

So, it wouldn’t be shocking if the front office at least explores a move for Antetokounmpo, even if it means sacrificing Tatum or Brown. But the central question remains: why break up a proven duo? Giannis would elevate the team’s two-way dominance, but the financial and roster implications are far from simple.

Will moving Jayson Tatum or Jaylen Brown be enough for Boston to acquire Giannis Antetokounmpo?

Numbers first, because they set the drama. Giannis Antetokounmpo is lined up for $58.4M in 2026–27, with a looming $275M extension window in October. Jayson Tatum sits right there at about $58.46M under his $314M supermax running through 2029–30.

Meanwhile, Brown is projected at $57.07M, accounting for roughly 34.59% of the cap. Boston already has $224.2M committed, leaving them deep into the luxury tax with virtually no cap space (-$59.2M).

A straight-up deal involving either Tatum or Brown works financially, as the salaries align almost perfectly with Giannis’ $58.4M figure. However, apron restrictions complicate matters. With just $24.07M below the first apron and $37.07M below the second, flexibility is limited. At that point, even smaller contract details, bonuses, role players, and incentives become critical.

So yes, a deal is possible, but it comes with significant risk. Swap Brown, and you build around a Giannis-Tatum core. Move Tatum, and the franchise shifts to Giannis-Brown overnight. Either path dramatically alters Boston’s identity.

In the end, the playoffs will decide everything. Win a title, and this speculation disappears. Fall short, and the front office may seriously consider a blockbuster move.