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. And it’s simply because they’re sitting 2nd in the East with a 54-26 record. They started this season with a new roster and a lineup without Jayson Tatum. Well, now they are in a position where a title dream doesn’t seem too far-fetched. However, if that run doesn’t come to fruition, what will they do?

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, general manager Brad Stevens has done everything to add more star power to the Celtics’ roster. He brought back Al Horford in 2021. Added Malcolm Brogdon, Jrue Holiday, Kristaps Porzingis, and Derrick White. And also handed Jaylen Brown a five-year, $285.4 million supermax contract extension in 2023. That’s not all, he also secured Jayson Tatum’s future in 2024 with a 5-year, $314 million supermax contract extension.

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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 further 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 any one of these four teams: Charlotte Hornets, Philadelphia 76ers, Orlando Magic, or Toronto Raptors. Well, many believe that the first playoff series is going to be easy for the Cs. However, don’t take the Hornets lightly; they have emerged as a bigger threat due to their shooting and offense.

But the real challenge will emerge in the second leg of the postseason. Last year, Jayson Tatum & Co. had to say goodbye to their title contention against the New York Knicks in this very Round 2 of the playoffs. That, and JT’s Achilles injury, triggered a chain reaction within the organization. They traded Jrue Holiday to Portland, let go of Big Al in free agency, and gave KP to the Hawks.

Therefore, it won’t be surprising if the front office trades for Giannis Antetokounmpo and gives away Jayson Tatum or Jaylen Brown. But again, the question remains the same: Why would they break this unbeatable pair? One could say the Greek superstar will add more explosive power on both ends. However, will the Celtics’ finances favor the trade?

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, Jaylen Brown is projected at $57.07M, eating up a hefty 34.59% of the cap. Stack that against Boston’s sheet: $224.2M already committed and a glaring -$59.2M cap space. Now, here’s where it gets interesting.

Matching Giannis’ $58.4M is technically clean if Boston parts with either Jayson Tatum or Jaylen Brown straight up. The money aligns almost dollar-for-dollar. However, apron rules hover like a strict referee. With just $24.07M below the first apron and $37.07M to the second, flexibility shrinks fast. Depth pieces, incentives, and bonuses start to matter more than ever.

So yes, it’s possible. But it’s also a gamble with sharp edges. Swap Jaylen Brown, and you bet on a Giannis-Tatum core. Move Jayson Tatum, and you hand the keys to Giannis-Brown. Either way, Boston reshapes its identity overnight. The real trigger, though, lies in the playoffs. Win big, and this fades away. Fall short, and the front office starts dialing.