Giannis Antetokounmpo continues to be linked with almost every contender as questions about his future in Milwaukee grow louder. The Boston Celtics are no exception. After an early playoff exit raised fresh questions about the roster, many have wondered whether Boston could emerge as a serious landing spot for the two-time MVP. However, one prominent insider believes the Celtics may be looking at the situation very differently.

During a recent episode of his podcast, Bill Simmons shared what he believes is Boston’s current thinking. While Giannis remains one of the most attractive trade targets in basketball, Simmons does not believe the Celtics are eager to reshape their roster through a straightforward superstar-for-superstar swap.

“If the Celtics trade Jaylen [Brown], I don’t think it’s going to be for Giannis. I think it’s going to be a trade like, multiple pieces, more flexibility, guys that would lead to one extra move after this. And I think that’s what they’re thinking,” Simmons said.

The financial side of any potential deal only complicates matters further. Giannis is set to earn roughly $58.4 million during the 2026-27 season and could become eligible for a four-year extension worth approximately $275 million in October. Boston already has massive long-term commitments tied to Jayson Tatum’s supermax contract and Jaylen Brown’s own record-setting extension, leaving very little room for roster flexibility.

While Brown’s salary could theoretically help match Giannis’ contract, Boston’s broader cap situation makes any blockbuster trade difficult. The Celtics are carrying more than $224 million in salary commitments and remain one of the league’s most expensive teams, limiting their ability to make major moves without creating additional complications elsewhere on the roster.

That reality is one reason Simmons believes Boston may prioritize flexibility over a splashy headline move. Rather than exchanging one cornerstone for another, he suggested the Celtics could be more interested in a deal that creates future options, adds depth, and potentially sets up another move down the road.

Meanwhile, a recent report from The Athletic’s Sam Amick and Eric Nehm painted a fresh perspective on Giannis’ next destination. For the longest time, many voices around the league believed that the 31-year-old would choose the Miami Heat. But “He’s very intrigued with the prospect of joining a Celtics team that, by any objective measure, is deeper and more dynamic than Miami’s,” the report said. “Antetokounmpo’s focus on getting back to title contention should not be overlooked.”

However, realistically speaking, the hurdle lies with Boston. The Celtics could still explore a route to land Antetokounmpo while keeping Jaylen Brown, since Jayson Tatum remains untouchable. Pairing a fully recovered Tatum with Giannis, plus key returners such as Derrick White and Payton Pritchard, could create one of the league’s toughest lineups. But that circles back to the bigger discussion…

Is Giannis Antetokounmpo a better fit than Jaylen Brown?

Any discussion about a potential Brown-for-Giannis framework eventually leads to the same question: which player gives a contender the better chance to win a championship? From a pure talent standpoint, the answer is difficult to debate. Giannis remains one of the most dominant players in basketball and belongs in the small tier of superstars capable of changing a franchise’s ceiling overnight.

Brown remains an elite talent, but Antetokounmpo has established himself among the game’s very best. Sure, Jaylen Brown played an MVP-caliber 2025-26 season, averaging 28.7 points, 6.9 rebounds, and 5.1 assists. But few players in the league have ever possessed the blend of size, power, reach, and mobility that Giannis brings to the floor. He functions in a category that stands apart from nearly every other superstar in NBA history.

Celtics president Brad Stevens indirectly highlighted why a player like Giannis is so appealing. Reflecting on Boston’s season, Stevens admitted the team struggled to consistently create quality looks and generate pressure at the rim. “One of the things that we’ve got to figure out is how to have more of an impact at the rim,” Stevens said. Few players in NBA history attack the basket with the force and consistency that Giannis brings, making him a natural theoretical fit for the issues Boston is trying to solve.

Giannis may check many of the boxes Boston is looking to address, but according to Simmons, that does not mean the Celtics are preparing an all-in pursuit. The financial hurdles remain significant, and the organization’s preference appears to be maintaining flexibility rather than reshuffling its core around another max contract. For now, Giannis remains an intriguing possibility rather than an imminent target.