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BOSTON, MASSACHUSETTS - NOVEMBER 08: Jayson Tatum #0 of the Boston Celtics reacts after a dunk against the Brooklyn Nets during the fourth quarter at the TD Garden on November 08, 2024 in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Brian Fluharty/Getty Images)

The NBA offseason is heating up, and the Boston Celtics will be faced with a pivotal decision regarding their future as well as the future of one of their main stars.

Boston is reportedly exploring ways to acquire Milwaukee Bucks superstar Giannis Antetokounmpo, which could involve moving All-Star forward Jaylen Brown to a third team.

According to MassLive’s Brian Robb, Boston’s interest in Antetokounmpo may force it to chase realistic Brown trade options. 

The Portland Trail Blazers have been linked to be that third party to help the Celtics get their hands on Antetokounmpo. 

In the proposed three-team framework, the Blazers send Jerami Grant and Shaedon Sharpe, along with swap rights on Milwaukee’s first-round picks from 2028-2030, to the Bucks. In return, Antetokounmpo would head to Boston, with Brown landing in Portland.

“The Celtics obviously value Brown quite highly coming off his best regular season during his 10 years in Boston,” Robb wrote. “Yet, with Brown’s trade value potentially at its highest since signing a supermax contract, it’s understandable that Boston may want to explore what the All-Star could fetch in a hypothetical deal, whether that’s as a path to ultimately land Antetokounmpo or to reshape the roster in other ways.”

This framework leverages Portland’s assets from prior dealings with Milwaukee, particularly those tied to the Damian Lillard trade.

How the Celtics Can Make This Work

GettyMILWAUKEE, WISCONSIN – JANUARY 11: Giannis Antetokounmpo #34 of the Milwaukee Bucks is defended by Jayson Tatum #0 of the Boston Celtics during a game at Fiserv Forum on January 11, 2024 in Milwaukee, Wisconsin. The Bucks defeated the Celtics 135 – 102.

Moving Brown is not high on the Celtics offseason plans, but their ambitions to land Antetokounmpo will force their hands. There is simply no space to accommodate him as well as Brown and Jayson Tatum without severe cap constraints. 

Antetokounmpo and Brown are a very close fit salary-wise, but because of Boston’s lack of assets, a third team like Portland is likely needed to make the Milwaukee trade. The Blazers make sense for obvious reasons majorly due to the past dealings with both the Celtics and the Bucks.

“Brad Stevens has done plenty of dealing with the Blazers in recent seasons, acquiring Jrue Holiday from Portland in 2023 and trading him back there in June 2025,” Robb added. “Logically, the Blazers line up nicely as a third team in a Giannis Antetokounmpo swap since they own either draft picks or swaps with the Bucks from 2028-2030.”

Whether or not this pitch will beat other offers remains to be seen, but from a Bucks standpoint, they get pieces as well as draft assets, which is what they reportedly want in order to trade their two-time MVP.

What This Deal Means for Jayson Tatum and the Celtics

GettyBOSTON, MASSACHUSETTS – APRIL 28: Jayson Tatum #0 of the Boston Celtics reacts to a foul against the Philadelphia 76ers during the second quarter in Game Five of the First Round of the NBA Eastern Conference Playoff at TD Garden on April 28, 2026 in Boston, Massachusetts.

Moving on from Brown may not be as easy as it seems for the Celtics. He is a former Finals MVP and embodies everything Boston stands for. However, if it came down to him and Tatum being moved, he was always speculated to be the one. 

Brown’s availability at peak value is not one the franchise will look down on, especially with Antetokounmpo in the market. Portland is a decent destination as it made the playoffs this year and will gain a proven All-Star in Brown to accelerate its timeline. 

The Blazers aren’t the only option for a third team for the Celtics, but the pitch involving them looks like one everyone can benefit from.

Getting Antetokounmpo should be the only explainable reason to trade Brown, as it represents a massive swing for contention. The duo of Tatum and Antetokounmpo would be physical and dominant in almost every position on the floor.