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BOSTON, MASSACHUSETTS - MAY 02: Jaylen Brown #7 of the Boston Celtics handles the ball against the Philadelphia 76ers during the third quarter in Game Seven of the First Round of the NBA Eastern Conference Playoffs at TD Garden on May 02, 2026 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 Maddie Meyer/Getty Images)

The Boston Celtics’ Jaylen Brown question did not end when Giannis Antetokounmpo landed elsewhere.

Bleacher Report’s Grant Hughes proposed a Celtics-Trail Blazers trade that would send Brown to Portland in exchange for Jrue Holiday, Jerami Grant, Milwaukee’s 2028 first-round pick and Orlando’s 2028 first-round pick. Hughes noted that Portland would likely need to include both picks because of the money attached to Grant and Holiday, while Boston could reasonably ask for more.

That is the right starting point for the Celtics conversation.

Holiday’s return would be easy to sell emotionally. Grant would give Boston another veteran forward. Two future first-round picks would restock some of the draft capital a contender always needs.

But if Brown is truly available after Boston’s failed pursuit of Antetokounmpo, this is the kind of deal that should make the Celtics hesitate.

Jaylen Brown Trade Rumors: Celtics Would Get Useful Pieces, Not a Replacement

Holiday is the most interesting part of the proposal from Boston’s perspective.

He already knows the Celtics’ system, helped them win a championship and would immediately restore some defensive toughness and ball security. There is no mystery about whether Holiday can function in a playoff environment next to Jayson Tatum, Derrick White and Boston’s remaining core.

That does not make him a Brown replacement.

Brown is still a five-time All-Star and the 2024 NBA Finals MVP. The 29-year-old averaged a career-high 28.7 points last season while Boston finished 56-26 despite playing most of the year without Tatum. Moving that player for two veterans and future picks would be a franchise-shaping decision, not a minor pivot.

His contract makes any trade even more significant: he is entering the second season of a five-year, $286.2 million supermax extension that runs through 2028-29.

Grant also makes basketball sense in theory. He is a big wing who can score, space the floor and guard multiple frontcourt matchups. But Boston would have to decide whether he is a clean fit next to Tatum or just an expensive substitute for a much better version of the same archetype.

That is the flaw in the package. It gives Boston useful players. It does not clearly give Boston the best player in the deal, the cleanest salary sheet or a new young cornerstone.

Brad Stevens’ Comments Keep the Door Open

Celtics president of basketball operations Brad Stevens tried to steady the conversation around Brown after Boston missed on Antetokounmpo.

Stevens said Brown remains “a big part of us,” according to Reuters, after multiple outlets reported that Boston had offered Brown as part of a package to Milwaukee before Antetokounmpo went to Miami.

That matters. It is also not the same as declaring Brown untouchable.

The New York Post characterized Stevens as noncommittal on Brown’s long-term future in the fallout from the Giannis talks. CelticsBlog similarly noted that Stevens praised Brown and emphasized communication, but did not definitively rule out future trade possibilities.

That leaves Boston in an awkward middle ground. The Celtics can say they value Brown, and that may be completely true. But once a star is included in serious trade talks, rival teams tend to keep calling.

Portland appears to be one of the teams worth watching.

Celtics Should Ask Blazers for More

The cleanest Celtics takeaway is not that the Blazers are a bad trade partner. It is that this proposal should probably be treated as an opening framework.

If Boston is moving Brown to Portland, the Celtics should want either a cleaner financial structure, a more compelling young player or more draft compensation. Hughes acknowledged that asking for a third pick or a salary other than Grant would be reasonable. That feels especially true from Boston’s side.

The Celtics are not rebuilding as long as Tatum is their franchise centerpiece. A Brown trade would need to help Boston contend now or set up the next title team around Tatum.

Holiday and Grant only partially serve the first goal. The picks only eventually serve the second.

That is why Portland names such as Donovan Clingan, Toumani Camara or Shaedon Sharpe would likely matter in any serious Celtics conversation. The Blazers would resist that, but Boston does not have to make Portland comfortable. Sharpe especially seems like a piece the Celtics need, and Portland would be willing to part with.

If Brown is on the table, the Celtics need more than Holiday, Grant and two future picks. That package is credible enough to discuss. It is not strong enough to end the conversation.