New Portland Trail Blazers owner Tom Dundon has made one thing clear about the franchise’s next phase.
Development is no longer the primary objective.
Winning is.
That reality is why the latest report from NBA insider Jake Fischer linking Boston Celtics star Jaylen Brown to Portland is generating attention around the league as the Trail Blazers enter what could be a pivotal offseason.
Speaking on Bleacher Report’s NBA Insider Notebook livestream Tuesday, Fischer identified Portland as one of several teams monitoring Brown’s situation in Boston.
“The Trail Blazers have had interest in Jaylen Brown dating back to Damian Lillard’s first tenure with Portland,” Fischer said. “By all accounts, whether it’s Giannis, whether it’s trying to go for Anthony Davis in Washington, the Blazers, under new owner Tom Dundon, do want to make aggressive trade moves this summer and try to get better.”
Fischer cautioned that Boston has not shown signs of actively shopping Brown.
“Until we actually hear that Boston is engaging in Jaylen Brown trade talk, all this stuff is just going to be teams calling and trying to see,” Fischer added.
Jaylen Brown Fits Portland’s New Timeline
Brown would represent exactly the type of established star Portland could pursue after Dundon publicly signaled a shift away from a rebuild.
“I think the focus that’s been the last few years — around development — is now around winning,” Dundon said during his introductory press conference. “It’s more fun to win.”
The timing is notable.
Portland improved from 21 wins in 2023-24 to 36 victories in 2024-25 before reaching 42 wins and a playoff appearance this season. Despite a first-round exit, the Trail Blazers believe they possess one of the Western Conference’s most promising young cores.
All-Star Deni Avdija headlines a roster that also includes Scoot Henderson, Shaedon Sharpe, Toumani Camara, Donovan Clingan and Yang Hansen. Veteran leaders Jrue Holiday and Jerami Grant remain under contract, while Damian Lillard is expected to return next season after recovering from an Achilles injury.
Adding a player of Brown’s caliber could dramatically accelerate Portland’s timeline.
The four-time All-Star averaged 28.7 points, 6.9 rebounds and 5.1 assists this season while helping Boston win 56 games despite Jayson Tatum missing significant time following Achilles surgery.
Trail Blazers Armed With Assets and Flexibility
GettyJaylen Brown battles Jerami Grant during a game between the Celtics and Trail Blazers. Portland has been mentioned as a potential suitor if Boston ever explores Brown trade scenarios this offseason.
One reason league executives continue connecting Portland to star players is the franchise’s growing collection of trade assets.
According to ESPN front office insider Bobby Marks, the Trail Blazers hold six tradable first-round picks beginning in 2027, along with multiple future Milwaukee draft assets acquired in previous deals.
Portland also enters the offseason approximately $31 million below the luxury tax and $39 million under the first apron, giving the organization flexibility to pursue upgrades through trades, free agency or both.
Fischer specifically noted Portland’s ability to utilize Jerami Grant’s contract and draft capital in larger multi-team constructions.
“If there is a Giannis trade, regardless of if he goes to Portland or not, the Blazers have an opportunity to send picks and figure out a way to get better in a multi-team capacity,” Fischer said.
Celtics Decision Remains Key
For now, Brown remains under contract in Boston and Celtics president Brad Stevens has publicly dismissed speculation regarding the star forward’s future.
Still, rival executives continue monitoring the situation closely.
And with Dundon promising a more aggressive approach, Portland appears positioned to be among the teams ready to make a call if one of the NBA’s biggest stars ever becomes available.
Whether that star is Brown or someone else, the Trail Blazers’ rebuilding phase may be nearing its end.
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