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No-brainer 3-team Jaylen Brown trade is too good for Blazers to refuse

Portland could land Jaylen Brown by facilitating a Giannis Antetokounmpo trade.
Apr 26, 2026; Philadelphia, Pennsylvania, USA; Boston Celtics guard Jaylen Brown (7) during warmups against the Philadelphia 76ers at Xfinity Mobile Arena. Mandatory Credit: Eric Hartline-Imagn Images
Apr 26, 2026; Philadelphia, Pennsylvania, USA; Boston Celtics guard Jaylen Brown (7) during warmups against the Philadelphia 76ers at Xfinity Mobile Arena. Mandatory Credit: Eric Hartline-Imagn Images | Eric Hartline-Imagn Images

The Portland Trail Blazers are in a prime position to facilitate a multi-team Giannis Antetokounmpo trade. While it's unlikely they acquire Giannis directly because of his lack of interest in coming to Portland, the Blazers are still in the driver's seat to come away with a star of their own.

The future Bucks pick they acquired in the Damian Lillard deal gives Portland significant leverage, as Milwaukee will certainly want to recoup those picks to retain control over its own future. As of now, the favored landing spot is likely the New York Knicks, meaning Portland could potentially come away with someone like Mikal Bridges or Karl-Anthony Towns. That said, the Boston Celtics, fresh off a disappointing first-round playoff exit, shouldn't be overlooked.

Celtics are a dark horse in the Giannis sweepstakes

If that hypothetical does play out, it gives Portland a chance to land former Finals MVP Jaylen Brown.

Here's what a potential three-team trade could entail:

Boston Celtics receive: Giannis Antetokounmpo

Portland Trail Blazers receive: Jaylen Brown

Milwaukee Bucks receive: Scoot Henderson, Shaedon Sharpe, Jerami Grant, Portland's 2028 first-round pick swap rights returned, Milwaukee's 2029 unprotected first returned, Milwaukee's 2030 swap rights returned, 2027 first-rounder (via Boston)

An Antetokounmpo-Brown framework makes sense for the Celtics, who could look to upgrade their star power. It doesn't make sense for the Bucks to downgrade for Brown, considering they'd want to initiate a full-on roster teardown and rebuild in a post-Giannis era.

Why the Blazers would do this trade

That's where Portland comes in as the ideal facilitator. Not only do they give the Bucks their picks back from 2028-30, but they also give them a foundation to build on with an up-and-coming backcourt of Scoot Henderson and Shaedon Sharpe.

Losing the first two first-round picks of Portland's rebuild would certainly sting, but that's the reality of this two-timeline approach they have put themselves in. If the Blazers want to win now with the closing windows of aging stars Jrue Holiday and Damian Lillard, they'll need to sacrifice at least some of their future. General manager Joe Cronin mentioned in his exit interview that he's open to landing a star but isn't going to make an all-in move that would ruin Portland's long-term outlook.

This potential deal strikes a balance. Portland can make a deep playoff run with a starting unit of Lillard, Holiday, Brown, Deni Avdija, and Donovan Clingan. They also still have a promising future by retaining key building blocks, including Avdija, Clingan, and Toumani Camara.

While Henderson and Sharpe have each shown flashes of their respective high ceilings, Portland suddenly has an increased sense of urgency to win now. It could be in their best interest to move on from the future backcourt duo that has yet to put it all together on a consistent basis.

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