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Blazers' dream Giannis trade becomes more real by the day

Tom Dundon's first offseason just got a lot more interesting.
Apr 10, 2026; Milwaukee, Wisconsin, USA;  Milwaukee Bucks forward Giannis Antetokounmpo looks on during warmups prior to the game against the Brooklyn Nets at Fiserv Forum. Mandatory Credit: Jeff Hanisch-Imagn Images
Apr 10, 2026; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Giannis Antetokounmpo looks on during warmups prior to the game against the Brooklyn Nets at Fiserv Forum. Mandatory Credit: Jeff Hanisch-Imagn Images | Jeff Hanisch-Imagn Images

The Portland Trail Blazers could make a huge swing in their first offseason under new owner Tom Dundon. At the top of the star list is Milwaukee Bucks forward Giannis Antetokounmpo.

"When it comes to Dundon's first NBA offseason in charge, I've heard from multiple league sources that the Blazers are expected to emerge as a prime trade suitor for Milwaukee's Giannis Antetokounmpo," NBA insider Jake Fischer recently reported on The Stein Line.

Fischer adds that Portland registered interest in Giannis at February's trade deadline (subscription required), but teams around the league concluded that Milwaukee wasn't going to make such a significant roster overhaul despite its slow start to the season.

Blazers have all the pieces to pull off a Giannis blockbuster

The Bucks should seriously consider changing their stance on Giannis this summer, as they find themselves in no-man's land. They've made several desperation moves to keep Giannis around, most notably waiving and stretching Damian Lillard to clear space for Myles Turner last summer. Milwaukee keeps digging itself a deeper hole, and it would be in the best interest of both Giannis and the franchise to go their separate ways.

Talks will inevitably resume this summer, and the Blazers are in a prime position to capitalize. Thanks to the blockbuster Lillard trade, Portland finds itself in the driver's seat of the entire Giannis sweepstakes. The Bucks would be wise to completely rebuild their roster from the ground up, but that becomes much more challenging unless they can recoup their future draft capital.

Portland was previously linked as a potential facilitator in a multi-team deal, coming away with a star from whatever team ultimately lands Giannis. However, these recent reports suggest that the Blazers should be taken much more seriously as a threat to land Giannis themselves.

They have just about everything required to pull off the summer blockbuster and finally elevate the ceiling of this rebuilding roster:

1) The former teammate connections to Giannis in Lillard and Jrue Holiday. 2) A combination of draft capital, young assets, and veterans to not only get the deal done but also remain competitive in terms of maintaining their depth. 3) A new owner willing to pay for retaining the team's players, despite his "cheap" reputation of cutting corners elsewhere. 4) A young core that has proven ready to make that next jump for a deep playoff run, as evidenced by their 42-40 record and seventh-seed finish this year.

Two roadblocks still stand in the way

Portland has suddenly climbed up the Giannis rankings, going from a sneaky dark horse to a legitimate threat. Still, two things are getting in the way of making this a reality.

For one, the Blazers are only interested in trading for Giannis if they can convince him to stay long-term. Portland runs the risk of a one-year rental should he decline his player option in 2027-28, and they understandably want assurance they wouldn't sacrifice so many assets for such a short-term move.

Additionally, there's the question of Blazers general manager Joe Cronin's willingness to go all-in. At his exit interview, Cronin mentioned he's willing to trade for a star but that it must be the right price, adding he won't sacrifice their entire future.

They would likely have to sacrifice a good portion of their youth in order to land a top-five player in the world. Does Portland really want to break up its young core after the progress it's shown over the past few years? Having the Bucks' picks certainly helps give them tremendous leverage, but it would likely cost a few young assets as well.

Either way, a Giannis trade is closer than it's ever been.

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