Many around the league have circled the Portland Trail Blazers as potential buyers this Trade Season. The pipe dream has always been Milwaukee Bucks superstar Giannis Antetokounmpo. Should Milwaukee ultimately trade the Greek Freak, they'd desperately want their picks back from Portland so that they can effectively initiate a rebuild. That instantly made Portland a dark horse in the Giannis Sweepstakes.
The primary issue, however, is that Giannis was rumored to have "zero interest" in coming to Portland. Not surprising, as he's reportedly seeking a bigger market. That appeared to have taken Portland out of the running, with their only option being to facilitate a trade that sends Giannis elsewhere.
While being the middleman remains the most likely outcome, you still can't entirely rule them out of winning the main prize. Despite the slim odds of Giannis agreeing to an extension to stay in Portland, that hasn't deterred the Blazers from expressing their own interest in acquiring him, Marc Stein and Jake Fischer recently reported on The Stein Line (subscription required).
"The Stein Line has learned that Portland has also expressed its own interest to the Bucks that it would like to acquire Antetokounmpo ... even as the Blazers realistically understand that it would be an extreme longshot to convince Giannis to sign a contract extension that keeps him in the Pacific Northwest."
Blazers pursue Giannis despite his disinterest in Portland
They add that it's still much more likely the Blazers facilitate a Giannis trade and come away with an "impact veteran (or two)." Mikal Bridges is a name that continues to get brought up in these rumors, with the possibility of Portland moving Jrue Holiday to New York.
The Knicks and other teams reportedly believe that landing Giannis' former Bucks teammate would improve the odds of Giannis eventually coming too. That's an excellent position for Portland to be in as it increases Holiday's trade value leading up to the deadline (despite his poor production as of late).
At the same time, having Holiday could be why Portland feels more inclined to get involved in the Giannis trade talks. Having both Holiday and Damian Lillard could give them at least some shot at retaining Giannis long-term, especially since he's shown incredible loyalty throughout his career. The Blazers would also become legitimate contenders at that point, making a compelling case for him to overlook the small market.
Giannis has a $62.8 million player option in 2027-28, so there's certainly risk involved in the Blazers acquiring him. It's very possible that he'd turn out to be just a 1.5-year rental. But Blazers general manager Joe Cronin has made bold bets with this roster that have paid off in the past. Maybe Giannis is the next gamble worth taking.