Bill Simmons recently called the Portland Trail Blazers a "wild card" team to watch over the offseason.
"The seatbelt is off with the Blazers the next three months," Simmons said on The Bill Simmons Podcast. "I am prepared for anything: Giannis trade, new coach, maybe they bring in a coach/GM. Any sort of wheeling and dealing. This new owner coming in who already has his proven thing from hockey of 'I'm coming in, I'm rolling up my sleeves, let's go.' I just think they're the wild card team this year."
Everything appears to be aligning at this stage in their rebuild. Portland has a new owner, Tom Dundon, taking over right when their young core is ready to make a legitimate playoff push. Throw Damian Lillard's highly anticipated return into the equation, and everything is on the table for a team with tremendous flexibility given their intriguing blend of youth and veterans.
Blazers set the stage for the most important offseason of their rebuild
Simmons also adds that the Blazers should be a dark horse in the Giannis Antetokounmpo sweepstakes this offseason. It's easy to see the connection: former teammates, the Bucks' draft capital, promising young assets, and an ambitious owner.
However, Giannis has also made it clear that he has no desire to come to Portland. The risk of taking him on in the offseason is heightened, as it could be a one-year rental if Giannis were to decline his $62.8 million player option in 2027-28. Dundon has a reputation as an aggressive owner, but he is more calculated than some may think, given his meticulous, analytical approach.
That said, a Giannis blockbuster in the offseason is becoming increasingly likely given the recent drama surrounding the Bucks and their superstar. It wouldn't be surprising to see Dundon and the Blazers capitalize on that situation as a facilitator in a multi-team deal, cashing in on some of that draft capital to come away with a star of their own.
But if there's one thing we've learned about the Blazers front office, it's to expect the unexpected. Nobody saw them coming away with Damian Lillard, Jrue Holiday, or Yang Hansen this past summer. And we could see even more surprising fireworks this offseason, with a new owner coinciding with a young core that's finally ready to compete.