The Portland Trail Blazers have already won the Damian Lillard trade with the Milwaukee Bucks. It's come full circle, as Portland somehow received the assets from the trade while also getting Lillard back two seasons later.
It was a long two seasons without arguably the franchise's best player of all time, but Portland's rebuild is in a much better position. That's part of the reason Lillard decided to return to Portland; he was adamant it was a "basketball decision."
Bucks dig themselves a deeper hole with desperate attempts to keep Giannis
Milwaukee's decision to waive and stretch Lillard to clear space for Myles Turner has backfired. Ever since winning a championship in 2021, it's been one bad decision after another -- many of which were catalyzed by their desperation to keep superstar Giannis Antetokounmpo around.
It feels like we're finally at a breaking point in the Giannis trade rumors. Nothing materialized at the deadline, but a blockbuster of the magnitude was always more likely to happen in the offseason anyway. That's when teams have much more roster flexibility, especially if it's a multi-team deal.
Portland is in the driver's seat of the entire Giannis sweepstakes, thanks to that lopsided Lillard deal. In fact, Bill Simmons recently ranked them as the second most likely landing spot for Giannis this summer, only behind the New York Knicks.
We wouldn't go that far, seeing as Giannis has no desire to come to Portland. But it does add fuel to the speculation that Portland is being considered a dark horse, given Jrue Holiday and Lillard's connections to Giannis, new owner Tom Dundon's hands-on approach, and, of course, the Bucks' draft capital.
Blazers hold the key to the entire Giannis sweepstakes
Milwaukee should initiate a full-on roster teardown if Giannis is ultimately moved. They can't effectively accomplish that without their own picks, as they'd have no incentive to bottom out. That gives Portland tremendous leverage this summer, which they are bound to capitalize on one way or another.
They can trade for Giannis himself, attempting to convince him to stay beyond just one season. Or, they could facilitate a Giannis blockbuster, coming away with a key piece from whatever team lands him. Mikal Bridges was one name that was thrown around at the deadline, although the Bucks' picks are more valuable than that.
The good news is, should Portland decide the picks hold more value than any player they can get, they can simply do nothing. They have an unprotected first-round pick in 2029 and swaps in 2028 and 2030. Those are looking increasingly valuable, especially with recent reports that Giannis and Milwaukee are not on the same page regarding his injury.
A disgruntled Giannis is exactly what Portland wants heading into the summer.