The Portland Trail Blazers are hoping a Giannis Antetokounmpo trade materializes by the Feb. 5 trade deadline for two reasons:
1. The value of the 2028-30 Milwaukee Bucks draft capital the Blazers received in the Damian Lillard trade would drastically increase.
2. Portland could leverage that to come away with a key piece if they facilitate a Giannis trade.
Blazers could upgrade roster and increase value of Bucks picks in just one move
Portland owns Milwaukee's first-round pick swaps in 2028 and 2030 and has its first-round pick in 2029. Those would have a high likelihood of turning into lottery picks with Giannis out of the equation.
In large part because of their attempt to keep Giannis around, Milwaukee's future outlook looks grim. Their Kyle Kuzma trade backfired as he's quickly become a negative asset on a bad contract. But their most recent mistake dug an even deeper hole: waiving and stretching Damian Lillard to clear space for Myles Turner. That wasn't the needle mover they hoped for, and as a result, the Bucks are headed for purgatory, even with a top-five player in the world. They have limited options to pivot and upgrade their roster, leading Giannis to be open to a trade despite his loyalty.
The Bucks are seeking a combination of young players and draft picks to help initiate a rebuild in a post-Giannis era. They shouldn't be competitive by the time those picks begin to convey in 2028, which is an ideal situation for Portland.
One thing the Blazers must consider is that the Bucks wouldn't have an incentive to bottom out entirely if they didn't have control of their own draft. So, although the Blazers would benefit hugely from any Giannis trade, it could be in their best interest to diversify their investment by giving at least some of that draft capital back to Milwaukee.
That's why it suddenly makes perfect sense for them to get involved in a multi-team trade. The Blazers are finally in a position to buy at the trade deadline, and the simplest way for them to upgrade their roster is to steal a piece from whatever team lands Giannis. Not only could they come away with someone like Jaden McDaniels, Mikal Bridges, etc., but they would also have more value in whatever Bucks picks they were able to hold onto.
The Blazers are in a unique spot in their rebuild as a team that wants to return to the postseason while prioritizing their long-term outlook. Coming away with a key piece by the deadline would address those short-term goals. Holding onto some of the Bucks' picks, whose value would increase with Giannis' departure and Milwaukee having an incentive to tank, would put them in a prime position going forward.
That's how Portland can turn a Giannis blockbuster into multiple wins.