This is a pivotal trade deadline for the Portland Trail Blazers franchise for several reasons, one of which is that their fate is closely tied to the Milwaukee Bucks. Thanks to the blockbuster Damian Lillard deal that backfired, Milwaukee still owes Portland a 2029 first-round pick as well as two first-round pick swaps in 2028 and 2030. Those are becoming increasingly valuable as the Bucks absolutely reek of desperation to upgrade their roster at the deadline.
The Eastern Conference is weaker than ever, yet the Bucks find themselves outside the playoff picture with an 18-25 record. This season has tested superstar Giannis Antetokounmpo's loyalty, as he's had every reason to request out of this messy situation that doesn't appear to be getting better anytime soon.
Giannis has made it clear that he's not the type of player to request a trade, but Blazers fans know that story all too well. Lillard remains one of the most loyal superstars in the league and never wanted to leave Portland, but failed attempts to upgrade the roster finally reached a breaking point.
There are striking similarities between the two superstars' situations, but with Giannis being a top-five player in the world, the spotlight is even more on Milwaukee than it ever was on Portland.
The Milwaukee Bucks reek of desperation
Despite Giannis being adamant about staying in Milwaukee, trade rumors continue to spiral. He's not doing himself any favors either, with comments like calling out "selfish" teammates after their blowout loss to the Thunder.
The Bucks can't really upgrade their roster even if they wanted to. And let's be clear, they do want to. They're aligned with their disgruntled superstar in that aspect. But with the Lillard trade backfiring, a questionable Kyle Kuzma trade, and then the decision to waive and stretch Lillard to bring in Myles Turner, Milwaukee is running out of options.
They'll make a move at the deadline. They essentially have to. And that's why this is a perfect situation for Portland.
The Bucks were rumored to go "big game hunting" (subscription required) at the deadline, yet the names NBA insider Jake Fischer includes overpaid players like Zach LaVine and Jerami Grant. Talented, but very expensive for non-needle movers. That's the only way the Bucks can upgrade their roster at this point, taking on misfits.
After this inevitable desperation move, it will be that much harder for Milwaukee to pivot. In other words, this could be the tipping point where Giannis ultimately decides he's had enough, realizes he no longer wants to waste the remaining years of his prime, and requests a trade in the offseason. That would give Portland leverage to either come away with a key piece in that deal as a facilitator or increase the value of those picks they hold onto.
In all likelihood, Giannis will stay in Milwaukee through the trade deadline. That doesn't mean he'll still be there when those picks begin to convey in 2028. And Milwaukee's desperation moves to keep him now could ultimately push him towards requesting a trade later.