Damian Lillard Trade Fallout: Bucks' Desperation Fuels Blazers' Future

Everythiiing

Jan 24, 2026 • 3 min read

Damian Lillard dribbling a basketball on a basketball court

The Aftermath of the Damian Lillard Trade

The NBA trade deadline has always been a period of intense speculation and strategic moves, but this year, the situation surrounding the Milwaukee Bucks and the Portland Trail Blazers has added a unique layer of complexity. At the center of it all is the Damian Lillard trade, which initially seemed like a blockbuster move but has since backfired, leaving both teams in precarious positions.

Portland's Valuable Assets

As a result of the Lillard trade, the Milwaukee Bucks now owe the Portland Trail Blazers a 2029 first-round pick, along with two first-round pick swaps in 2028 and 2030. These picks have become increasingly valuable as the Bucks find themselves in a desperate situation to upgrade their roster. The Eastern Conference is weaker than ever, yet the Bucks sit outside the playoff picture with an 18-25 record.

Giannis Antetokounmpo's Dilemma

Superstar Giannis Antetokounmpo's loyalty has been tested this season, with every reason for him to consider a trade out of Milwaukee. While Giannis has made it clear that he's not the type of player to request a trade, Blazers fans know the story all too well. Lillard, one of the most loyal superstars in the league, never wanted to leave Portland, but failed attempts to upgrade the roster finally reached a breaking point.

Striking Similarities

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. 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.

Bucks' Desperation Fuels Blazers' Future

The Milwaukee Bucks reek of desperation, and it's a situation that could ultimately benefit the Portland Trail Blazers. The Bucks have made several questionable moves this season, including the Lillard trade backfiring, a questionable Kyle Kuzma trade, and the decision to waive and stretch Lillard to bring in Myles Turner. These moves have left Milwaukee running out of options.

Desperation Moves at the Trade Deadline

The Bucks will make a move at the deadline; they essentially have to. They were rumored to go "big game hunting" at the deadline, yet the names NBA insider Jake Fischer includes are 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, by taking on misfits.

Potential Impact on Giannis

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.

Portland's Strategic Advantage

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. For the Portland Trail Blazers, this situation presents a strategic advantage.

Leveraging the Picks

As the Bucks continue to make desperate moves, the value of the picks they owe to Portland could increase. This could position the Blazers to make a significant move in the future, either by acquiring a key player or by strengthening their roster through the draft. The Blazers have shown loyalty to their superstar, and now they have the opportunity to leverage that loyalty into a stronger team.

The Future of Both Teams

The NBA trade deadline is a time of uncertainty and opportunity, and the situation between the Milwaukee Bucks and the Portland Trail Blazers is no different. As the Bucks continue to navigate their desperate situation, the Blazers will be watching closely, ready to capitalize on any opportunity that arises. The future of both teams hangs in the balance, and the outcome could have lasting implications for years to come.

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