Damian Lillard trade keeps looking better and better for the Blazers

Portland's bet against Milwaukee looks better than ever.
Portland Trail Blazers Introduce Damian Lillard
Portland Trail Blazers Introduce Damian Lillard | Amanda Loman/GettyImages

The Portland Trail Blazers defeated the Milwaukee Bucks with a final score of 115-103. Both teams were shorthanded in this contest, but it gave the Blazers a glimpse of just how bad this Bucks roster is without Giannis Antetokounmpo. Milwaukee's superstar has missed three consecutive games due to a left adductor strain, and the Bucks unsurprisingly now have an active five-game losing streak.

Blazers general manager Joe Cronin bet against the Bucks' long-term outlook when he ultimately decided to trade Lillard to Milwaukee over his preferred landing spot with the Miami Heat. Let's revisit the deal that's becoming increasingly lopsided:

  • Bucks receive: Damian Lillard
  • Blazers receive: Deandre Ayton, Toumani Camara, Jrue Holiday, 2029 first-round pick (via Bucks), two first-round pick swaps (via Bucks, 2028 and 2030)
  • Suns receive: Grayson Allen, Keon Johnson, Nassir Little, Jusuf Nurkic

Blazers set to capitalize on Bucks' inevitable downfall

Looking at the state of the current Bucks roster, it's hard to believe they won a championship in 2021. They had poor asset management when breaking up their star trio, as they now have very little to show for moving Jrue Holiday and Khris Middleton.

To make matters worse, Milwaukee keeps digging itself a deeper hole, trying to remain competitive so that Giannis doesn't request a trade. They owe future draft capital to both Portland and New Orleans, and can't fully embrace a rebuild if Giannis eventually wants out.

That desperation has led them to make these myopic moves, such as trading for polarizing forward Kyle Kuzma or overpaying Myles Turner in free agency after an underwhelming Finals series. These were one step forward, two steps backwards types of move that only gets Milwaukee closer to purgatory rather than their ultimate goal of contention.

Giannis has to be aware of this roster issue, especially after the way they have played as of late without him. With injuries to stars such as Jayson Tatum and Tyrese Haliburton, this was a golden opportunity for the Bucks to regain their contender status in a weakened Eastern Conference. Instead, they now sit at 8-10, lacking the flexibility to upgrade their roster due to the lack of draft capital and overpaid contracts. And in order to sign Turner, they also decided to waive and stretch Lillard, owing him $22 million annually over the next five years!

Milwaukee reached a multiyear extension with general manager Jon Horst in April, which should only continue to work in Portland's favor. This Bucks roster is going nowhere fast, and Blazers fans should be feeling better than ever about the Lillard trade after seeing firsthand just how bad their situation truly is.

Whether it's upgrading their roster via the draft or packaging these valuable picks to land a star, Portland is in a prime position to capitalize on Milwaukee's downfall.

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