Damian Lillard to Bucks; Blazers Get Jrue Holiday, Deandre Ayton in 3-Team Trade

The Damian Lillard era in Portland is over.

The Trail Blazers agreed to trade their future Hall of Fame guard to the Milwaukee Bucks in a three-team trade also involving the Phoenix Suns, the Blazers announced on Wednesday night.

ESPN's Adrian Wojnarowski first reported the news and shared the full details of the blockbuster:

Lillard spent his first 11 seasons in Portland, becoming a franchise icon who eschewed greener championship pastures to attempt to make things work.

It never did.

The Blazers made a surprising run to the Western Conference Finals in 2019 but were otherwise a playoff also-ran. Portland was swept or lost in five games in four different first-round playoff series. The team concluded the Lillard era with back-to-back lottery seasons.

Despite near-constant speculation that Lillard would request a trade, he consistently said he was willing to "die" on the hill of staying in Portland his whole career.

"To give that experience to people on a consistent basis for years and years and years, I look out there and I see my jersey everywhere," Lillard told ESPN's Baxter Holmes. "The love hasn't faded. [Not like], 'Oh, we loved Dame for his first six years.' Like, I'm seeing my jersey out there consistently and it's been over a decade. Other than a championship, what more can I give?"

Major changes happened this summer, as the Blazers won the No. 3 pick in the lottery. While Portland explored the potential of trading that selection for a veteran star who could play next to Lillard, no deal materialized and the Blazers selected Scoot Henderson—an obvious long-term Lillard replacement.

Lillard met with Blazers brass ahead of the start of the 2023 free-agency period, giving the team one final opportunity to improve the team and show a commitment to winning. When Portland failed to make a major splash in the early hours of free agency, Lillard informed the Blazers he wanted a trade.

"We have been clear that we want Dame here but he notified us today he wants out and he'd prefer to play someplace else," Portland general manager Joe Cronin said in a statement on July 1. "What has not changed for us is that we're committed to winning, and we are going to do what's best for the team in pursuit of that goal."

Lillard told the Blazers he preferred a trade to Miami, but Cronin was adamant the team would do what was in its best interest. In the end, Portland shipped Lillard to Milwaukee.

As it stands, the Bucks view Lillard as a cornerstone piece to their championship push. The All-Star joins Giannis Antetokounmpo as pillars of the franchise, creating a team that should be on the shortlist of title favorites. The deal comes weeks after Antetokounmpo, who's eligible for free agency in 2025, offered some cryptic comments about his long-term future in Milwaukee.

After years of pushing back against it, Lillard will finally get to see if the grass is indeed greener on the other side. Whether that proves true could carry major consequences for the Bucks.