Dec 23, 2023; New York, New York, USA; Milwaukee Bucks guard Damian Lillard (0) reacts after a non-call in the fourth quarter against the New York Knicks at Madison Square Garden. Mandatory Credit: Wendell Cruz-Imagn Images Wendell Cruz-Imagn Images

Blazers GM Didn't Like Damian Lillard With Bucks

Originally posted on Milwaukee Bucks on SI
By Ryan Stano | Last updated Jul 22, 2025 4:30 PM ET

The Milwaukee Bucks were not expected to end the Damian Lillard era this offseason. They certainly weren't expected to use the stretch-and-waive provision on him, which is what they ended up doing.

Lillard will miss all of next season due to a torn Achilles that he suffered in the first round of the playoffs against the Indiana Pacers. He won't be playing for the Bucks, though.

Lillard decided to re-sign with the Portland Trail Blazers, signing a three-year deal worth $42 million. His new general manager didn't like seeing him play for Milwaukee in the last two seasons.

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Joe Cronin, the general manager in Portland, didn't like seeing Lillard play for another team. He very much wanted to bring Lillard back home.

Joe Cronin: "It never felt right seeing Damian in a different jersey. We're really excited to bring him back to Portland."
— Sean Highkin (@highkin) July 22, 2025

Portland only traded Lillard because Lillard wanted a chance to chase a ring with another team. Portland would have been happy to keep Lillard forever.

Milwaukee was eliminated in the first round of the playoffs in each of Lillard's two seasons, so it's impossible to claim that the trade was a success. They also now have $22.5 million on their books for the next five seasons because of him.

Trading for Lillard was a big swing that the Bucks made, but it ended up not working out. It's a decision that could end up pushing Giannis Antetokounmpo out of Milwaukee if they aren't careful.

With Lillard gone, the Bucks don't have a point guard that they truly trust on the roster. Kevin Porter Jr. will start next season, but he is clearly a more effective bench player than he is as a starter.

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Milwaukee looked good on offense when Lillard and Antetokounmpo were both healthy, but they weren't healthy enough together when it really mattered the most.

It ended up being the wrong move to trade Jrue Holiday for Lillard, but fans shouldn't be upset that the Bucks took a big swing. Taking big swings can win teams championships, as they saw firsthand when they traded for Holiday in the first place.

This past season with the Bucks, Lillard averaged 24.9 points, 4.7 rebounds, and 7.1 assists per game.

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This article first appeared on Milwaukee Bucks on SI and was syndicated with permission.

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