Damian Lillard 'Really Considered' Signing With Celtics Before Blazers Deal

The Boston Celtics tried signing Damian Lillard during free agency, but he ended up choosing to return home with the Portland Trail Blazers.

The Celtics were in the hunt for Lillard's signature after he got waived from the Milwaukee Bucks. Reports indicate that the guard was getting recruited by Jayson Tatum.

The Celtics faced several obstacles in getting Lillard's signature. His family is based in the west coast and he reportedly didn't enjoy his time living in Milwaukee.

Boston also could only offer a taxpayer mid-level exception, which is much less than a team like the Blazers could offer.

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Despite the hurdles, they were in the race, according to ESPN's Shams Charania.

"Over a dozen teams made minimum and midlevel exception offers to Dame," he said on an ESPN broadcast.

"Two teams, in particular, I'm told that Damian Lillard really considered: Celtics and the Timberwolves. He held calls with both teams at different points."

Shams: "Over a dozen teams made minimum and midlevel exception offers to Dame. Two teams in particular I'm told that Damian Lillard really considered: Celtics and the Timberwolves. He held calls with both teams at different points" pic.twitter.com/I8HmWzF8wm
— Oh No He Didn't (@ohnohedidnt24) July 18, 2025

Lillard tore his Achilles during the NBA playoffs, which means he will not play during the upcoming season, making the first year of any contract he signs moot.

He will spend the entire season rehabilitating and potentially return at the start of the 2026-27 season.

Additionally, the injury could alter his on-court abilities, especially as an undersized guard. He relies on explosiveness and his ball-handling to attack a defense and open up the court for his lethal 3-point shooting.

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Most athletes lose a good chunk of athleticism after an Achilles injury. Lillard might never reach his All-Star level again.

While he presented a good low-risk, high-reward proposition, he would not have changed the calculus for the upcoming season for the Celtics.

Also, the team is trying to cut down on payroll, and adding another star player could further restrict the team as well.

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