Some sections of Boston's fan base may view this as a missed opportunity. Yet, it's vital to put things into perspective.

Portland also bought out starting center Deandre Ayton, who signed with the Los Angeles Lakers as a free agent. The Trail Blazers still boast two movable veteran contracts in the deals of forward Jerami Grant and center Robert Williams, and could theoretically add younger players who better align with the club's timeline.

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The Boston Celtics and Minnesota Timberwolves offered contracts to Damian Lillard, according to Shams Charania of ESPN. However, Lillard chose to sign a three-year, $42 million contract with the Portland Trail Blazers.

From Lillard’s perspective, joining the Celtics could give him a realistic shot at a title in 2027, depending on how Tatum recovers and how Stevens and Co. piece together the rest of the roster. The 13-year veteran’s deepest playoff run was a trip to the Western Conference finals with Portland in 2019.

To that end, a new update has been revealed about Boston's rumored pursuit of Lillard. According to Gary Washburn of the Boston Globe, Tatum has been actively recruiting Lillard to the Celtics.

Tatum is looking to convince Damian Lillard to join the Celtics after he was waived by the Milwaukee Bucks, according to the Boston Globe. Both players tore their Achilles during the NBA playoffs and will miss most, if not all, of the 2025-26 season.

New York Knicks guard Josh Hart disclosed his reaction to the Milwaukee Bucks waiving and extending the contract of star point guard Damian Lillard.