He knows about what it takes to win multiple titles in close proximity as one of the only players to have won multiple titles with 3 different teams.

For now, the Celtics also have a scoring punch in the backcourt from Anfernee Simons, who they acquired in the Holiday trade with Portland. However, many reports since Simons’ arrival have indicated that Boston might be parting with the guard before he ever plays a game with the franchise.

In a recent press conference, Celtics general manager Brad Stevens spoke about Anfernee Simons, who they acquired in the Holiday trade. In doing so, Stevens made it seem like Simons would be a big part of the team, even though he had already been named as a potential trade candidate.

The Achilles injury that could sideline Damian Lillard until the 2026-27 season didn't stop him from receiving "dozens" of offers following the Milwaukee Bucks' decision to waive him, according to ESPN's Shams Charania.

The Boston Celtics were among the top contenders for Damian Lillard. Discover the latest news on the Celtics and Lillard's future.

The University of Illinois alum started his career in the BAA/NBA with the (defunct) Chicago Stags, and also suited up for the (then) Philadelphia (now, Golden State) Warriors and (then) Fort Wayne (now, Detroit) Pistons before joining the Celtics for the last two seasons of his NBA career in 1956, helping Boston win their first title in 1957.