Former Celtics Guard is a Big Reason Damian Lillard Chose Blazers Over Boston

The Boston Celtics initially acquired All-Star guard Jrue Holiday in a trade with the Portland Trail Blazers in September 2023.

The Trail Blazers had just received Holiday in a trade that sent superstar Damian Lillard to the Milwaukee Bucks before sending Holiday to Boston. In exchange, Portland received Malcolm Brogdon, Robert Williams, a 2024 first-round draft pick and a 2029 unprotected first-round draft pick.

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Now, two seasons later, the Celtics have traded Holiday back to the Trail Blazers for guard Anfernee Simons. And this deal would end up getting Portland a second superstar they had parted ways with in the past.

Holiday reportedly influenced Lillard’s decision to re-sign with the Trail Blazers. The Bucks, who acquired Lillard from the Trail Blazers in 2023, waived the eight-time NBA All-Star to clear cap space for former Indiana Pacers center Myles Turner.

Lillard is set to sign a three-year contract with his former team and join forces with Holiday for the first time in the NBA.

“As soon as I was waived and obviously [Jrue] knows that I live here and built my home here and stuff,” Lillard told reporters in Portland. “He sent me the eyeball emoji. I kind of knew already like — I already knew where I was pivoting to when he sent it but I didn’t want to say nothing too soon, so here we are.”

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Lillard had already spent the first eight seasons of his career with the Trail Blazers and purchased a home in Portland. And so, when the Bucks waived him, it gave Lillard the chance to return to his original team.

Holiday and Lillard have never played on the same NBA team, despite being involved in the same three-team trade deal in 2023. The pair won an Olympic gold medal together for Team USA at the 2020 Tokyo Olympics.

Lillard is expected to miss all of next season recovering from a torn Achilles tendon he sustained during the playoffs. There have been rumors that Holiday could be traded before Lillard returns.

But if Holiday is still on the team when Lillard comes back, the duo play together in the NBA for the first time.

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