The Bucks traded Holiday to the Blazers for Lillard in a blockbuster deal in September. Holiday was then traded by the Blazers to the Celtics on October 1.

Holiday spent three seasons on the Bucks. He averaged 18.5 points, 4.7 rebounds, 6.8 assists, 1.5 steals and 0.5 blocks and helped the franchise win the 2021 championship over the Phoenix Suns in six games.

Blazers head coach Chauncey Billups helped Holiday process the Bucks trade. Holiday and Billups spoke to NBA reporter Jared Weiss of The Athletic about their conversation after the Bucks traded Holiday to the Blazers.

“It meant a lot,” Holiday told The Athletic. “Being able to see a coach that has my best interests (in mind). And you could see it and you could hear it, which a lot of times maybe some players don’t get a chance to see that from a coach. So he definitely had my best interest (at heart) from the beginning. And he just always looked out for me.”

Billups and Holiday had a great conversation during the time Holiday was officially a member of the Blazers, who are in rebuild mode in the post-Lillard era.

“I had a great conversation with him,” Billups said. “I did. I love Jrue, man. I love Jrue. And we got him very briefly obviously. And I had a conversation — a long, good conversation with him — just about I know it was a little tough spot for him, being traded, kind of being blindsided by that. I’ve been there before. So just being able to rap with him like that because I know him. And it was important for me that a good person like him, who’s been great on every team and every community that he’s lived in, for him to be treated properly and be put in a great position and a great spot.”

Holiday is averaging 12.8 points, 5.4 rebounds, 4.9 assists, 0.9 steals and 0.8 blocks this season for the Celtics, who have the best record in the NBA.