Over the past few months, the Boston Celtics have made some significant changes, and they narrowly missed on a big free agent signing.
Since losing to the New York Knicks in the second round, Brad Stevens and the Celtics front office have been on a mission. Not only did the Celtics need to make some big moves to aid their financial situation, but they also needed to get into a position to contend for a title again when Jayson Tatum returns in 2026-27.
The biggest moves Boston made featured the Celtics sending out Jrue Holiday and Kristaps Porzingis. While those deals made plenty of sense for Boston from a financial perspective, one of those deals could have hurt the Celtics’ chances of landing a premier free agent.
After the Milwaukee Bucks waived and stretched Damian Lillard, the Celtics were among the few teams with a legitimate chance to add the nine-time All-Star. However, with Holiday now in Portland, his efforts to bring Lillard back to his first NBA franchise might have played a role in Boston’s miss.
“As soon as I got waived, he sent me the?emoji”
Dame says Jrue texted him recruiting him to Portland and asked to wear #0 ??
(Via @trailblazers) pic.twitter.com/WFjm3xOZUB
— Bleacher Report (@BleacherReport) July 24, 2025
Lillard recently explained that immediately after he was waived, Holiday sent him the eyeball emoji, looking to team up with the star guard in Portland. Eventually, Lillard landed back with the Trail Blazers on a three-year deal.
While Holiday’s texts and preexisting relationship with Lillard certainly could have made the decision easier, Lillard also noted that he already had an idea of where he wanted to go after his Bucks exit. Although it seems like Lillard was likely headed to his first franchise again anyway, it’s hard to believe that Holiday didn’t play at least some part in the relatively quick decision.
