While the Celtics were in the running to land Damian Lillard on the free agency market, instead, the nine-time All-Star chose to return to the Trail Blazers. Lillard reportedly agreed to a three-year contract with Portland, reuniting with his first NBA team.
When Lillard was traded to the Bucks two years ago, it was a huge deal that ended up benefiting the Celtics. As part of the deal, Jrue Holiday was moved to the Trail Blazers with the likelihood he would get re-routed to a contender. That’s exactly what happened as the Celtics swooped in to land Holiday. Of course, the rest is history as Holiday was a key part of the Celtics’ 2024 NBA championship run.
Now, two years after the Celtics-Blazers trade, both Holiday and Lillard are back in Portland. The Bucks stunningly stretched-then-waived Lillard’s contract, making him an unexpected free agent this summer. Lillard is coming off a ruptured Achilles tendon, but there was still interest in his services beyond just the 2025-26 season.
The Blazers originally traded Lillard to the Bucks for Holiday and other assets. The Celtics then sent Malcolm Brogdon, Robert Williams III and two first-round picks to the Blazers to land Holiday. In an interesting twist, the Blazers now have Lillard (free agency), Holiday (trade) and Williams still on their roster.
Portland is in an interesting spot as it largely flied under the radar last season. The Blazers started slow with a 13-28 record, but they finished the season 23-18. There was a defensive identity being built in Portland as it has plenty of young guards in Shaedon Sharpe and Scoot Henderson. Now, they have veterans like Holiday and Lillard, though the latter won’t play much, if at all, this upcoming season.
Regardless, the Blazers are in a transition phase after their big Lillard trade two years ago. They’ve stockpiled some talent and 16th-overall pick Yang Hansen has drawn some attention throughout Summer League. The Blazers are looking like they’re building something in Portland after rebuilding in recent seasons.
On the Celtics’ end, they got what they needed over the past couple seasons. Holiday was crucial in the 2024 title run, bringing some championship pedigree. They were then able to flip Holiday back to the Blazers in exchange for Anfernee Simons, saving a significant amount of short- and long-term money in the process. So, it appears it worked out for both sides in the Celtics and Blazers.
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