Portland Trail Blazers guard Damian Lillard (0) Stephen Lew-USA TODAY Sports

New trade makes Damian Lillard return look even better for Portland

The Portland Trail Blazers have flipped Damian Lillard into five first-round picks — and they're not done yet.

Days after acquiring Holiday in a three-team trade that sent Lillard to the Milwaukee Bucks, Portland dealt the two-time All-Star point guard to the Boston Celtics. After getting three Bucks first-round picks, along with former No. 1 pick Deandre Ayton, Portland added two more. Now Portland owns the Golden State Warriors' first-rounder next year plus Boston's unprotected first-round pick in 2029.

They might turn that into even more. While Portland could hold onto Williams, an occasionally dominant defensive center who has trouble staying healthy, Brogdon will likely take Holiday's place on the trade block. Portland already has young guards Scoot Henderson and Anfernee Simons in the backcourt, so Brogdon becomes another expendable veteran guard.

Portland likely won't do it any time soon, but one or both of their two recently acquired centers might also get traded, expanding the trade return even further. Not a bad haul for a 33-year-old guard who makes over $200 million in the next four seasons.

The Blazers have transformed from a team mired in mediocrity with an unhappy star to a team fully committed to a rebuild, well-stocked for future moves in one summer. They won't be a contender next year, but they haven't been a real contender since 2019. Now they're poised to find out what they have in their young players — and when those players are ready to contend, they've got plenty of assets to get them help.

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