3 Offseason moves the Portland Trail Blazers might already regret

Robert Williams III (left), Malcolm Brogdon; Boston Celtics
Robert Williams III (left), Malcolm Brogdon; Boston Celtics / Brian Fluharty/GettyImages
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The Portland Trail Blazers just went through multiple years worth of roster turnover in just one offseason. Gone is franchise icon Damian Lillard and long-time center Jusuf Nurkic. Drew Eubanks, who played a key role behind the oft-injured Nurkic, is now with the Phoenix Suns, as is Nassir Little. Trendon Watford looked good in bursts as a small-ball center in 2022-23. Now, he's in Brooklyn.

In came No. 3 overall pick Scoot Henderson, who's slated to take over Lillard's role at point guard, despite his slow start and recent injury. Malcolm Brogdon and Robert Williams III arrived in Portland in part two of the Lillard trade via Boston, as general manager Joe Cronin flipped Jrue Holiday - who came from Milwaukee in the Dame deal - to the Celtics.

Deandre Ayton is now Rip City's franchise big man after essentially swapping places with Nurkic. Kris Murray was Portland's other first-round draft pick, a potentially ready-made three-and-D wing. Rayan Rupert was the team's second-round selection. Toumani Camara, also a second-round pick in the 2023 draft, came from Phoenix along with Ayton.

End-of-bench players Duop Reath, Moses Brown and Ish Wainright were added to the roster during the preseason.

Cronin brought back forward Jerami Grant on a five-year, $160 million contract and matched a three-year, $33 million Dallas Mavericks offer sheet for Matisse Thybulle.

Again - multiple years' worth of roster turnover in a matter of months.

Some of these moves have gone swimmingly. Camara, for example, appears to be a home run grab. Others, though, haven't gone according to plan.

If we could ask Cronin whether he'd take a mulligan on any of these transactions, which would he choose? How about these three?

1. Acquiring Robert Williams III in the Jrue Holiday trade

Robert Williams in theory is different than Robert Williams in practice. Mostly because, in practice, Robert Williams doesn't practice.

That's a semi-confusing way of saying Williams is an explosive shot-blocker and rim-runner and one of the best defensive big men in the NBA, but he's rarely healthy, and it didn't take long for him to hit the shelf in Portland.

The most games Rob Will has played in one season in the NBA were the 61 he started for the Celtics in 2021-22 when he was named Second-Team All-Defense. If he could come even close to that with the Blazers, it would be a massive win, especially considering his team-friendly contract that pays him less than $12 million annually.

Well, he played 119 total minutes for the Blazers across six games before hurting his knee and undergoing season-ending surgery.

Brogdon has been a key contributor this season when he's been healthy (he dealt with a hamstring injury and returned on Nov. 21). That part of the trade, along with the two future first-round picks Cronin acquired, have worked out. The Williams part, not so much. At the time of the deal, it seemed like Time Lord would be worth the risk. Hindsight is 20/20, but it turns out it was not.

The Blazers could have found other ways to match salaries in the trade, such as acquiring Al Horford and a minimum-salaried Celtic, or a group of them. It didn't play out that way, and Cronin has to be carrying at least some regret over the decision.