Portland Trail Blazers general manager Joe Cronin has had a few significant trade wins in the past few years for which he deserves credit. He landed building block wings in Deni Avdija and Toumani Camara, and Portland is well-positioned for years to come thanks to their Damian Lillard deal with the Milwaukee Bucks. But there have also been some head-scratching trades in the mix, including both Jrue Holiday deals with the Boston Celtics.
Revisiting Jrue Holiday trade No. 1
Trail Blazers received: Robert Williams III, Malcolm Brogdon, 2024 first-round pick (via Golden State), 2029 first-round pick
Celtics received: Jrue Holiday
Robert Williams III was a key piece in this deal for the Blazers. Unfortunately, his injury problems weren't magically solved by coming over to Portland. In fact, they have gotten worse. Williams has been impactful for the Blazers when he's been on the court these past two seasons. The issue, however, is that those moments have been few and far between, as he's played a total of just 26 games during that stretch.
Portland did manage to turn the other pieces into Deni Avdija in their deal with the Wizards (with the 2029 pick heading to Washington being the second-most favorable between Portland, Boston, and Milwaukee). From that standpoint, this deal doesn't look quite as bad. But that had more to do with the Blazers stealing Avdija from the rebuilding Wizards.
In terms of grading individual trades, this was a clear fleece for Boston. Holiday was Boston's missing piece to help Jayson Tatum, Jaylen Brown, and company get over the top, resulting in a ring in 2024.
Meanwhile, Portland got an unreliable player in Williams, a veteran guard who didn't fit their timeline in Brogdon, a No. 14 overall pick in a weak draft class, and a future first-round pick for a franchise that will still be competitive at that point. The Celtics will still be good in 2029, partly because of their pivotal offseason. Thanks to Portland taking on Holiday's contract and the Atlanta Hawks taking on Kristaps Porzingis, Boston got under the second apron.
Revisiting Jrue Holiday trade No. 2
Trail Blazers received: Jrue Holiday
Celtics received: Anfernee Simons
Initially, Portland was set to include second-round picks in this trade, making it even more lopsided. That ultimately was revised to a straight one-for-one swap of Holiday for Anfernee Simons due to Portland's slight concerns surrounding Holiday's medicals. Great.
Even assuming Holiday remains healthy, this is another loss for Portland. Holiday will be a valuable mentor for Portland's young core, and his versatility shouldn't interfere with their development too much. But he's also 35 years old and coming off a season where he averaged 11.1 points and 3.9 assists.
Portland's timing of trading away and reacquiring Holiday couldn't have been worse. Boston needed one more piece to win a championship, and Portland gave it to them at a relative discount. Boston needed to get off said guard's three-year, $104 million contract, and Portland took him back for a skilled Simons on an expiring deal.
Besides their buy-low flier on Dalano Banton, the Blazers' recent trades with the Celtics have been disastrous for the long-term outlook. At this point, Portland needs to stop making deals with Boston.