The Boston Celtics dumped Jrue Holiday on the Trail Blazers this offseason as they looked to dodge spending concerns, but the move was quickly made redundant in Portland. Holiday was supposed to be a veteran leader and mentor for their young talent. He will be, but the Blazers couldn’t pass up adding Damian Lillard after the Bucks sent him packing. Now, Portland has two veteran guards, and the franchise legend will quickly become the trusted voice in the locker room.
The Celtics have their own problems after this trade. They want to dump Anfernee Simons to get under the luxury tax, but that has proven impossible. Boston will take the 26-year-old guard into the season and hopes to showcase him enough to find a taker for his expiring contract.
Holiday won a championship and played a key role for the Celtics. He clearly still bleeds green, but is now Portland’s highest-paid player. The 6’4 guard is under contract through 2028. Do not be surprised to hear the Blazers are shopping him soon, especially when Lillard is ready to return from his Achilles surgery.
Celtics got the last laugh as Jrue Holiday instantly became redundant in Portland
The Blazers showed promise to close last season and were eager to add a veteran with winning experience. Boston wanted to move off of Holiday’s contract. This swap made perfect sense in the moment, but quickly turned into a head-scratcher for both sides. The Celtics can’t dump Simons, and the Trail Blazers now have two veteran guards with two young building blocks hoping to breakout into larger roles.
The Blazers won’t have issues this season. There will be plenty of minutes for Scoot Henderson and Shaedon Sharpe next to Holiday, but that changes when Dame returns. Both veterans will want significant run. Unless the Blazers plan to use exclusively three-guard looks, the squeeze will come somewhere.
Portland doesn’t need Holiday after signing Damian Lillard. The franchise legend wants to end his career with the Blazers. He will be a fantastic mentor for their young guards and likely leads his longtime franchise into the next generation.
Jrue Holiday is declining. Celtics fans saw that firsthand. He is best in a leadership role where he can play 25 to 30 minutes per game. Holiday can still make an impact on both ends of the floor, but the 35-year-old needs more rest. This leaves the Blazers with a future problem and plenty of questions. That is not where they expected to be after making this trade.
The Boston Celtics have no regrets. They saved significant money and have the shot to get value from Anfernee Simons before the deadline. This could be a fantastic move, and it is only made better by the Blazers' instant regret. Brad Stevens certainly did it again, which should be no surprise.