Jrue Holiday Trade Looks Better by the Day for the Blazers After Celtics Flip Simons for Vučević
When the Portland Trail Blazers traded Anfernee Simons to the Boston Celtics in exchange for Jrue Holiday over the summer, it raised more than a few eyebrows. At first glance, it looked like a team in the middle of a rebuild was opting for a 35-year-old veteran over a 26-year-old scorer still entering his prime. But fast forward to now, and that move is aging like fine wine for the Blazers’ front office.
On Tuesday, the Celtics moved Simons again-this time to the Chicago Bulls, along with a second-round pick, in exchange for center Nikola Vučević. And just like that, the value of Portland’s original trade with Boston is starting to shine a little brighter.
Let’s be clear: Vučević and Holiday are completely different players, filling vastly different roles. But when you look at overall impact, there’s no question which player is offering more right now.
Holiday continues to be a high-level contributor on both ends of the floor, while Vučević, for all his offensive skill, remains a defensive liability. It’s a swing by Boston that may help their frontcourt depth and cap sheet, but it also underscores just how much more Portland got back in their original deal.
Holiday’s Value Has Only Grown
At the time of the trade, one of the biggest knocks on Portland’s decision was the contract situation. Holiday is under contract through the 2027-28 season, with a $37.2 million player option that he’s unlikely to turn down.
Simons, on the other hand, is on an expiring deal. The optics weren’t great: a rebuilding team taking on long-term money for an aging guard.
But Holiday has flipped that narrative on its head with his play this season.
He’s averaging 14.3 points per game-his highest scoring output since his early days in Milwaukee-along with 4.5 rebounds, 6.7 assists, and 1.3 steals. He’s shooting 43% from the field and hitting 35.3% of his threes on over six attempts per game. Those aren’t just solid numbers-they’re proof that Holiday still has plenty left in the tank, even in his 17th NBA season.
He’s brought stability, leadership, and two-way play to a young Blazers team that’s still figuring itself out. And if Portland does decide to move him down the line-whether at the trade deadline or in the offseason-they’re likely to get more in return than Boston just got for Simons.
Celtics’ Cap Play Opens the Door
For Boston, this latest deal was as much about the books as it was about basketball. By trading Simons and bringing in Vučević, the Celtics move below the first tax apron-a key financial threshold that affects roster flexibility. It’s a continuation of the same cost-cutting strategy that made Holiday available to Portland in the first place.
Vučević, on an expiring contract, could be a short-term rental for Boston. Simons is also on an expiring deal, which made him a movable piece for the Celtics. But the fact that Boston attached a second-round pick just to make the swap suggests they weren’t sold on Simons as a long-term fit.
That’s a stark contrast to how Portland has used Holiday-leaning on him as a veteran presence and letting him run the show when needed.
Could a Bigger Deal Be on the Horizon?
As of now, there’s no indication that Portland is actively shopping Holiday. But that doesn’t mean his name won’t surface in trade talks.
The Knicks have reportedly shown interest, and the Blazers have long admired Mikal Bridges. If those two teams ever find common ground, it could be the kind of move that further validates Portland’s decision to bring in Holiday in the first place.
For now, though, the Blazers have a proven winner in their locker room, and they’re in no rush to move him. Holiday’s performance has already silenced much of the early criticism around the trade. And if a bigger opportunity comes along, GM Joe Cronin could end up looking even more shrewd than he already does.
In a league that moves fast and rarely waits for long-term context, the Holiday-for-Simons deal is starting to look like a win for Portland-not just in theory, but in practice.