The Boston Celtics and Chicago Bulls just pulled off a trade that could have ripple effects across both conferences. Boston is sending Anfernee Simons and a second-round pick to Chicago in exchange for veteran big man Nikola Vucevic and a second-rounder of their own. It’s a move that says a lot about where the Celtics are headed this season-and how the Portland Trail Blazers’ earlier gamble on Jrue Holiday is aging like fine wine.
Let’s rewind for a second. This all started when Portland sent Simons to Boston in a one-for-one deal for Holiday over the summer.
At the time, it raised some eyebrows. Simons, younger and flashier, seemed like a building block.
But fast forward to now, and it’s clear Portland made that move at exactly the right time.
Holiday’s Resurgence in Portland
At 35, Jrue Holiday isn’t the high-flying athlete he once was, but he’s proving that savvy, skill, and leadership still matter in this league. Taking on an expanded role in Portland, Holiday has been quietly excellent-averaging 14.3 points, 6.7 assists, and 4.5 rebounds while shooting 43% from the field, 35% from deep, and 76% at the line. Those numbers don’t scream All-Star, but they do scream value, especially when you consider the context: a veteran stabilizing a young, rebuilding roster while also boosting his own trade stock.
And that stock is rising. Teams like the Knicks have already made calls, and with the trade deadline approaching, Portland is in a strong position to flip Holiday for more than what Boston just got in return for Simons. That’s the kind of asset management that can accelerate a rebuild.
Boston’s Perspective: Win-Now Mode
On the flip side, Boston’s move for Vucevic is a clear win-now play. The Celtics are betting on the idea that Jayson Tatum will be back and ready to lead a deep playoff push. Vucevic gives them a proven starting center who can stretch the floor, rebound, and provide some interior scoring-something they’ve lacked at times during their recent postseason runs.
But this isn’t just about basketball. It’s also about the books.
Vucevic is on an expiring deal and makes about $6 million less than Simons this season. That difference helps Boston duck the second tax apron, a cap management hurdle that’s become increasingly important under the league’s new collective bargaining agreement.
So while they may have sold low on Simons, they’re also giving themselves some breathing room financially.
Portland’s Long Game
Back in Portland, the Holiday acquisition continues to look smarter by the day. Not only has he played well, but his presence opens doors that Simons never could.
Take Mikal Bridges, for example-a player who’s been on the Blazers’ radar. Holiday’s value and veteran pedigree make deals like that at least worth a phone call.
Yes, there’s a long-term question here. Holiday is owed $37 million in the final year of his deal-when he’ll be 37 years old.
That’s a number that could become a headache. But the Blazers don’t have to wait for that to become a problem.
With interest already bubbling and Holiday’s connections around the league (including with Giannis Antetokounmpo), Portland can move now and avoid the future cap crunch altogether.
Bottom line: If the Blazers decide to move Holiday before the deadline, they’re likely to get a significantly better return than Boston just got for Simons. That’s the kind of value play that can shift a franchise’s trajectory-and it all started with a summer trade that didn’t get nearly enough attention at the time.
As for Boston, this is a calculated risk. Vucevic helps now, and the Celtics are clearly all-in on this season. But make no mistake-Portland’s the team that’s holding the better hand if they play their next move right.