Well, well, well. Jrue Holiday is on the move again, and this time, the ripple effects might just circle all the way back to New Orleans. The Boston Celtics just offloaded Holiday to the Portland Trail Blazers, and while the headlines have mostly focused on Boston’s salary cap gymnastics (and rightly so), there’s an unexpected subplot brewing—one that involves Zion Williamson, some wishful thinking, and maybe a little deja vu from Pelicans fans.

Let’s break this whole Jrue Holiday saga down and dig into why his name is suddenly popping up in connection to the Pelicans—again.

The Celtics’ first major offseason domino just fell, and it’s a big one: Jrue Holiday, the defensive heartbeat of their 2024 championship run, was shipped to Portland for Anfernee Simons and two second-round picks. On paper, this looks like a fair swap—until you peek behind the curtain and see the real reason Brad Stevens made the move.

This wasn’t about talent. It was about taxes. Boston was staring down a $500 million payroll iceberg, and Jrue’s escalating contract—$104.4 million over three years, including a $37.2M player option in 2027-28—was the heaviest anchor on the ship. By trading him, they cleared out $40 million in projected tax penalties and gave themselves enough breathing room under the second apron to avoid having to pay Adam Silver’s kids’ college tuition directly.

It’s a cold business move, but Stevens made it with the precision of Tim Duncan backing down a switch mismatch—clinical, quiet, and effective.

Incoming guard Anfernee Simons is no slouch—he’s younger, cheaper, and he averaged 19.3 points per game last season while doing his best impression of CJ McCollum in a G League jersey. He arrives on an expiring $27.7 million deal, which means he could be either a stopgap or a sweetener for Boston’s next trade. That’s right: this might just be the warm-up act.

According to Shams Charania, the Celtics are still working the phones like it’s trade deadline week. Kristaps Porzingis? Reportedly on the block. Sam Hauser? Possibly packing. Even Derrick White’s name has floated into the rumor waters. With Jayson Tatum recovering from an Achilles injury, Boston is entering what insiders are calling a “bridge year” and it might look more like a full-on roster remodel.

Think of it like a Dynasty reboot—same core, new supporting cast, slightly less elegant drama.

So, where do the Pelicans come into this?

Ah, yes, the surprise twist in the Jrue Holiday story—the Pelicans link. According to Ryen Russillo, there’s still affection from the Pelicans’ ownership toward Zion Williamson, despite the never-ending injury roulette and the fact that the only thing more consistent than Zion’s DNPs is his preseason hype.

Russillo says ownership remains committed to Zion, but he personally thinks it might be time to move on: “Even though I think all of us, when it’s good, we love watching it… But there’s also a basketball question with Zion, because the best version of him is when he’s your point guard and you just let him go Point Zion—and he k—-s everybody.”

Translation: Zion is still electrifying when healthy, but asking him to be the offensive engine is like building your offense around a weather report—you’ll only know if it works 10 minutes before the game starts.

That’s where Jrue Holiday comes in—again. If Portland decides they don’t need a veteran guard with a championship resume and a $104M price tag on a rebuilding roster, could a trade back to New Orleans make sense? A reunion with Brandon Ingram (for however long he’s still there), and a stabilizing voice next to Zion? It’s not as far-fetched as it sounds. Especially considering that the Pelicans’ leadership still values the narrative, one where their star doesn’t force his way out and they build a real, cohesive team.

Let’s be honest: Jrue Holiday back in NOLA feels oddly poetic. He left as the last shred of structure before the Zion era began, and now he might just be the veteran glue it needs.

The Trail Blazers, to their credit, say they’re keeping Holiday. Head coach Chauncey Billups and Holiday have reportedly had a great relationship ever since that brief post-Dame-trade window in 2023 when Holiday was technically a Blazer for five minutes. This time, they might actually play him.

The idea is clear: if Scoot Henderson isn’t ready to lead just yet, Holiday can serve as a floor general, mentor, and defensive anchor. But paying $30M+ per season to a guy who might be a temporary fit while Scoot learns how to dribble without tripping feels… generous.

Then again, Portland has made bolder decisions. Like offering up max money to Evan Turner back in the day. (Yes, we remember. We all do.)

Let’s just take a moment to appreciate what Jrue Holiday represents. The guy wins. He plays elite defense. He passes, screens, and sacrifices. He’s basically the NBA’s answer to that one guy at work who does everything, never complains, and still brings cupcakes on his birthday.

This trade was no indictment of his value. It was a harsh reminder that in the modern NBA, value is measured in millions, not morals. Still, don’t be shocked if he ends up back in a playoff contender’s jersey by the trade deadline—or even in New Orleans, where this whole journey once kicked off.

Because Jrue Holiday might not be flashy. But in a league full of volatility, he’s that rare constant. And someone, somewhere—maybe even Zion and the Pelicans—could use exactly that.