Let’s Talk About Jrue Holiday’s New Zip Code
In another head-turning NBA twist, veteran guard Jrue Holiday is officially heading west — again. The Portland Trail Blazers have struck a deal with the Boston Celtics to acquire the defensive powerhouse. And while Holiday’s been no stranger to shipping labels lately, this move brings him to a team that’s clearly trying to fast-track a retooling process.
Sources including ESPN, The Athletic, and the Boston Globe all confirmed Monday night that the Blazers are trading away Anfernee Simons and two second-round picks in exchange for the two-time NBA champ. This trade adds another layer of intrigue to an already spicy NBA offseason.
The Swap: Simons Out, Holiday In
Here’s what the trade looks like on paper:
🔁 To Boston Celtics:
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Anfernee Simons
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Two second-round draft picks
🔁 To Portland Trail Blazers:
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Jrue Holiday
At first glance, it’s a trade that meets both teams' needs: Boston gets younger and adds scoring depth in Simons, while Portland gets a proven leader and elite defender who’s battle-tested and still has gas in the tank — even at 35.
Holiday’s Hoops Resume: A Closer Look
Jrue Holiday might be entering his mid-thirties, but don’t let that number fool you — his career has been one of consistent high-level play and lockdown defense.
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🏆 2× NBA Champion
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🌟 2× NBA All-Star
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🛡️ 6× NBA All-Defensive Team
Though his numbers dipped last season — 11.1 points, 4.3 rebounds, and 3.9 assists over 62 starts — he’s never been the type to chase stat sheets. Holiday’s real value lies in his leadership, grit, and ability to shut down the opposing team’s top guard. His scoring average last season was his lowest since his rookie year in 2009-10, but his experience and two-way reliability still make him a coveted asset.
And let’s not forget: in 2024, Holiday inked a four-year, $135 million contract extension with Boston. That means he’s on the books for $32.4 million in 2025-26, $34.8 million in 2026-27, and he holds a $37.2 million player option for the 2027-28 season.
Wait, Didn’t the Blazers Just Have Holiday?
Funny you should ask. Yes, Portland already had Jrue Holiday — for about five minutes.
Back in 2023, Holiday was part of the massive trade that sent Damian Lillard to the Milwaukee Bucks. As part of that three-team blockbuster, the Bucks sent Holiday to Portland… only for him to be rerouted to Boston days later. It was a pit stop in name only.
Now, the Blazers are finally cashing in on his presence — this time, for real.
Simons’ Journey and What He Brings to Boston
On the flip side, Boston is gaining one of the league’s most underrated offensive threats in Anfernee Simons. The 26-year-old was the No. 24 pick in the 2018 NBA Draft and has gradually blossomed into a versatile scorer and secondary playmaker.
Last season, Simons averaged:
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📊 19.3 points
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🎯 4.8 assists
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🏀 2.7 rebounds
...over a career-high 70 starts.
His best work arguably came during the 2023-24 season when he averaged 22.6 points, 5.5 assists, and 3.6 rebounds across 46 starts. That's a solid step up and a clear sign of a player trending upward.
Simons also signed a hefty four-year, $100 million deal with the Blazers back in 2022. He's on the books for $27.6 million in 2025-26 — the final year of that contract. The Celtics now add a young, talented guard who could be a long-term piece or a high-value trade chip later on.
What This Means for the Blazers
For Portland, this move screams “veteran leadership.”
They’re a team in transition, looking to surround their young core — including Scoot Henderson and Shaedon Sharpe — with established voices and defenders who know how to win. Jrue brings not just championship DNA but also the kind of hard-nosed presence that can help groom a young squad.
🟢 Perks for Portland:
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A battle-tested playoff veteran
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An elite perimeter defender
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Instant credibility in the locker room
Though Holiday isn’t the long-term future of the team, his impact in the next few seasons could be huge in shaping the identity of the new-look Blazers.
What This Means for the Celtics
Boston, fresh off a strong postseason showing, just made a move that might look risky but could pay off big. Losing Holiday’s defense stings, no doubt. But adding Simons gives the Celtics more offensive punch and flexibility — especially if they're looking to retool around Jayson Tatum and Jaylen Brown without busting the budget.
🟣 Perks for Boston:
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Younger, cheaper scoring option
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More room to maneuver financially
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A player still entering his prime
Simons may not replace Holiday's defensive chops, but paired with Boston’s existing defensive structure, he could thrive in a sixth-man role or even as a complementary starter.
Looking Ahead
This trade isn’t just about numbers. It’s about identity. Portland gets a seasoned floor general who brings stability and toughness. Boston gets a young, dynamic scorer with upside. Both teams are looking to balance the now and the future, and this move helps them inch closer to that goal.
Let’s see how it all unfolds — because in the NBA, nothing ever stays still for long. And this deal? It might just be the start of another ripple effect across the league.
Key Takeaways:
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✅ Jrue Holiday lands in Portland after being traded (again), this time for Anfernee Simons and two second-round picks.
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🔥 Holiday’s defensive legacy and playoff experience add instant value to the Blazers’ young roster.
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📈 Simons gives Boston a scoring boost and potential long-term guard depth as they chase banner No. 18.
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💸 Both players are locked into high-value contracts, making this trade a major financial and strategic chess move.
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