Trail Blazers-Celtics Blockbuster Reimagined: Jrue Holiday for Anfernee Simons Swap Shakes NBA Landscape
In an alternate twist to the high-stakes NBA chessboard, the trade that once sent Jrue Holiday to the Boston Celtics takes a dramatic turn. Instead of the actual deal that saw the veteran guard head east in exchange for a package centered around Malcolm Brogdon and Robert Williams III, the Portland Trail Blazers opt for a different path: they strike a direct swap, sending emerging star Anfernee Simons to Boston in exchange for Holiday.
This version of the deal flips the trajectory of both franchises — one aiming for title contention, the other squarely in the middle of a rebuild — and raises compelling questions about value, fit, and long-term vision.
The Celtics, still in their championship window, know that youth doesn’t always equal readiness. But in this scenario, they decide to bet on upside and longevity, prioritizing Simons’ offensive dynamism over Holiday’s elite defense and veteran leadership.
Simons, who averaged 21.1 points and 4.1 assists during the 2022–23 season and improved as a playmaker in 2023–24, gives Boston a sharpshooting, three-level scorer who can slot in alongside Jayson Tatum and Jaylen Brown for years to come. While questions about defense arise immediately, Celtics President Brad Stevens clearly sees a long-term core of Tatum, Brown, and Simons as capable of maturing into a modern offensive juggernaut.
This deal also gives Boston some cap flexibility and age stability. Simons is locked into a reasonable contract through 2026, whereas Holiday, though still elite, is older and seeking a long-term extension worth significant money. Boston takes the gamble that in Simons, they’ve landed a future All-Star.
Portland’s Rationale: Leadership and Culture Over Stats
For the Trail Blazers, the reasoning is more emotional than statistical — and deeply strategic.
Jrue Holiday isn’t a player who fits the usual rebuilding mold. He’s a proven winner, a defensive maestro, and one of the most respected voices in any locker room. Portland’s GM, in this alternate timeline, views Holiday as more than just a stopgap. They see him as the veteran leader who can shepherd Scoot Henderson and Shaedon Sharpe into the future.
Holiday’s playoff experience — including a 2021 championship with Milwaukee — becomes a living blueprint for Portland’s young stars. While he likely wouldn’t stay in Portland for the long term, his presence injects a winning mindset into a roster desperate for structure. In a landscape where many rebuilding teams flounder without veteran stability, this version of the Blazers takes a different route: development by immersion.
It’s also possible that Portland flips Holiday again near the trade deadline, gaining further assets in return. His value around the league remains immense, particularly among contending teams.
Fit and Fallout: Celtics
The biggest question for Boston becomes defense. Losing Holiday — arguably the best perimeter defender in the NBA — creates a huge vacuum. Simons, despite his scoring prowess, has never been known for his on-ball defense or physicality. It would place more pressure on Derrick White and Jaylen Brown to anchor the point-of-attack defense, which could be problematic in playoff series against guard-heavy teams like Milwaukee or New York.
Offensively, though, Boston would be terrifying. Simons is a high-volume three-point shooter who can create off the dribble, push pace, and take pressure off Tatum and Brown in the half-court. Imagine a lineup of Simons, Brown, Tatum, Porziņģis, and Horford or White — there’s enough scoring to rival any team in the league, especially with Joe Mazzulla’s offensive spacing schemes.
It would require time and adjustment, but the upside is massive — and far more sustainable than their current veteran-heavy core.
Fit and Fallout: Trail Blazers
In the short term, Holiday’s arrival feels jarring. He’s not on the same developmental timeline as Scoot or Sharpe, and the Trail Blazers are not contenders. But the culture shift he brings cannot be overstated. With Holiday in the building, practices become more intense, expectations rise, and accountability spreads.
In fact, Holiday’s mentoring of Scoot could prove to be the most valuable aspect of the trade. Henderson, a high-energy young guard with franchise potential, gets to study under one of the smartest defenders and leaders in the league. The same goes for Sharpe, who continues to develop his two-way game.
And as mentioned, Holiday becomes a valuable trade chip in February if the team decides to pivot again. The potential return could include draft picks or a young asset better suited to Portland’s timeline.
Public Reaction: A Mixed Bag
Celtics fans would likely be divided. Many love Holiday’s grit and championship experience. Swapping him for a younger, less proven player could be seen as a step back. But others would welcome the move, excited by the thought of a more future-oriented “Big Three” of Tatum-Brown-Simons with room to grow together.
In Portland, reactions would hinge on Holiday’s intentions. If he embraces the mentorship role, the city could quickly fall in love with his work ethic and heart. If he angles for a trade, fans may feel the franchise missed a chance to build a young nucleus with Simons included.
Final Thoughts
In this reimagined trade, the Celtics take a bold leap toward long-term sustainability, betting that talent and time will outweigh experience. The Trail Blazers, meanwhile, embrace the power of mentorship and winning culture, even in a rebuild. It’s a rare case of a trade where both sides could win — not just in games, but in identity.
Whether either team would truly make this move in reality is debatable. But it’s hard to argue the intrigue it would bring to an already volatile and captivating NBA landscape.
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