Imagine your favorite NBA team being forced to make a heart-wrenching decision, not because of performance, but due to a financial straitjacket. That’s the reality the Boston Celtics are facing right now, and it’s sparking a debate that’s dividing fans and experts alike. Should the Celtics trade Derrick White for the No. 3 pick to escape the repeater tax trap? It’s a move that could reshape their future, but at what cost?
Bleacher Report’s NBA salary cap guru, Eric Pincus, has thrown a bold idea into the ring: a three-team trade that would send Celtics guard Derrick White to the Houston Rockets. The goal? To slash costs, reset the roster, and dodge the NBA’s brutal repeater tax penalties. But here’s where it gets controversial—this deal would mean parting ways with a core veteran in exchange for younger talent and financial relief. Is it a smart long-term play, or a risky gamble?
In Pincus’s proposal, White would head to Houston, while Boston would snag former No. 3 pick Reed Sheppard, Brooklyn forward Jalen Wilson, and a future first-round pick from the Rockets. Meanwhile, the Brooklyn Nets would land Fred VanVleet and a 2027 first-rounder from Houston. It’s a complex shuffle, but the financial upside for Boston is hard to ignore.
And this is the part most people miss: The Celtics are currently $12 million over the luxury-tax threshold, and the repeater tax—which doubles the penalty for every dollar over the limit—is making it nearly impossible to sustain their high payroll without deep playoff runs. Pincus argues that this season, with Jayson Tatum sidelined by injury and no serious championship aspirations, is the perfect time to reset. By dropping below the tax threshold, Boston could save nearly $39.5 million in taxes and earn a $12 million rebate from the league.
But why trade Derrick White for Reed Sheppard? At 31, White’s value is still high, but his recent struggles with efficiency and his age make this a strategic moment to explore a trade. Sheppard, just 21, is one of the league’s brightest young guards, averaging 10.4 points and 3.4 assists early in the season. Pincus sees him as a cost-controlled replacement who fits Boston’s evolving timeline. Plus, the Celtics would gain additional assets like Wilson and another first-round pick, all while slashing their payroll by $15.3 million.
Here’s the controversial twist: While the financial logic is clear, Boston’s front office remains reluctant to part with White. League insiders say the Celtics are demanding a king’s ransom for any deal—think the five first-round picks the Knicks gave up for Mikal Bridges. White’s two-way prowess and leadership make him a valuable piece, and trading him would be a tough pill for fans to swallow. But if Boston’s season falters, Pincus’s proposal might start looking less like a hypothetical and more like a necessity.
So, what do you think? Is trading Derrick White for financial relief and younger talent a smart move, or are the Celtics better off holding onto their veteran guard? Let’s hear your thoughts in the comments—this debate is far from over!
