Bleacher Report’s NBA salary cap expert Eric Pincus has floated a daring three-team trade proposal that would send Boston Celtics guard Derrick White to the Houston Rockets in a move designed to cut costs, reset the roster, and ease the financial strain of the league’s punishing repeater tax penalties.
The trade idea, which Pincus published this week, would see White — one of the Celtics’ core veterans — shipped to Houston, while Boston would receive former No. 3 pick Reed Sheppard, Brooklyn forward Jalen Wilson, and a future first-round pick via the Rockets.
In the proposed framework, the Rockets would acquire White and forward Haywood Highsmith from Brooklyn, while the Nets would get Fred VanVleet and a 2027 first-rounder from Houston.
Financial Pressures Behind a Hypothetical Celtics ‘Soft Tank’
Pincus argued that Boston’s front office could use this season as a strategic reset after injuries and payroll constraints altered its championship trajectory.
“Celtics fans are just coming to grips with the notion that the team is ‘soft tanking,’” Pincus wrote. “The practical and financial realities of Jayson Tatum’s injury and massive repeater tax and apron penalties led the franchise to trade away championship core players like Jrue Holiday and Kristaps Porziņģis.”
Even after offloading significant salaries, the Celtics are still roughly $12 million over the luxury-tax threshold, according to Pincus. The NBA’s repeater tax—which doubles the tax rate to $2 for every dollar spent over the limit—has made it increasingly difficult for teams to sustain high payrolls without deep postseason success.
“In a down year, without serious postseason goals, now would be the ideal time to drop below,” Pincus explained. “The Celtics could save nearly $39.5 million in tax payments and earn an estimated $12 million rebate for falling under the threshold.”
Why Trade Derrick White for Reed Sheppard?
Getty Reed Sheppard of the Houston Rockets reacts after scoring a three-pointer against the Utah Jazz.
Pincus acknowledged that moving White, 31, would be unpopular among fans but argued that the long-term benefits could outweigh the short-term loss.
“White is already 31,” he wrote. “The Celtics can use this opportunity to get younger at guard. Reed Sheppard was among the top-rated prospects in the 2024 NBA.com GM Survey. Boston can afford to let him learn on the job in ways that the contending Rockets cannot.”
White has struggled to adjust to a larger offensive role, averaging 15.0 points on just 30.8% shooting. Given his age and recent decline in efficiency, the Celtics could be better off exploring a trade while his market value remains high.
Sheppard, 21, has emerged as one of the league’s most promising young guards, averaging 10.4 points and 3.4 assists early in the season. Pincus described him as a cost-controlled replacement who fits Boston’s evolving timeline.
“The Celtics also get a look at Wilson from Brooklyn and an additional first-round pick,” Pincus added. “The payroll drops from about $200 million to $184.7 million, eliminating about $39.5 million in taxes. Teams below the tax also receive a kickback from the league, an estimated $12 million bonus to Boston. The Celtics also gain a significant trade exception to help reconfigure the roster next offseason.”
Boston’s Reluctance to Move White Remains Strong
Despite the financial logic, league insiders say Boston remains resistant to parting with White. According to NBA insider Jake Fischer, the Celtics have set an extremely high bar for any potential deal—requiring a package similar to the five first-round picks the Knicks gave up for Mikal Bridges.
White is signed through the 2026–27 season on a four-year, $125 million contract extension. He remains one of the league’s best two-way guards, averaging 15.2 points and 5.3 assists last season.
Brett Siegel of ClutchPoints reported in July that multiple teams offered substantial assets for White, including two first-round picks and a swap, but Boston rejected those offers.
For now, the Celtics appear focused on maintaining continuity around Jaylen Brown and White while Tatum is recovering from his Achilles injury, even as financial pressures continue to mount. But if Boston’s season stalls, Pincus’ proposal may begin to look less hypothetical — and more practical.
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