Derrick White and 3 others leaving the Boston Celtics for his old team, the San Antonio Spurs, has become more plausible after the Cs signed Jrue Holiday to a four-year, worth $135 million

Derrick White leaving Boston Celtics for old team more plausible after Jrue Holiday extension

Boston Celtics v San Antonio Spurs
Boston Celtics v San Antonio Spurs / Ronald Cortes/GettyImages
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Derrick White leaving the Boston Celtics for his old team, the San Antonio Spurs, has become more plausible after the Cs signed Jrue Holiday to a four-year, $135 million extension on April 10 according to Air Alamo’s Jahlil Williams.

“The possibility of Derrick White returning to the San Antonio Spurs has sparked intrigue among fans, with rumors circulating about a potential reunion with the team,” Williams prefaced before saying, “With the Boston Celtics facing salary cap constraints following their recent contract extensions, the opportunity for White to return to San Antonio has become more plausible.”

White is a free agent in 2025, and after Holiday’s extension, there could be a tax crunch that summer for the Celtics. Winning it all this June could convince Wyc Grousbeck to pay any tax bill that Brad Stevens creates through his transactions. Anything short makes doing so a risky proposition.

Derrick White leaving Boston Celtics would give Payton Pritchard make-or-break opportunity

White leaving the Cs next summer is far more on the table than ever with Holiday being extended, and in the event that happens, Payton Pritchard would have a make-or-break opportunity to step up and be the team’s leading floor general. That is, unless Boston got a starting quality point guard back in return.

Pritchard is the third-longest tenured Celtic, if you don’t count Al Horford’s first stint that had two interrupted seasons with the Philadelphia 76ers and OKC Thunder in 2019-20 and 2020-21, and has evolved into a game-changing presence on the floor.

White has been the C’s primary ball-handler, with Holiday shifting to the 2 and sometimes even the 3-5 positions — so Pritchard would be sliding into No. 9’s role, not Holiday sliding down and bringing someone like Sam Hauser into the starting five.

The chance of a lifetime could be waiting Pritchard if Boston does something very unpopular but cost-saving in 2025.

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Jrue Holiday signs four-year, $135 million extension with Boston Celtics: Reaction, grades

By Andrew Hughes

Boston Celtics v Charlotte Hornets
Boston Celtics v Charlotte Hornets / Jacob Kupferman/GettyImages

 

A Woj bomb shook the foundations of the Boston Celtics fanbase on April 10 with the announcement that Jrue Holiday signed a four-year, $135 million extension with the Cs 10 days before the start of the NBA playoffs.

As ESPN’s Adrian Wojnarowski pointed out, Holiday joined rarified air with his historic extension at the age of 33.

“Holiday will become the fourth player to sign a fully guaranteed deal worth more than $100 million at 33 or older – a list that also includes LeBron James, Steph Curry and Al Horford,” Wojnarowski wrote just after breaking the story.

Boston Celtics get an A grade for Jrue Holiday extension because of its timing

Getting Holiday at $135 million isn’t exactly a steal, since he didn’t take much of a paycut from his $37 million salary for the 2024-25 season, but the timing of it makes it a total win for the Celtics; who know don’t have to worry about any chemistry issues in the offseason with all their key pieces locked in for at least next season.

The one question mark is Derrick White, who now seems to be the odd man out in the offseason if the Cs fall short. Expect a White trade if Boston somehow bows out before the Finals or Eastern Conference Finals. If the team wins, White may be entitled to ask for a similar salary figure over as many years, potentially bloating the team’s payroll to a somewhat asinine degree. Ditto for Kristaps Porzingis, who will be getting $3-4 million less over the next years than a player he has outperformed in 2023-24.

In truth, though, no one should be expecting a trade in the offseason. Holiday’s long-term future being secure could be the chemistry-sealing move Brad Stevens needed to make before the Celtics embarked on their most important playoff run in recent memory.

Banner 18 feels closer than ever with the team’s lone champion getting perhaps his final big payday just before the playoffs. That’s going to be a happy man who will be ready to produce.

 

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