Celtics’ Immediate Anfernee Simons Plan After Jrue Holiday Trade

Originally posted on Athlon Sports | By Matt John | Last updated Jun 24, 2025 1:50 PM ET

The Boston Celtics have started their wheeling and dealing this offseason. ESPN's Shams Charania was the first to report that the Celtics have traded Jrue Holiday to the Portland Trail Blazers for Anfernee Simons.

This is a full-circle trade, as the Trail Blazers traded Holiday to the Celtics in 2023. Holiday went on to become the Celtics' last piece of their championship puzzle, but because of how expensive and lengthy his current deal is, Boston's trading him away felt inevitable.

Doing so helps the Celtics save money on their luxury tax bill, but they are still above the NBA's second tax apron. The biggest benefit from this trade is that Simons' deal expires in 2026, compared to Holiday's, which will expire in 2028.

While Holiday is gone for now, it's not set in stone that Simons will suit for the Celtics at the start of the 2025-26 season. The Boston Globe's Adam Himmelsbach revealed that while they like their newest player, they are open to anything this offseason.

"A league source said the Celtics acquired Anfernee Simons, who is on an expiring deal, because they like what he can bring to the roster, but added that they will 'remain engaged on all fronts,'" Himmelsbach wrote.

A league source said the Celtics acquired Anfernee Simons, who is on an expiring deal, because they like what he can bring to the roster, but added that they will "remain engaged on all fronts."
— Adam Himmelsbach (@AdamHimmelsbach) June 24, 2025

Simons will be owed almost $27.7 million for the 2025-26 season. Even if that's cheaper than Holiday, it's still an expensive contract. Boston will try to trade more players to get under that second tax apron. Despite what Simons can do, he just might be one of those players.

This article first appeared on Athlon Sports and was syndicated with permission.

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