5 Trade scenarios the Celtics must prepare for this offseason

The Celtics need to monitor these trade scenarios after the Jrue Holiday extension.
Boston Celtics, Derrick White
Boston Celtics, Derrick White / Dale Zanine-USA TODAY Sports
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2. Ownership forces payroll trim

With Holiday’s new contract, they have $192 million committed in salaries and nine players on their books. The Celtics will be limited to minimum contracts in free agency, but even adding five more players gets them north of $200 million before factoring in the luxury tax payments and penalties for overspending.

Is ownership willing to spend that much? They are paying $39.7 million in luxury tax penalties this season with a projected bill of $47.7 million before filling out their roster. Celtics ownership will owe $250-plus million just on their roster alone next season. It is the price of contention, but a hefty one. 

They could mandate the franchise cuts payroll, which would leave Brad Stevens and the front office scrambling. It feels like Jaylen Brown is the most likely piece of their top six to be moved, but trading a prime three-time All-Star for salary relief is a tough sell to a title-contending roster. It is not the time to pinch pennies, but they cannot be above the second apron forever.

The spending is not slowing down. The Celtics need to extend Jayson Tatum and Derrick White, whose new deals will start in the 2025-26 season. Those further financial hurdles could force change.