Boston Celtics' Jrue Holiday extension opens door for blockbuster trade before 2025-26 tax crunch

Miami Heat v Boston Celtics
Miami Heat v Boston Celtics / Maddie Schroeder/GettyImages

The Boston Celtics re-signing Jrue Holiday to a four-year, $135 million contract opens the door for the team to make a blockbuster trade ahead of a tax crunch for the 2025-26 season -- specifically, one involving Derrick White, the other backcourt starter due for an extension the offseason preceding it.

"Ultimately, the looming question here are going to be settled by White’s priorities," MassLive's Brian Robb prefaced before saying, "A team-friendly extension would certainly get done this offseason if he’s open to it but would he be willing to take it if there’s a possibility he could be dealt down the road during a luxury tax crunch looming ahead of the 2025-26 season. Only Boston’s ownership knows what type of payroll they will be able to handle at that point just as super max deals kick in for Jayson Tatum and Jaylen Brown."

The possibility of dealing White is a tough pill to swallow right now considering how vital his growth has been for the Cs. His arrival helped continue a turnaround in the second half of the 2021-22 regular season; a turnaround that ended in a 2022 Finals berth, and he is far from the forgotten starter in Boston's star-studded quintet.

Luckily, though, there is an easy solution that'd justify keeping him in a Celtics uniform.

Boston Celtics winning it all would justify spending any amount to keep core together

The Celtics raising Banner 18 in the TD Garden this summer would justify any spending Wyc Grousbeck would have to do and Brad Stevens would set up for him. A historical franchise that is starving for glory in the past 16 years, the Cs winning it all would cure all ills and justify any price tag.

With how effective the Celtics front office has been finding cheap pieces around their top six players, putting the eggs in their basket isn't the risk it could've been otherwise.