Celtics' Free Agency Outlook and Top Contract Decisions Following Trade Deadline

The Boston Celtics had an eventful 2023 NBA offseason.

This summer could be plenty busy, too.

Now, maybe it won't be quite as active as last year's version, when the team traded for two starters (Jrue Holiday and Kristaps Porziņģis) while giving a third a historic payday (Jaylen Brown). But they could have to pay up to retain one of those acquisitions, and they just might end up inking another historic contract extension.

Oh yeah, and if everything goes to plan, they'll have a championship to celebrate, too.

While the players surely aren't looking toward the offseason yet, you can bet this front office is, so we'll do the same while examining where this team sits for free agency and dissecting two of the most important decisions they'll have to make.

Salary Outlook

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Boston, MA - February 27: Boston Celtics SG Jaylen Brown dribbles up-court in the first quarter. The Celtics defeated the Philadelphia 76ers, 117-99. (Photo by Danielle Parhizkaran/The Boston Globe via Getty Images)

The Celtics are fully in championship-or-bust mode, and their payroll reflects as much.

They have the least amount of projected cap space of anyone, per Spotrac. That's unlikely to change this summer, and honestly, they better hope it doesn't.

The only way that number dramatically changes is if Jrue Holiday declines his $39.4 million player option and heads elsewhere. A team with championship aspirations should not want to lose a two-way contributor like Holiday, especially since it would have no obvious means of replacing him.

The cuts wouldn't be as dramatic, but it could be tricky filling in frontcourt holes if Luke Kornet and/or Xavier Tillman leave in unrestricted free agency.

Jrue Holiday's Player Option

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BOSTON, MA - FEBRUARY 27: Jrue Holiday #4 of the Boston Celtics dribbles during a game against the Philadelphia 76ers at TD Garden on February 27, 2024 in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Adam Glanzman/Getty Images)

Holiday's 34th birthday will happen this offseason. His offensive volume has dropped to its lowest level in a decade-plus, and while that's mostly attributed to the talent around him, he could still head into the open market with quiet counting stats (13 points and 4.8 assists per game).

That's assuming he ever gets that far. Holiday told MassLive's Brian Robb he would like to get an extension done before the season ends.

"I'd like to be here," Holiday told Robb. "I feel like I'm getting more and more comfortable, loving the guys, loving the organization and loving the city."

Holiday seems likely to stay put, although it's unclear what kind of new contract he'll command. A deal that lowers his 2024-25 salary but keeps him around for the long haul feels like it makes the most sense for both sides.

Jayson Tatum's Extension

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BOSTON, MA - FEBRUARY 27: Jayson Tatum #0 of the Boston Celtics brings the ball up court during the game against the Philadelphia 76ers on February 27, 2024 at the TD Garden in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2024 NBAE (Photo by Brian Babineau/NBAE via Getty Images)

For the second consecutive season, the Celtics are likely to make a historic commitment to an All-Star wing.

One year after Brown cashed out, Jayson Tatum is set to do the same.

The five-time All-Star is supermax-extension-eligible, and one would think Boston would secure his future at the first possible opportunity. The 25-year-old is a perennial MVP candidate who looks like the key to unlocking this club's championship potential.

He's one of the top five-to-10 players on the planet, and he's probably months away from signing the richest contract in NBA history.