When are the contract extension deadlines for Derrick White and Payton Pritchard?

It’s been a whirlwind of an offseason for the Boston Celtics.

President of Basketball Operations Brad Stevens has meticulously executed a massive roster overhaul, with his latest acquisition being All-Star guard Jrue Holiday. Boston’s roster is almost complete, although the team does still have a couple of open roster spots with a noticeable hole to fill in the frontcourt following Rob Williams’ departure.

Outside of a potential big man addition, what you see is what you get with the 2023-24 Celtics, at least for the moment. Training camp is underway, with the first preseason game this Sunday against the Philadelphia 76ers.

Despite having limited roster moves left to make, there are still some crucial decisions for Stevens to consider over the coming weeks that don’t necessarily affect this season. Two key members of the team’s backcourt rotation are extension eligible, Derrick White and Payton Pritchard.

Here’s everything you need to know about those potential deals, with my thoughts on how feasible they could be.

Derrick White

Extension Deadline: October 23

Current Contract: 2 years remaining (2025 Unrestricted Free Agent) — 2023-24: $17.6 million; 2024-25: $18.8 million

White became eligible for an extension in September and last month, a deal seemed logical for both sides. Marcus Smart had been dealt and White was slated to move into Boston’s starting point guard role coming off one of the most successful seasons of his career.

However, following the Celtics’ acquisition of Jrue Holiday, the prospects of Stevens and White agreeing to a deal before the October 23 deadline seem slim. Holiday becomes extension eligible himself in February, and it has been reported by ESPN’s Adrian Wojnarowski that Boston is eager to reach a deal with the star guard. Stevens all but confirmed that report during Holiday’s introductory press conference on Wednesday.

Assuming that’s the plan, then the Celtics will have four players locked up long-term on massive deals in Holiday, Jaylen Brown, Kristaps Porzingis, and Jayson Tatum, who will be eligible to sign a supermax extension next offseason.

Boston is already over the second apron of the luxury tax, and while ownership continues to reiterate its commitment to paying for a contending product, there’s only so much they can realistically spend operating within the new CBA. For all the reasons listed above, a deal doesn’t seem realistic for the versatile guard prior to the deadline. It’s also worth noting that with two years remaining on his current contract, Stevens likely won’t feel rushed to reach an agreement.

Verdict: Extension unlikely this offseason

Payton Pritchard

Nathan Ray Seebeck-USA TODAY Sports

Extension Deadline: October 23

Current Contract: 1 year remaining (2024 Restricted Free Agent) — 2023-24: $4.04 million

The Celtics picked up Pritchard’s $4.04 million option for the upcoming year, setting him up to enter restricted free agency in the following offseason. That creates a bit more urgency for Boston to lock the young guard up than there may be with White, as the team knows all too well how tough it can be to retain restricted free agents (see Grant Williams).

The Athletic’s Jared Weiss recently reported that the Celtics have actually opened contract negotiations with Pritchard, although a sizable gap remains. That makes sense, as Pritchard’s limited minutes over the years have likely led Stevens to offer a contract lower than the guard thinks he’s worth.

If the two sides are able to come to an agreement before the October 23 deadline, an annual salary somewhere in the realm of the current non-taxpayer mid-level exception ($12,405,000) could be realistic.

There are pros and cons to a potential extension for Pritchard. On one end, if Boston is confident in his ability to successfully assume a full-time rotation role as currently projected, agreeing to a deal now could result in his contract becoming a steal, similar to the extension Stevens signed Rob Williams to a couple years ago. However, if they do give Pritchard non-taxpayer MLE money and he ends up falling out of the rotation, that deal could become ugly quite quickly.

That said, it never hurts to have players locked up on “tweener” contracts, as it helps with salary matching in future trades. Stevens appears to be legitimately high on Pritchard’s chances of becoming a serious factor for the Celtics this year, and if that’s the case, an extension is certainly feasible.

Verdict: Realistic chance of an extension this offseason

With the deadline for these extensions less than three weeks away, it will be fascinating to see how negotiations play out for each of Boston’s guards, especially after another crucial backcourt player was added to the rotation.