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Payton Pritchard #11 of the Boston Celtics

It’s not as pressing an issue for the Boston Celtics as whether to trade for Giannis Antetokounmpo or whether to test the trade market for Jaylen Brown (or perhaps both). But it is a long-term issue the Celtics will be monitoring in the offseason, as their time with what is widely regarded as the best contract in the NBA begins to run short. The Celtics were able to buy low on Payton Pritchard, but by the time the team takes the floor again next fall, he will have made a significant decision.

That decision: Whether to sign the three-year, $67 million extension the Celtics will offer him on October 1. As one person around the team put it when asked about whether Pritchard would sign: “Fingers crossed.”

Pritchard is coming off a year in which he averaged 17.0 points and 5.2 assists, making 37.7% of his 3-point tries, after having won Sixth Man of the Year last season. But he is in the middle of a four-year extension which sees him being paid $30 million, total. That contract is in stone, but Pritchard is expected to get a very big raise on his next deal.

Celtics Could Offer Around $67 Million

The fact that Pritchard is on a bargain deal now means the Celtics are limited in what they can give him in his next deal–unless he waits until he hits free agency. At most, the team can offer him 140% of what is estimated to be the average NBA salary at the end of his contract, and while it can’t be said for sure where that number will land, $67 million total for a three year extension is about where the Celtics’ offer would be.

That would probably still leave Pritchard as underpaid. But the Celtics would very much like to get him locked up in that new deal, and he might be willing to accept it on the basis of the security it provides going forward–the deal would be guaranteed, even if Pritchard is injured. Pritchard has given no indication that he would want to play anywhere but Boston, though it should be pointed out that his deal is set up for free agency in 2028, which happens to be when his hometown Seattle team could be back in business in NBA expansion.

Payton Pritchard Has Incentive to Wait

While the possibility of a Seattle return could be one reason for Pritchard to turn down a contract extension with the Celtics, sheer financial benefit is another. Pritchard has established himself as a top-level bench and role player, and probably could get a contract worth more than the $21 million or so he’s projected to start at.

As one executive told Heavy last month, “hardball” might be in his best interest.

“He is probably wise to wait on any extension he is going get offered from the Celtics. He probably wants to stay, he is such a perfect fit for their personnel and he does not seem like a guy who is out there wanting more shots, more minutes, more touches. He knows his role.

“But look, everything is going up in two years–salary cap, tax line. There will be more money, there will be more free-agent money, too. So if you’re Pritchard, why would you sign with the Celtics now? Play hardball. Whatever money they offer now is going to be there later. Security and injury, those are good reasons to take the money. He can make more though, by waiting. And there is only the slimmest chance he would make less.”