What Should Payton Pritchard's Extension with the Boston Celtics Look Like?

He is a high-level performer who has worked hard to earn a big extension, but the extension also covers years that typically mean a sharp decline for small guards

Apr 26, 2026; Philadelphia, Pennsylvania, USA; Boston Celtics guard Payton Pritchard (11) reacts after making a three point basket against the Philadelphia 76ers during the second half at Xfinity Mobile Arena. Mandatory Credit: Eric Hartline-Imagn Images | IMAGN IMAGES via Reuters Connect

Jordan Walsh’s extension with the Boston Celtics (not long after Neemias Queta got one himself) left one more big piece of business to be done this summer: Payton Pritchard’s contract extension. 

He’s eligible for a three-year, $67 million extension on October 1. There has been some reporting that the Celtics would offer that contract immediately to lock Pritchard up, but there are still some questions about whether they should. 

There's no doubt Pritchard has been fantastic for the Celtics. He won Sixth Man of the Year two seasons ago and would have been in the running for it again if he hadn’t started so many games at the beginning of the season. He’s been a reliable bucket-getter during the regular season, which was a very underrated reason why the Celtics were able to win 56 games last season. 

Still, the new CBA has changed things. I wouldn’t be writing this under the old system. Under this one, the Celtics have to play hardball with all of their contracts, because dollar counts. Miscalculating on any big contract could cause some problems. 

Small Guards Age Poorly

Let’s start with the biggest potential issue here. Pritchard’s birthday is in the middle of the season, which means he turns 29 in the middle of this season and 30 in the middle of next season. An extension would cover his 31, 32, and 33-year-old seasons. 

Small guards like Pritchard, who is 6-1, don’t tend to age well past 30. While Pritchard has been durable, he also likes to get into the paint and mix it up amongst the trees. There's a lot of opportunity for the athleticism to get sapped more quickly than expected. 

The CBA is Changing Things

We’re already starting to see fewer teams with cap space and fewer teams spending past the second apron. As of right now, no team is projected to spend into the second apron this upcoming season, which means money is going to be limited. 

Teams have to take into account the risk of losing a player in free agency when it’s time to hand out extensions. Pritchard has been great these past two seasons, and he might continue to be over the next year or two, but how many teams are going to use their cap space to lure Pritchard away when he’s 31? 

It’s obviously too soon to tell who will be available then, but I don’t know that Pritchard is going to top anyone’s free agent list in 2028. If only a few teams have cap space, there's more of a chance he’ll be floating around the mid-level than anything else. 

“Optionality”

The Celtics need to be able to pivot quickly, which means being able to move contracts in a pinch when something presents itself. Signing Pritchard to a contract worth $20-plus-million isn’t the worst thing in the world when it comes to trades, but it also removes the possibility of trading him into someone’s Mid-Level Exception, which can now be used as a Traded Player Exception as well. 

By trading someone into a TPE, the Celtics not only have the option of moving a player on his own, they could also create a TPE of their own for that amount. In this world of “optionality,” which Brad Stevens hammered home at the beginning of the month, I’d rather skew towards a plan that gives Boston more options down the road. 

That's not to say that a $22 million contract is untradable. Those have value in salary matching situations, so signing Pritchard to the maximum amount wouldn’t hamstring them. It just removes a couple of options. 

Conclusion

I need to reiterate at this point that Pritchard has been a fantastic player. He is one of the league's hardest workers, a high-level performer on the court, and a plus in the locker room. Under different circumstances, there would be no need for this discussion.

He should be rewarded for what he has done, and he is built, physically and mentally, to buck the trend that has befallen other smaller guards. Giving him the full amount is by no means an egregious error. A full three-year, $67 million extension is fine. 

But any kind of contract negotiation tends to highlight negatives. In this pseudo-negotiation, I’m looking at a great regular season player who is less effective in the playoffs, who is smaller, and getting older. I would prefer Boston give him a contract starting at the projected MLE for the 2028-29 season. A three-year deal that pays him $16.6 million in the first year is a better representation of what he could get on the open market. In fact, I’d be open to giving him a fourth year as a reward for taking the shorter money in the short term before I go too high in the first year of the deal. 

Wherever the numbers land, the extra savings will matter to the Celtics. They just made it clear with the Jaylen Brown trade that production has to match salary, and there is too much risk that Pritchard’s production will taper off during this extension to give him too much salary. 

Pritchard has done very well for himself to guarantee a big payday north of $50 million. Even what we would consider a team-friendly offer is going to be a significant amount of money moving forward. There's a number south of the maximum amount that will be a win-win for everyone.