Breaking down future Celtics player extensions with CelticsBlog’s Keith Smith

Throughout the Kevin Durant saga, one of the main factors that was constantly brought up was Jaylen Brown’s future with the Boston Celtics. He has two years left on his contract, but he is already due for a contract extension. However, he’s not going to sign one anytime soon, and it has absolutely nothing to do with the team.

I spoke with NBA cap expert Keith Smith of CelticsBlog and Spotrac about the Celtics players who will need extensions in the next couple of seasons. In addition to Brown, this conversation included Grant Williams, Al Horford, and Payton Pritchard. But of course, it all started with the star wing.

Brown’s upcoming extension

First, Smith laid out why Brown won’t be signing an extension this summer or next summer. If he did, he would be leaving millions of dollars on the table.

“It is not beneficial at all for Jaylen brown to extend now. This is not anything to do with the Celtics. The Celtics would love to extend him today. Because he is not on one of the so-called designated player extensions, Brown is not in a position to extend for the max like what we generally see a lot of other guys do… So in that spot, Brown is set to make $30.7 million in the final year, in the 2023-24 season. What he can do off of that number is he can extend for 120%, or a 20% raise off of that, for three years. Right now today, he could do that. That would make his number, let’s call it $36.9 million in 2024-25, $39.8 million in 2025-26, and then $42.7 million in 2026-27. Total, three-year extension, $119.5 million. If Brown waits to become a free agent, his first-year salary that he would be eligible for is $42.9 million. So, $42.9 million is, you know, that’s roughly $6 million above what he could make in an extension, then you add on the raises from there, and we go from there. So that’s why he’s not going to do the standard veteran extension this summer.”

Smith outlines the potential extensions Brown could receive in more detail here.

By waiting to become a free agent two years down the line, Brown will make significantly more money on his next contract. Signing a new deal right now would be financially irresponsible, even though Boston would likely prefer to ink him to a new contract as soon as possible.

That being said, the good news for Celtics fans is that Boston can offer him more money than any other team on the market. So teams hoping to steal Brown in free agency will already be at an immediate disadvantage. Smith noted that, while the starting salary would be the same wherever he signed, the Celtics can offer him better raises and an extra year on his deal.

“If he went to another team, the starting salary is the same, it’s still $42.9 million. The difference comes in, it can only be a four-year contract, and there can only be 5% raises. So you’re looking at a maximum of four years, $184.5 million. So, even if you did the four-year to four-year, he’d be giving up about $7.7 [million] total, but it’s that fifth year with a potential option on the end, that extra $64 million, that’s what really makes the difference.”

There’s always a chance that Brown prefers signing with another club, as is always the case with free agents, but in terms of financial gain, the Celtics have more to offer than anybody else.

But that’s not where the Brown extension talks end. Those numbers all account for Brown’s base salary would look like. However, if he ends up winning MVP, winning DPOY, or making an All-NBA team in the next two years, he would qualify for an even better starting salary.

“There are a couple of different things that can happen here. If Jaylen Brown wins MVP this season, wins Defensive Player of the Year this season, neither of those is probably likely to happen, or if he’s named to All-NBA this coming season, which maybe, right? I don’t think that one’s crazy. He would then be eligible for what people call the supermax extension… And that would be five years, $290 million, starting at $50 million in the first season, then it’d be $54, $58, $62, and then $66.”

As noted by Smith, it seems unlikely that Brown wins MVP or DPOY, but if he takes a jump and the Celtics are one of the best teams in the NBA, it’s not out of the question for him to make an All-NBA team. At that point, Boston could give him even more money.

And as a quick side note, I spoke with Smith about the increasing salary cap and what players are worth nowadays. Gone are the days when $30 million was a lot of money, and now, that’s what potential All-Stars are being paid. So while $50 million may sound like a scary amount of money to give Brown, that’s just what max deals are starting to become.

“I mean, $30 million contracts for players who are a, let’s just say, potential All-Star guy. Which I think if you sat down and made your list, right, well, what is it, 24 teams, 24 players make the All-Star Game every year. So you’d probably sit down, you’d probably build a list of 40 to 50 potential All-Stars in a season. That would be in that spot. That’s what the number is going to be on the low end.”

So before turning your head up at a $50 million contract, make sure to remember that the salary cap is always increasing. As Smith explained it to me, don’t think of $30 million (or even $50 million) as a raw number, think of it as a percentage of the cap, which will continue to rise.

Photo by Brian Babineau/NBAE via Getty Images

Williams’ upcoming extension

While Williams isn’t a max player like Brown or a potential All-NBA candidate, his contract situation is the more pressing one. Brown has two fully-guaranteed years left on his deal, while Williams’ contract is up at the end of the upcoming season.

The 23-year-old forward took a massive leap last year and is poised to play a huge role in Boston’s rotation again this season. He’s extension eligible right now, and according to Smith, we should start hearing more chatter about an extension for Williams as the October 17 deadline approaches.

“So 10/17. That’s the last day to sign a rookie scale extension. So, for Grant, we’re basically down to, call it a month and a half left to do that. Not uncommon. Normally, it’s your no-brainer max guys who come off the board first with those rookie scale deals. Then after that, you’ll see guys like RJ Barrett, right, not the full max. We did see Keldon Johnson get one done earlier, that’s a little bit uncommon. But usually, a guy like Grant, there’s not going to be the full max, that’ll take a little longer. A lot of times, what they want to do, they like to get those done right around the start of training camp or shortly thereafter. So my guess is probably, let’s call it a month from now, is when we’ll probably start really hearing something about an extension for Grant.”

Last season, Williams was one of the best three-point shooters in the league, and his versatile defense allowed him to be a staple in the Celtics’ lineup. Ime Udoka was comfortable playing him big-time minutes, which is huge for a coach that requires players to be passable on the defensive side of the ball.

He’s not going to get a max contract, but Smith believes that the numbers for Williams could surpass the $10 million mark.

“I think there’s potential that Grant gets something in the 12 to $13 million a year range for average salary. So you’d be starting probably somewhere between $10 and $11 million and then climbing from there. Similar-ish to what Rob[ert Williams] signed last year seems to make sense to me, given his role, how he’s improved year to year, you know, the fact that his game seems pretty projectable moving forward.”

And before fans start clambering about the comparison to Robert Williams, it’s important to remember the situation. Last year, Robert Williams was coming off of a 52-game season and two prior years of playing roughly 30 games. He was an injury-prone big man who showed flashes of potential, and now his contract looks like a steal.

Grant Williams played 77 games last year, averaged a career-high 24.4 minutes per game, and shot 41.1% from three-point range. Robert Williams may have a higher ceiling, but in terms of consistency, the price is right.

Also, while Boston has an opportunity to lock Williams into a new deal before he ever hits the open market, there’s always a chance that the two sides can’t come to an agreement. And as unlikely as it may sound, there could be teams out there willing to overpay for Williams’ services, as he’s still only 23 (24 on November 30). However, he will be a restricted free agent, so teams would have to pay him enough to make the Celtics balk at matching the offer sheet.

“I think if you want to get a guy in restricted free agency, generally you have to overpay for them. No one’s clearly gonna go to a max for Grant. I mean, unless he has some really ridiculous year this year. But as you look at the teams that project to have cap space, there’s a handful of teams that he could make sense on, that could pay him, you know, something in the $15 to $20 million a year range. I think if he was good enough to earn that kind of deal, then the Celtics probably think about matching and then figuring it out. However, they figure it out down the line.”

Smith also noted that Williams should expect to take on a larger role this year, which could have an impact on his value.

“I think they’re going to be very judicious cautious, I don’t know how you want to put it, with both Horford and Rob this year. Horford, we already saw, when it’s back to back or he needs a rest day, he gets a rest day. But I think with both of those guys, it’s going to be, you know, ‘alright, hey, they need a night, give them a night,’ and then that probably means Grant’s next up… So it’s kind of a big year for him.”

Despite many Celtics fans giving Williams the Marcus Smart treatment of “you love him or you hate him,” he’s very clearly a staple within the Celtics’ rotation. Paying him roughly $12 to $13 million per seasons puts him on part with players like Richaun Holmes, Robert Covington, and former Celtic Josh Richardson.

Photo by Adam Glanzman/Getty Images

Horford’s upcoming extension

Last time Horford’s contract in Boston was up, he left. He signed with the Philadelphia 76ers, was swiftly traded after one year, and then landed back in Boston, where he had a phenomenal season and was one of the most impressive playoff performers in the NBA. And he did it at 36 years old.

But that’s also the issue with a potential extension. By the end of next season, Horford will be 37 years old, and we’re already hearing rumblings that he won’t play in back-to-backs in the upcoming season. In turn, Smith thinks Boston could be very cautious with extending him.

“I think what you’ll see is probably something in the range of, let’s say, two years, $25 to $30 million. You know, where it’s probably split pretty evenly. Second year, maybe a team option, maybe a partial guarantee, something like that. I would be shocked if it’s anything beyond a two-year extension at this point, just because of where he’s at in his career. I think you want to be be very cautious.”

During the playoffs this past season, some reports came out saying Boston would be picking up Horford’s contract at the full amount for the upcoming season regardless of the stipulations. That means the big man will make $26.5 million in the upcoming year.

While it’s not an exact science, Smith believes that this could be the Celtics’ way of paying it forward, in a sense.

“He’s only guaranteed $19.5 million right now. And I think, for the Celtics, it’s, ‘hey $19.5 million, we’d be thrilled to pay you that for this upcoming year. $26.5 [million], that’s a little bit much.’ But I think what you almost do is, you take that extra $7 million, and you add that in as a, ‘hey, that’s a prepayment for the next couple of years.’ It’s it’s not really by any means. But I think that’s kind of what you’re looking at.”

Handing Horford the extra $7 million for next year could be Boston’s version of a preemptive “make-good” gesture to help with negotiations down the line.

At this point, Horford and the Celtics are pretty tied to each other. The last time he left, it didn’t work out, and the team is clearly better when he’s on it. So it’s tough to imagine negotiations going south, but there could be a potential waiting game left to be played, and it’s not out of the question that Horford decides to call it quits if Boston wins a title next year.

“They’re not going to be insulting and be like, ‘hey, you want to do a $5 million a year deal?’ or anything like that. Because I mean, he’s not going to do that either. I do wonder if there’s a little bit on both sides of, hey, let’s just play this year out knowing he’s probably not going to leave anyway, even in free agency, if he wants to play another year. And let’s see where it’s at. Because there is a world where I could see Al Horford, very easily saying, ‘hey, we won the title. I’m done. I’m going out on top.’”

However, that would then leave the Celtics in a bit of a tricky situation, but it’s one that they will have to deal with eventually. The post-Horford era will be a slippery slope, as Robert Williams has thrived when he doesn’t have to guard opposing bigs because of Horford’s presence.

Once that time comes, Smith believes Boston will begin to scour the open markets for bigs who can recreate a similar role to the one Horford plays.

“This is one of those ones where you start looking at what free agency looks like next summer. And, you know, the good news is there are a lot of those kind of bigger bodies that should be available, and I think what they’ll probably do is, if Horford’s gone, then what you do is you’ll say, hey, you know, Brook Lopez, Steven Adams. Jakob Poeltl. Can we snag one of these guys for the mid-level amount?”

Obviously, that’s a problem for another time, as Horford is still under contract for a year. But if Horford retires after this season, or needs to take on an even smaller workload, the Celtics should have plenty of options in free agency.

Photo by Garrett Ellwood/NBAE via Getty Images

Pritchard’s upcoming extension

Lastly, this is likely the least pressing of the four potential extensions, as Pritchard is under contract for two more seasons, and the Celtics are already loaded at the guard position. According to Smith, we’re too far out to start projecting any numbers in regard to a potential Pritchard extension.

“He’s not even extension eligible until next summer anyway. So, I think at this point, for all parties involved, it’s, let’s just see where this goes. I think it’ll be, you know, hey, all right, did we do we end up moving Derrick white in a different deal? Did Brogdon not work out, now he’s being moved on from? Either one of those things probably opens the door for Prichard to come back. I think there’s also a sense of, what does it look like a year from now with Jaylen?.. But thinking extension, projecting anything for him right now, I think it’s just too far out.”

Pritchard is currently stuck behind Smart, White, and Brogdon in the depth chart, so he has a tough path to regular minutes next season. But as explained by Smith, a lot can change in the matter of two seasons, so while Boston isn’t in a real rush to extend Pritchard, keeping him around is smart.

With how young he is and the uncertainty regarding his role, Pritchard’s contract value by the end of his current deal could go in a bunch of different directions.

“Is Pritchard going to be a $5 million point guard? Is he going to be a minimum point guard? Is he gonna have played well enough to be a $10 million a year backup point guard? I struggle to see much more than that for him.”

Smith also stressed the importance of picking up team options for players on rookie-scale deals, noting that Boston will likely pick up Pritchard’s fourth-year team option sometime soon.

“One of the things they have to do by October 31 is pick up his rookie scale team option for next season. I can’t see any reason that doesn’t get picked up… You should not decline rookie-scale team options unless one of two things happens – it is painfully obvious that the player stinks and cannot play at all and has no potential… or the guy is injured and you don’t think he’s ever going to be able to play… Other than that, pick those up, because [if you don’t], it’s only going to go badly for you.”

Conclusion

So with the way things look, the timeline for Celtics extensions could look something like this – Williams could ink one as soon as training camp, Horford’s will likely come next summer, Brown’s the following offseason, and Pritchard’s (with a big question mark) around the same time as Brown’s.

And, circling back to the point on most fans’ minds, just because Brown isn’t going to sign an extension sooner doesn’t mean he’s upset with the Celtics. The deal’s timing is a financial thing, not a Boston thing.