Jayson Tatum’s extension gives Boston a historically expensive roster, so how long can they keep him?

The Boston Celtics’ contract extensions to Jayson Tatum and Derrick White on Monday were a no-brainer. White will make about $30 million less than Immanuel Quickley over the next five years because the collective bargaining agreement capped how much Boston was legally allowed to pay him. White is the better player, and Boston got a discount.

Tatum didn’t exactly give the Celtics a discount, but the super max for a First Team All-NBA player in his 20s is a fair market value. Keep in mind that the new TV deal is expected to increase the salary cap by 10% per year. Tatum’s contract will include the maximum allowable annual raises of 8%. a relative basisThis contract will seem less and less expensive with each passing year.

But those two contracts, along with Boston’s pre-existing contracts for Jaylen Brown, Jrue Holiday and Kristaps Porzingis, will make the Celtics one of the most expensive teams in NBA history for years to come. Cap expert Yossi Gozlan projects Boston’s total payroll and luxury tax for the 2025-26 season to be about $438 million…and that doesn’t include a potential new deal for Al Horford, if he’s still playing at that point. That puts Boston well behind Phoenix’s projections for 2025-26, but it’s still a huge price to pay for any NBA roster, and one that very few teams could sustain for long.

Short-term payments aren’t the only problem here. There are three other mitigating circumstances at play:

• Celtics owner Wyc Grousbeck announced Monday that he plans to sell his stake in the team. Grousbeck has always been willing to pay the winners’ tax. He approved extensions for Tatum and White. But we have no idea what a new owner would be willing to spend on the roster. Sometimes you have a Mat Ishbia, who is willing to throw caution to the wind for a good chance at winning. Sometimes you have a Tilman Fertitta, who let Trevor Ariza go on a one-year deal despite his Rockets coming close to winning the championship the year before.
• The second apron penalizes teams in ways that go beyond the owner’s pocketbook. It severely limits your ability to make roster changes. Maybe the Celtics are happy with their current roster over a long-term window, but even if that’s the case, the most damaging element of the second apron comes in the form of the draft freeze. When you cross the second apron line, your first-round pick in seven years is “frozen,” meaning it can’t be traded, and if you stay over the line for more than two consecutive seasons, that pick automatically drops to the bottom of the first round. This penalty is so steep that even teams willing to pay the second apron tax are generally expected to do so for only two years before moving back down to protect their future picks. This is also not a situation where you can go below the line for a year and reset the clock. Once you finish a season as a second-tier team, you must stay below the line for three of the next four seasons to avoid the pick drop.
• The luxury tax formula is going to change starting in the 2025-26 season, and it’s going to be especially punitive for repeat payers like Boston. Under the old system, the repeat tax started at $2.50 for every dollar above the line a team spends in the first $5 million. That number then jumps to $2.75 for the next $5 million, $3.50 after that, $4.25 after that, and then for every additional $5 million, the tax rate increases by an additional 50 cents per dollar. It’s already an extremely expensive system, but it’s about to get a lot more expensive. The new repeat tax penalty starts at $3 for every dollar above the tax line a team spends in the first bracket. The next bracket only goes up to $3.25… but after that it goes up to $5.50, then $6.75, and finally it adds an extra 50 cents on the dollar for each additional bracket after that. Historically, these brackets were set in $5 million increments. Going forward, they will increase in line with the salary cap, giving teams a little more wiggle room to climb the standings. But overall, it will be much more expensive for teams like the Celtics to operate well above the tax threshold, even if they are willing to accept the on-court consequences.

Putting it all together, it’s hard to imagine the Celtics keeping this entire group for more than a few years without making some concessions. So how long could the Celtics compete with this group of players?

If Boston wants to stick around for the long haul, it first has to get down for the 2024-25 season. It will be nearly impossible to get down below that for the 2025-26 season, so Boston has to move the clock back a year. The second line has been set at $188,931,000 for next season. Currently, the Celtics owe 13 players (including rookie Baylor Scheierman, who has not signed but will likely make 120% of his salary, as is the industry standard) $194,337,300, according to Spotrac.

There are going to be some cuts to make right now. If the Celtics can get rid of Payton Pritchard in someone else’s salary cap or a trade exception, they can get back under the line with an incomplete roster. That would put them at $187,640,871. However, they would need to add at least two more players at the rookie minimum to field a full 14-man roster. The rookie minimum for next season will be $1,157,153, so two of those players puts the Celtics back above the line at $189,955,177.

Still, we’ve closed most of the gap. The easiest way to close the rest would be to trade Jaden Springer and his $4,018,363 salary. Not only would that give the second-stringers some breathing room, it would also give the Celtics a bit more choice in the type of free agents they could pursue to fill out their roster. For example, they could opt to sign a more experienced free agent for the higher veteran minimum salary of $2,087,519 in this scenario.

In a perfect world, the Celtics would fix this here and now. Technically, though, they would have all season to fix it. They could instead try to get rid of the money at the trade deadline, which would open up different avenues for them. Imagine, for example, that Al Horford, who is 38, suffers a major decline or a serious injury next season. In that case, maybe getting rid of his $9.5 million salary would be more acceptable than getting rid of the young Pritchard. In all likelihood, the Celtics would factor that into the season and try to fix the problem then. It’s a risky approach.

Just look at what Denver is going through right now. The Nuggets signed Zeke Nnaji to a four-year, $32 million extension last offseason, which seemed like a no-brainer at the time. This offseason, they had to frantically try to get rid of him in order to potentially free up space on the second deck to sign Kentavious Caldwell-Pope. They couldn’t. Generally speaking, it’s advisable to err on the side of caution when it comes to the second deck. There are teams with salary cap space now (with Detroit standing out as the most obvious) that could help Boston solve its deck problems. That may not be the case come February.

The 2025-26 season, as we’ve seen, is likely a lost cause from a second-tier perspective. Gozlan estimates that the second-tier will bring in about $208 million. The Celtics already owe their starting five about $198.5 million. If Tatum, Brown, Holiday, White and Porzingis are on the team, the Celtics will be a second-tier team. Frankly, they might even throw caution to the wind for the 2025-26 season.

Could they keep Pritchard? Sure. How about a new contract for Horford? If he wants one and deserves it, why not? There have even been rumors that Boston could extend Sam Hauser, who would likely have trade value on a new deal, so sure, go for it. The 2025-26 season, in all likelihood, will be Boston’s most expensive, but knowing that in advance allows the Celtics to at least prepare for it. They’re going to find another way to avoid the second-round draft penalty, so you might as well spend the money in 2026 to maximize your title chances that season.

The 2026-27 season is likely the turning point for Boston. Porzingis will become a free agent in the summer of 2026. If the Celtics were able to avoid the 2024-25 second draft, they would potentially be open to bringing him back on a one-year deal, as they would still have one more year of second draft time allowed before the draft penalty is upheld. But what are the chances that Porzingis, who will be 31 at the start of the 2026-27 season, will agree to a one-year deal? Boston could re-sign him at market value and then look to trade him before the 2027-28 season, but given his injury history, that’s a huge risk. That’s around the time we should expect the Celtics to suffer their first significant loss. They’ll be able to carry their core into the 2025-26 season. Depending on how the 2024-25 season goes, they might even be able to extend the contract through the 2026-27 season. But someone will have to leave at that point.

The short answer to the question “how long can the Celtics hang on” is either two or three years. That’s how long the second apron should allow this version of the team to stay together, and it’s enough time to form a dynasty, if the Celtics stay healthy and as dominant as they were last season. The important thing to note, above all, is that a lot can change between now and, say, the summer of 2026. Porzingis is the easiest player to predict as a trade because of his shorter contract and injury risk. But for all we know, the Celtics are forced to trade Brown or Holiday in a year or two for reasons we can’t predict. The NBA is chaotic. Who would have expected Klay Thompson to ever leave the Golden State Warriors? Weird things happen.

The Celtics are good enough to weather these storms. This team was built for a three- or four-year window, and they managed to get through the first year with a trophy to show for it. If they play well, they could have more trophies to show for it. They’ve built a near-perfect core roster, and almost everyone is paid fairly or on a team-friendly contract. But no streak lasts forever in the modern NBA, and even if it’s only years away, the Celtics will have an expiration date of some sort. Tatum, Brown, and White are young and healthy enough that the Celtics could potentially reorient around them in the future, but they won’t keep their current starting five in place forever.