Glory is loud, but uncertainty whispers louder when the confetti settles. The Boston Celtics, fresh off their heartbreaking 2025 postseason run, now stand at a crossroads. This summer could shape their future more than the ring ever did. Words like second apron, repeater tax, and roster crunch now echo louder than the victory parades they didn’t have this year. Talks swirl around potential exits for Kristaps Porzingis, Jrue Holiday, and even Finals MVP Jaylen Brown. So, they must make tough calls before chasing another banner, even if Jayson Tatum is out for most of the next season.
The bill is very real for the Celtics, who are officially in their offseason. They went just over the second apron this year by 4.4 million dollars. That alone triggers a $53.5 million tax payment. Painful, but manageable. However, Jayson Tatum’s looming extension changes everything. Next season, Boston will most likely overshoot the second apron by $20 million. If unchanged, that spike could balloon their tax bill to over $238 million. This situation will throw them into a state of roster restriction and freeze their draft picks for at most 7 years.
Celtics insider Keith Smith shared a key detail. If Boston stays above the second apron in 2032, their first-round pick drops to the end of the round. The league sets the order by reverse standings. Among teams like Phoenix and Minnesota, the worst team picks first. “Now, to avoid that restriction as well as to unfreeze the pick—or as I like to call it, thaw it out, because it doesn’t happen instantly—it takes a little bit of time,” Smith informed. “You have to be out from underneath the second apron in three of the immediately following salary cap years of the pick becoming frozen.”
Mar 14, 2025; Miami, Florida, USA; Boston Celtics forward Jayson Tatum (0) reacts against the Miami Heat during the third quarter at Kaseya Center. Mandatory Credit: Sam Navarro-Imagn Images
The insider further noted, “If it gets frozen, which it is now, and the Celtics are out, less than or equal to the second apron, in three of the next four years (league years), then the pick would become unfrozen. It falls wherever it would fall in the draft and can be traded again. That’s how you can thaw that pick out.”
As a second apron team, the Celtics cannot combine contracts to chase a pricier player. No salary stacking, no cash sweeteners either. It gets even tighter. Boston can only take back exactly what they send out in salary, nothing more. Meanwhile, non-tax teams enjoy a 125% plus $250K cushion. For the Celtics, even a single extra dollar breaks the rule, as there is zero flexibility.
Moreover, the franchise is staring down a staggering bill heading into the 2025-26 season. With salary and tax penalties combined, the total could approach $500M. Sitting above the second apron comes with harsh consequences. That kind of pressure leaves Brad Stevens little choice; expect him to be active on the trade front. Now, with Jayson Tatum out for 2025-26 due to an Achilles tear, Stevens might shift focus to trimming the roster bill.
In Jayson Tatum’s absence, will the Boston Celtics consider trading Jaylen Brown and two others?
To begin with, the Celtics need to chop off around $40 million from next year’s salaries. Some candidates for the purpose are: Jrue Holiday ($32.4M), Kristaps Porzingis ($30.4M, expiring contract), Derrick White ($28.1M), and Sam Hauser ($10M). So, Keith Smith said, “A Holiday move is possible. What I’ve been saying about Porzingis and Holiday—and I apologize if I’m stepping on a future question here—is that Porzingis is very acquirable for a lot of teams because he’s on an expiring contract. Those have value again.”
Some teams may not feel the apron heat yet, but they see it coming. So they might try to dump long-term contracts now while they still can. This is where Kristaps Porzingis could be a key for them. With his expiring deal, he becomes an easy sell. Teams can clear future cap space without much fuss. It is a clean break with upside. Meanwhile, “Holiday has a smaller market of teams, but the teams who want him or where he makes sense are going to be more motivated to try to get him.”
Now, Jaylen Brown‘s future is a hot topic now that Tatum is sidelined. Some fans want a full reset and see trading Brown as the way forward. But Boston likely sees him as central to a gap year, not a rebuild. His knee issues and massive contract may scare off suitors. Still, many teams would leap at the chance. If Brad Stevens ever tests the waters, he will not be waiting long for offers.
A dynasty never crumbles in one loud crash. It fades through tough choices, silent goodbyes, and numbers that never lie. With Jayson Tatum sidelined and Jaylen Brown carrying the crown alone, the Celtics now walk a fragile line. They can reset, retool, or risk it all again. Either way, Brad Stevens must act fast before the weight of dollars and doubt pulls it all apart.
The post Not Jayson Tatum, but $500M Celtics Headache & NBA Punishment Trigger Major Concern for Jaylen Brown & 2 Others appeared first on EssentiallySports.
