Saturday, September 5, 2026
The FOS App is Live Download It Now

The All-In Celtics Are Suddenly on the Brink

Boston’s roster could cost around $500 million next season if they don’t trade away any core players.

Jayson Tatum
David Butler II-Imagn Images

The Celtics could be facing their reckoning sooner than anyone anticipated.

The defending NBA champions fell to the Knicks 91–90 on Wednesday night to go down 2–0 in the series before it heads to Madison Square Garden this weekend. In both games, the Knicks have overcome 20-point deficits to win. 

Boston went all-in on this title window, handing out the two richest contracts in NBA history for co-stars Jayson Tatum and Jaylen Brown. Those two deals alone are worth more than $600 million over the next five years.

This year’s team cost $193 million, plus an estimated $50 million in luxury taxes. That total trails the Suns and Timberwolves for this season, but it’s next season when the bill really comes due. Keeping this roster intact could cost about $500 million when the NBA’s luxury tax is accounted for.

It’s unlikely that any ownership group would be willing to foot that bill, and the Celtics are in the process of being sold. So this spring’s playoffs have taken on an extra urgency. While the Brown/Tatum duo is here to stay, they might not have another supporting cast stacked with expensive players like Jrue Holiday or Kristaps Porzingis again. Both Holiday and Porzingis are set to make more than $30 million next year and are prime candidates to be traded to shed salary.

For both games of the Eastern Conference semifinals, the Celtics have looked like the more dominant team, holding a double-digit lead for most of the game only to let the Knicks rally and pull it out in the end. The Celtics, known for hoisting 3s, aren’t making many, shooting just 25% from deep in their first two games. 

If the Celtics stand pat, that would mark their second straight year in the league’s dreaded second apron. Being in the second apron for three years in a five-year span would move their first-round draft pick to 30th, take away their mid-level exception to use in free agency and prohibit the use of trade exceptions in transactions, all of which make it harder to stay in contention. 

Brad Stevens has made a seamless transition from coach to general manager and has drafted well, which could help replenish the roster with cheaper, team-friendly contracts, but the Nuggets have tried the same and have shown it isn’t a guaranteed quick-fix. 

What’s unknown about the Celtics’ payroll is if incoming owner Bill Chisholm will change course once he takes control. Chisholm, a lifelong Celtics fan and Massachusetts native, is buying the team for $6 billion, but will keep current team governor Wyc Grousbeck in his position through the 2027–28 season. Chisholm recently secured the funding to secure the deal. Chisholm has said all the right things about extending the team’s title window, but he’s currently not footing the bill for it. 

My approach is to win and raise banners,” Chisholm previously told ESPN. “That’s in the near term and the long term. I’ve had a couple of sit-downs with Brad, and it’s been about aligning our goals and extending the window of this team. The plans that Wyc and Brad have laid out make perfect sense to me.”

Will Chisholm continue to let Grousbeck make decisions for the team at his own expense? It’s a question the Celtics might be faced with sooner than they were expecting. 

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

College Football’s Biggest Circus Descends on Baton Rouge

Lane Kiffin’s debut and the NFL eligibility battle are drawing national attention.

Cathy Engelbert Out As WNBA Commissioner After 2026

The controversial executive is retiring, the league said Friday.
Aug 25, 2017; Seattle, WA, USA; General overall view of Seattle Seahawks logo at CenturyLink Field during a NFL football game against the Kansas City Chiefs. Mandatory Credit: Kirby Lee-USA TODAY Sports
Exclusive

Mark Stevens Is Seahawks’ Top Minority Investor

Other investors joined the Seahawks’ new ownership from the Mittal-Grousbeck group.
podcast thumbnail mobile
Front Office Sports Today

9/4/26 – Judge Clears Pros for College, Good Good CEO Out, Russini Plots Comeback

0:00

Featured Today

Wild Transfer Window Shows How Premier League Towers Over Soccer

Spending in England vastly outstripped the rest of Europe.
September 3, 2026

Teams Are Spending Millions to Build Luxury Locker Rooms

It’s a recruiting pitch, a retention tool, and a seven-figure line item.
September 1, 2026

High School Football Sidelines Are Clogged With Content Creators

Administrators call these amateur newcomers the “pajama paparazzi.”
Aug 3, 2026; Washington, D.C., USA; Alexandra Eala (PHI) kisses the championship trophy during the trophy ceremony after her match against Jessica Pegula (USA) (not pictured) in the women's singles final of the 2026 Mubadala DC Open at Rock Creek Park Tennis Center. Mandatory Credit: Geoff Burke-Imagn Images
August 30, 2026

How Alex Eala Turned the Philippines Into a Tennis Nation

A December homecoming match could break tennis’s attendance record.
August 26, 2026

Deshaun Watson Has Done the Impossible: Unite Browns Fans

Watson was named the starter after complaining boos were “personal.”
Washington Redskins football shirts and a team flag on sale at a sporting goods store in Bailey's Crossroads, Virginia, U.S., June 24, 2020. REUTERS/Kevin Lamarque

Native Leaders to Commanders: Drop Old Name for Good

The franchise says there are no plans to revert to its old name.
September 2, 2026

Read the NBA’s Report on Clippers, Kawhi Leonard, and Aspiration

The league found the Clippers illegally went around the salary cap.
September 3, 2026

Clippers Sanctions Pair With Already Bleak Media Outlook

The team will likely be much harder to watch this season.
Sponsored

Kerri Walsh Jennings’s Playbook for the Future of Volleyball

The former gold medalist talks NCAA, the Olympics, & investing in volleyball.
September 1, 2026

Skylar Diggins Laments Chicago Sky’s Practice Facility Delay

Diggins said she expects to be with the Sky next season.
September 1, 2026

Stan Kroenke Has Deal to Buy Angels From Arte Moreno

The side announced the deal Tuesday.
First at FOS
August 31, 2026

Runners-Up Offered Seahawks Stake After Losing Out on Team

The deal is closing “very soon,” a source says.
August 31, 2026

Aaron Donald Return Supercharges Rams’ Status As 2026 ‘It’ Team

His return raised expectations and shortened betting odds.