Friday, May 22, 2026

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

Charlie Pilner and Nikolas Rohrmann

How 2 Brown Undergrads Became Sports Deal Brokers

An experimental project turned into a permanent course and business deal network.

Fever Get Warning, No Fine Over Caitlin Clark Injury Report

A WNBA source confirmed that they were not fined.
Dec 21, 2024; Austin, Texas, USA; A view of the CFP logo and SEC logo before the game between the Texas Longhorns and the Clemson Tigers in the CFP National Playoff First Round at Darrell K Royal-Texas Memorial Stadium. Mandatory Credit: Jerome Miron-Imagn Images

SEC Holds Cards to 24-Team College Football Playoff

CFP expansion will be a major topic at the SEC spring meetings.
U.S. Senator Richard Blumenthal (D-CT) speaks with the press after the Republican-controlled U.S. House of Representatives passed bipartisan legislation to fund Department of Homeland Security agencies including the Secret Service and Transportation Security Administration in a move to end the partial shutdown that has gripped their operations for nearly 11 weeks, on Capitol Hill in Washington, D.C., U.S., April 30, 2026.

Critics Warn Kalshi and Polymarket Risk a Juul-Style Reckoning

Their advertising methods came under fire from lawmakers this week.

Featured Today

NFL Rivalries Are Made on the Field, Mocked in Schedule Release Videos

Every year, teams find new ways to one-up themselves (and their rivals).
Bart Swings/Falyn Fonoimoana/Avery Poppinga
May 14, 2026

OnlyFans Is Paying Pro Athletes What Their Sports Won’t

The adult-content platform is a reliable income source for niche athletes.
May 13, 2026

How Sports Graphic Designers Are Grappling With the Rise of AI Art

The release of ChatGPT 2.0 Images sparked a conversation among sports designers.
May 12, 2026

Collectible Cups Are Sending Sports Fans Into a Frenzy

The drink is secondary to the wild vessel it comes in.
Nov 20, 2025; Salt Lake City, Utah, USA; Vegas Golden Knights head coach Bruce Cassidy watches play against the Utah Mammoth during the third period at Delta Center

NHL Coaches’ Association Pushes Back on Vegas Cassidy Restrictions

Vegas is within bounds, but the move is unusual and controversial.
May 19, 2026

Arsenal Wins First Premier League Title Under American Owners

The Gunners hadn’t won England’s top league since 2004.
May 19, 2026

Trail Blazers Lay Off Dozens As Tom Dundon’s Cuts Continue

The team confirmed the departures in a statement Tuesday.
Sponsored

Mark Cuban Peels Back the Curtain

Mark Cuban discusses sports ownership, the rise of NIL, and the evolving media landscape.
May 4, 2026; New York, New York, USA; New York Knicks guard Josh Hart (3) controls the ball against Philadelphia 76ers forward/guard Kelly Oubre Jr. (9) during the first quarter of game one of the eastern conference semifinal round of the 2026 NBA Playoffs at Madison Square Garden.
May 18, 2026

Knicks Ticket Demand Sees MSG Get-In Prices Soar

Resale ticket prices for any potential Finals games at MSG begin at about $2,500.
May 13, 2006; Washington, D.C, USA; FILE PHOTO; Houston Comets at Washington Mystics -- Houston forward Sheryl Swoopes brings the ball up court.
May 14, 2026

Houston WNBA Team Expects to Keep Comets Name

The Connecticut Sun will move to Houston in 2027.
May 13, 2026

Bob Myers Will Run Sixers While Leading Hunt for New GM

Myers constructed four championship teams in Golden State. 
May 11, 2026

Braves Earnings Show Promise and Pressure of RSN Shift

The club’s revenue surged, aided in part by the earlier season start.