The U.S. Open looked like fun and games for Racquet magazine.
The company threw a bustling rooftop party at Rockefeller Center with at least seven corporate sponsors, where guests juggled Shake Shack burgers with Ciroc goblets. They celebrated a new issue, guest-edited by David Granger, formerly of Esquire, with Andre Agassi on the cover — an A.I.-generated image of the champion wrapped absurdly in pastel pink feathers.
At the tournament, the magazine’s management mixed with current and potential business partners: Fila, Rolex, BNP Paribas, the Saudi Tennis Federation. A few weeks earlier, they played in and won a doubles tournament at a rarefied grass-court country club in Queens.
But behind those wins was a year of tumult and transformation, with the two co-founders locked in a dispute that led to dueling lawsuits.
In one corner was David Shaftel, the editor of the print magazine, who wanted Racquet to grow steadily and sustainably within its niche media lane. In the other was Caitlin Thompson, the publisher who wanted Racquet to “aggressively and ambitiously” expand into the increasingly big business of tennis, she said.
She saw merch collaborations and exuberant parties as a financial life raft for an unprofitable print product; she dreamed of opening branded tennis clubs all over the world with SoHo House-style membership plans.
In the battle for Racquet’s soul, the business side won. Ms. Thompson removed Mr. Shaftel from the company in November.
Their falling out was no secret. In a Defector story following Mr. Shaftel’s exit, he called Ms. Thompson’s vision “too grandiose and unrealistic” and said he “lost faith in her leadership.” She said she hoped “we can still figure out how to somehow work together.”
But the lawsuits they filed against each other this spring have, until now, played out in private. They reveal a deeper schism, with Mr. Shaftel referring to his co-founder in his complaint as an “unmitigated disaster,” who “plotted to oust” him. Ms. Thompson, in turn, accused Mr. Shaftel in court papers of stealing “confidential and proprietary information” to start a rival tennis magazine that “mimics” Racquet.
Beneath these accusations of contractual breaches was a fundamental difference in vision. Ms. Thompson’s ideas reflected a wider trend in media: Titles positioning themselves more as lifestyle brands than just content publishers.
Air Mail, an email newsletter, now operates a stylish boutique. So does Highsnobiety, winner of the National Magazine Award, which in fact considers itself more of an advertising agency. Legacy media also see the value in physical events; Vogue World, an international showcase for the magazine’s talent and advertisers, is accessible to anyone willing to buy a ticket. (In New York, prices ranged from $130 to $3,000.) Most magazines aren’t just magazines anymore.
“It’s not that hard to have a magazine if you don’t mind having a hobby, or you want to lose money,” said Ms. Thompson, who previously worked as a journalist for large media outlets, in an interview. “I didn’t leave the Washington Post or Time magazine or these other organizations to do an art project.”
From its first issue in 2016, funded by $55,000 from Kickstarter, Racquet has offered a cultural view of the tennis world. Published quarterly, the 120-or-so-page editions were packed with essays from well-known writers on art and fashion — and packaged stylishly enough to be displayed on a coffee table.
Racquet invited tennis fans (and the tennis curious) into a world where players shared their obsessions — as when Naomi Osaka’s guest-edited issue included an article about sports manga and a conversation between musician Dev Hynes and painter Takashi Murakami.
Today the magazine publishes less frequently, around three times per year, and circulation is typically around 5,000. It is financed primarily by creative agency services; Racquet lends its sensibility to other companies by collaborating on merch (like a $2,400 watch with Maurice de Mauriac) or events (like an Evian party that had Maria Sharapova playing tennis on a sightseeing boat). When Gucci paid Racquet to photograph its new collection of tennis clothing, the Italians’ budget financed most of the issue. Photos from that shoot appeared on the front and back covers.
“That’s the Tyler Brûlé model to a T,” said Ms. Thompson, referring to the famed founder of Monocle, a pioneer of blurring editorial and advertising. Mr. Brûlé is an inspirational figure to Ms. Thompson, 44, who pingpongs between coming across as a media wonk and as a competitive athlete. “A nerd-jock,” as she put it, who played Division 1 tennis in college while studying magazine journalism. She wears tennis skirts to work and counts powerful editors among her mentors and friends. (“She just has a desire to get stuff done,” said Radhika Jones of Vanity Fair.)
In October, the Racquet team will shoot a campaign in Portofino, Italy, for Sease, a sportswear brand from the Loro Piana family. The fee is “mid-five figures,” said Ms. Thompson, who will compete in the brand’s friends-and-family tennis tournament. Racquet is also actively bidding on a space for its own permanent indoor court in New York, around which it would host events and build offices and a multimedia studio.
It is even expanding into Korea through its first international licensing agreement, aiming to bring more young recreational players (“Korean tennis hipsters,” as Ms. Thompson said) into the professional world.
“My goal is bigger than a media company — my goal has been to impact the sport,” she said, with some defensive swagger. “I won’t apologize for wanting to do something bigger.”
The Gucci-fronted issue, which sold all 5,000 copies, priced at $30 each, was Racquet’s first edition since Mr. Shaftel was removed from the company in November. In May, he sued Racquet in New York for breach of contract.
According to Mr. Shaftel’s complaint, Ms. Thompson removed him through a “disparagement campaign,” convincing a majority of investors, or preferred shareholders, to vote in favor of her solo leadership. Mr. Shaftel’s suit also alleged the “wrongful confiscation and conversion” of his shares. He said he had been paid just $400 for one-third of the company.
Mr. Shaftel painted Ms. Thompson’s management as “incompetent” and “overly-ambitious” in his complaint.
The partners’ troubles escalated in May 2023, after Ms. Thompson overspent on a French Open event by $250,000, according to Mr. Shaftel’s suit. (The loss resulted from her receiving oral but not signed contractual agreements from sponsors.) It happened again three months later, during the U.S. Open, said Mr. Shaftel’s complaint.
In June, Ms. Thompson responded with a countersuit. It accused Mr. Shaftel of breaching noncompete, non-solicitation and confidentiality agreements. The complaint alleged that he had disparaged Racquet by speaking to Defector — comments that resulted in Racquet losing a television deal, among other potential partnerships.
“It is true that we had a different vision for how to grow the business,” Mr. Shaftel told The Times.
He has since founded another tennis and culture publication, The Second Serve, after leaving Racquet. “I’m running the company that I want to run, and she’s running the one that she wants to run,” he said.
The Second Serve’s core strategy is editorial. It is a newsletter and “an independent tennis magazine, not a tech start-up,” Mr. Shaftel said. (The magazine, Open Tennis, is published in print semiannually, with an emphasis on photography.) “Taking on those ancillary projects and lines of business is great, as long as they’re subservient to your core strategy.”
Mr. Shaftel was a well-liked editor, and some Racquet contributors followed him to The Second Serve. They included journalists Ben Rothenberg, a former freelance writer for The New York Times, and Giri Nathan, a Defector co-founder who had written Racquet’s popular newsletter.
In her lawsuit, Ms. Thompson accused Mr. Shaftel of stealing Racquet’s newsletter subscriber list “to boost his competing business.” The complaint claimed that some Racquet subscribers received an unsolicited email in January. The subject line: “Welcome to The Second Serve.” Mr. Shaftel declined to comment on the suit, citing active litigation.
The pair said they’re eager to settle their lawsuits and expect to do so this month. Ms. Thompson said she doesn’t mind Racquet having competition: “You want your opponent to show up and play well so you can play better,” she said.
But moving on from the split hasn’t been entirely smooth.
Racquet and Mr. Rothenberg, its former contributor, were sued in Germany for a 2020 investigation he published about Alexander Zverev, now the world No. 2 player. The magazine was later dropped from the case amid confusion in the serving process.
Around that time, Racquet ended its support for Mr. Rothenberg’s legal defense, leaving him to pay some of his own bills. Ms. Thompson has said it was because of public comments Mr. Rothenberg made about Mr. Zverev that went beyond what the article included.
“That’s nothing she ever said to me,” said Mr. Rothenberg, who believes Racquet stopped supporting him primarily because he began writing for The Second Serve. He pointed to the timing of Ms. Thompson informing lawyers of her decision: one day after his first byline appeared.
Ms. Thompson remains starry-eyed about magazines, despite the fracas. She wrote her college thesis on Esquire, and persuaded Mr. Granger to edit Racquet’s 25th’s issue. It was his first return to substantial magazine editing since he was fired from Esquire in 2016.
“Nothing recreates what magazines used to be able to do,” Mr. Granger said. “I think it’s an ambitious, beautiful outlet for people who actually love the sport.”
Ms. Thompson does love tennis — even if she once hated it. After her final match in college, she said, she simply walked off the court, leaving all of her gear behind.
She had learned to play as a child with her grandmother on dusty suburban Arizona courts.
Years later, she returned to the game on New York City’s cracked public courts, which became her meeting grounds for future business associates, including Steph Chung, who formally joined Racquet as managing partner in November, after a career in finance and mergers and acquisitions.
“The brand itself was so powerful,” said Ms. Chung, who helped ink a deal with NBC for a Racquet-hosted podcast this summer about the French Open and the Paris Olympics. “It was just not having the right discipline in deal negotiations and contracts.”
Last year, the company broke even, Ms. Chung and Ms. Thompson said. This year, they expect to be profitable. If so, it will be for the first time.
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