As the FTX cryptocurrency exchange imploded last fall, Tom Brady, the seven-time Super Bowl-winning quarterback, made an urgent phone call.

He called Sina Nader, FTX’s head of partnerships. The exchange’s staff was in the middle of a crisis meeting with its beleaguered founder, Sam Bankman-Fried. Mr. Nader could not answer. “I would never expect to turn down a call from Tom Brady,” he said.

Mr. Brady had reasons to worry. As an “ambassador” for FTX, he appeared at the company’s conference in the Bahamas and on television. commercials that promoted the exchange as “the most reliable” institution in the loosely regulated world of crypto.

His money was also at stake. As part of an support deal that Mr. Brady signed in 2021, FTX paid him $30 million, a deal that consisted almost entirely of FTX stock, three people familiar with the contract said. Mr. Brady’s wife at the time, the supermodel Gisele Bündchen, received $18 million in FTX stock, one of the people said.

Now FTX is bankrupt, and Mr. Bankman-Fried is facing criminal fraud charges. Mr. Brady, 45, and Ms. Bündchen, 42, were sued by a group of FTX customers seeking compensation from the celebrities who endorsed the exchange. On top of all that, the terms of the deal would require the former couple, who divorced last year, to pay taxes on at least some of their now-worthless FTX stock, said two people familiar with the support agreement.

Their situation is the most high-profile example of a humiliating reckoning facing the actors, athletes and other celebrities who have rushed to embrace the easy money and online hype of cryptocurrencies. During the boom times, Paris Hilton, Snoop Dogg, Reese Witherspoon and Matt Damon all splurged or invested in crypto projects, bringing a mainstream audience to the confusing world of digital currencies. It was fun – and profitable – as prices soared.

But last year’s crash ended the celebrity crypto bonanza.

In October, the Securities and Exchange Commission ordered Kim Kardashian to pay $1.26 million for failing to make proper disclosures when she approved the EthereumMax crypto token. In December, a lawyer in California sued two crypto companies, MoonPay and Yuga Labs, accusing them of using a “vast network of A-list musicians, athletes and celebrity clients” to defraud investors about digital assets.

In March, the SEC charged actress Lindsay Lohan, internet influencer Jake Paul and musicians including Soulja Boy and Lil Yachty for illegally promoting crypto assets. And at the end of May, after months of failed attempts, process server provided court documents to Shaquille O’Neal, the retired basketball star who was sued for promoting FTX, according to legal filings. Mr. O’Neal was served while broadcasting a National Basketball Association playoff game.

Representatives for Mr. Brady, Mr. Bankman-Fried and MoonPay declined to comment. A spokesperson for Yuga Labs said the company “has never paid a celebrity to join the club.” Representatives for Ms. Bündchen and Mr. O’Neal did not respond to requests for comment.

Tech startups and celebrities have long had a symbiotic relationship. The startups offer stars a way to make money while staying at the forefront of internet culture; the celebrities help young companies gain credibility and reach a larger audience.

Of all the startups that have recruited celebrities to endorse crypto, FTX may have been the most eager. As Mr. Bankman-Fried tried to turn FTX into a household name, he made a list of celebrities he could envision promoting the company, Mr. Nader, the former FTX executive, recalled. Mr. Brady’s name was at the top.

A former college football player, Mr. Nader was in charge of recruiting Mr. Brady and other stars. In June 2021, Mr. Brady and Ms. Bündchen agreed to a deal with Mr. Bankman-Fried, praising the “revolutionary FTX team.” Mr. Brady seemed genuinely interested in crypto, Mr. Nader said, and occasionally had conversations with Mr. Bankman-Fried.

“Imagine a tiger and a lion talking,” Mr. Nader said. “They’re a little bit different, they do different things, but they’re really formidable in their own arenas.”

In 2021, Mr. Brady also co-founded Autograph, which helps famous people sell the crypto collectibles known as non-fungible tokens, or NFTs. Autograph raised more than $200 million from investors, and Mr. Bankman-Fried joined the board.

That same year, Mr. Brady and Ms. Bündchen starring in a $20 million advertising campaign for FTX, with commercials that ran during NFL games. Mr. Brady also posted TikTok videos with Mr. Bankman-Fried from FTX headquarters in the Bahamas, where he spoke at a conference hundreds ago. Backstage, Mr. Bankman-Fried remarked that he could imagine buying a football team someday with Mr. Brady. Ms. Bündchen also appeared at the conference as FTX’s head of environmental and social initiatives.

When FTX collapsed last November, the company’s $32 billion valuation — including Mr. Brady and Ms. Bündchen’s 48 million shares — plummeted to zero. The pair also received a small amount of Ethereum, Bitcoin and Solana tokens to trade on the platform, one of the people said, which disappeared in the FTX bankruptcy.

Mr. Brady has not commented publicly on FTX or his relationship with Mr. Bankman-Fried. After the FTX emergency meeting in November, Mr. Nader called him back.

“He was worried,” Mr. Nader said. “The first thing he asked me was, ‘Sina, how are you doing? I know you put your heart and soul into this.'”

Ms Bündchen said in March an interview with Vanity Fair that she “believed the hype” and felt “blindsided.”

Mr. Brady’s other crypto venture also struggled. Autograph’s revenue slumped last year amid the crypto meltdown, a person familiar with its finances said. The startup has shifted its strategy to focus more on helping celebrities find ways to foster loyalty with their fans, and less on marketing crypto tokens to consumers, the person said. The company also removed some crypto language from its marketing, dropping terms like NFT, another person with knowledge of the company said.

Autograph also cut more than 50 employees in layoff rounds, a third person said. The reductions were reported earlier by Insider. An Autograph spokeswoman declined to comment.

Mr. Brady also ran into legal trouble. In December, Adam Moskowitz and the law firm Boies Schiller Flexner filed a lawsuit in federal court in Florida accusing him and Ms. Bündchen of misleading investors. Among the other defendants are comedian Larry David, NBA star Steph Curry and tennis player Naomi Osaka, all of whom supported FTX.

“None of these defendants performed any due diligence prior to marketing these FTX products to the public,” the lawsuit said.

Some celebrities narrowly escaped the crypto mess. Katy Perry, the pop star, talked about a partnership with FTX that never materialized, three people familiar with the situation said.

In the spring of last year, Taylor Swift discussed a deal with FTX that could have paid as much as $100 million, two people familiar with the matter said. A tour sponsorship was on the table after Ms. Swift rejected other promotional options, a person with knowledge of the talks said. The size of the agreement was reported earlier by The Financial Times.

Mr. Moskowitz, the lawyer suing the celebrities, said in a podcast in April that Ms. Swift had done due diligence on FTX, asking the exchange to prove that its cryptocurrencies were not unregistered securities. His comments caused a flurry of headlines about Mrs. Swift’s business acumen. But in an interview with The New York Times, Mr. Moskowitz said he had no inside information on the talks.

In fact, Ms. Swift’s side signed the sponsorship deal with FTX after more than six months of discussions, three people familiar with the deal said, and it was Mr. Bankman-Fried who pulled out. The last-minute reversal left Ms. Swift’s team frustrated and disappointed, two of the people said.

A spokeswoman for Ms. Swift declined to comment.

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