When I asked Jide Zeitlin late last year about a 10-year-old article accusing him of using “deception to lure a woman into an unwanted romantic relationship,” his denial was absolute. “It’s not true,” Zeitlin stated. “OK? That’s on the record. It’s not true.”

Zeitlin, then the CEO of Tapestry — parent company of luxury brands such as Coach, Kate Spade and Stuart Weitzman — went so far as to urge me to dig into his background. “I’m pretty certain you’re not going to find any paper trail on me playing those kinds of games,” Zeitlin said.

Tapestry’s communications chief, Andrea Resnick, was even more adamant when I raised the question again in January. She accused me of advancing a “racist agenda” (Zeitlin is Black) and “using your personal credibility … to give a despicable hatchet job new life.” As recently as this month, a law firm hired by Zeitlin threatened to sue if such allegations were published.

On Tuesday, the company announced Zeitlin had resigned “for personal reasons,” only four months after it had extended his contract for three years. Zeitlin issued a statement to The Wall Street Journal that said, “In the past month, a woman I photographed and had a relationship with more than 10 years ago reached out to various media organizations to express her concerns about what had occurred. … I felt compelled to resign today because I do not want to create a distraction for Tapestry, a company I care deeply about.” (Later in the day, Zeitlin published a post on LinkedIn in which he acknowledged he “drew too close” to the woman but asserted, “I did not use power, wealth, or position to further that relationship.”)

Zeitlin resigned after Tapestry launched an investigation last week into the CEO’s conduct. The company hired the law firm Fried, Frank, Harris, Shriver & Jacobson to handle the inquiry, which appears to have been prompted by 60 questions I sent the company on June 23 for this article. Zeitlin was allowed to resign, rather than be fired, and received no severance payment.

The resignation represented a calamitous fall for Zeitlin, 56, one that was nearly as improbable as his rise. Born in Nigeria, the son of a maid, Zeitlin was largely brought up by an American family (which eventually became his legal guardian) and rose to become a rare Black partner at Goldman Sachs before eventually becoming one of only five Black CEOs among Fortune 500 companies.

Zeitlin enjoyed a gilded reputation. His partnership at Goldman Sachs earned him more than $100 million when the firm went public and placed him in the financial elite. And Tapestry thrived during his brief tenure as CEO, at least until the pandemic ravaged the business. “What stood out was the thoughtful assessment, new initiatives, methodical approach, and proactive tone from new CEO Jide Zeitlin,” a research analyst at Evercore ISI wrote in February.

Recently, Zeitlin’s star had risen even higher as he propelled himself into the national conversation on race. Zeitlin’s fearless embrace of the Black Lives Matter movement had an authenticity and depth few corporate executives can muster. On June 1, he posted a moving essay on LinkedIn, addressing George Floyd’s killing and the looting that had occurred at a number of Tapestry retail stores. “We can replace our windows and handbags,” he wrote, “but we cannot bring back George Floyd, Ahmaud Arbery, Breonna Taylor, Eric Garner, Trayvon Martin, Emmett Till, and too many others. Each of these black lives matter.”

The essay became a sensation, and it made Zeitlin a leading corporate voice for social change. He spoke about the movement in a June 3 appearance on ABC’s “Good Morning America,” and then on June 21, he was on CBS’ “Face The Nation.”

Yet for all of Zeitlin’s accomplishments, there were troubling episodes in his past. Perhaps most surprising, many of the facts were out in the open to an extent that raises the question of how closely, if at all, Tapestry’s board of directors vetted its CEO before appointing him last year. The company didn’t respond when asked how it had missed information, some of it available in a simple Google search.

Some problems seemed like benign business stumbles: For example, a company that he ran in India went bankrupt. But then there was what appeared to be almost a past second life for Zeitlin. Working under an alias, he took photos, many sexual, at least some involving nudity, of women in a studio just feet from where his wife and children lived. He had what he now acknowledges was an “inappropriate relationship” with one of the women he photographed. That life had surfaced in 2009, hindering a chance for him to enter government service, only to be publicly left behind — until today.

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Stirred by Zeitlin’s remarkable rise — he had added the CEO title at Tapestry in September 2019 after previously being its chairman — I approached the digital newsletter Air Mail last fall with the idea of writing a profile of him. The publication commissioned the article, and Zeitlin agreed to be interviewed.

His was a tale worth telling. Since the day he was born to a single mother in sub-Saharan Africa, Zeitlin’s life has been something bordering on the incredible. “You have to get lucky, and I’ve been unbelievably lucky,” he told me during an interview last November at Tapestry’s headquarters at Hudson Yards, the new development on Manhattan’s West Side.

As Zeitlin told it, his path to Tapestry’s corner office began in Ibadan, Nigeria’s third-largest city, where he was born. When he was a baby, his mother sent him to live with relatives in the countryside while she worked as a domestic for foreign families in Lagos, then the country’s capital.

Among those were the Zeitlins, an American family. Arnold Zeitlin was a veteran foreign correspondent for The Associated Press. He and his wife had two young children and when Olajide, or Jide as he was known, would visit his mother at their house, he’d play with one of the family’s daughters. The Zeitlins, thinking Jide would get a better education in Lagos, suggested he live with them, an arrangement his mother embraced. “She was an amazing mother who just didn’t have a lot of resources,” Zeitlin told Forbes Africa in 2012.

When the Zeitlins moved to Pakistan in 1970, they asked Jide, who was 5, if he would like to join the family and move there. Jide said yes. And for the second time, Jide’s mother agreed to let him go. Eventually, the Zeitlins would become his legal guardians, and he took their last name.

“My Nigerian mother gave away her eldest son so that he might have a better life,” Zeitlin said in a 2014 speech. “I cannot imagine giving away any of my three children.” (His mother would later move to London to work in the home of a promising Ghanaian diplomat named Kofi Annan, before he became secretary general of the United Nations. In 2008, she died in a car accident.)

After Pakistan, the Zeitlins were posted to the Philippines but were forced to leave the country in 1975 when Arnold Zeitlin wrote articles that angered its president, Ferdinand Marcos, and his wife, Imelda. From Manila, they moved to Cambridge, Massachusetts, where the Zeitlins sent him to Milton Academy, a prep school. After that, Zeitlin was off to Amherst College, where he studied English and economics. There he got the Wall Street bug. He wrote to a number of investment banks, seeking an internship. They all turned him down.

A fortuitous meeting with a partner at Goldman Sachs led to a summer internship. He went back every summer, including after his first year at Harvard, where he had gone to get his MBA. When he graduated from Harvard in 1987, Goldman offered him a job in its world-beating mergers and acquisitions department.

Within weeks of his arrival, Zeitlin got another huge break when he became the protégé of Hank Paulson, who was then running Goldman’s Chicago office and en route to becoming its CEO in 1999 and secretary of the Treasury in 2006. In 1996, Goldman named Zeitlin a partner. When the firm completed its own initial public offering in May 1999, his .325% ownership stake was worth $117 million after the first day of trading.

One of Paulson’s top clients was the Sara Lee Corp. Sara Lee also owned Coach, a high-end leather goods maker. Zeitlin helped Coach execute a successful IPO in 2000, impressing then-CEO Lew Frankfort in the process. By 2005, Zeitlin had been invited to join Coach’s board.

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Zeitlin’s ties to Paulson helped him mightily. In 2004, Zeitlin said, Paulson asked him to go to India and figure out a strategy for the firm there. While there, Zeitlin spotted a new opportunity: cellphone towers. At the end of 2005, he formed The Keffi Group, a private investment firm, to do deals, including buying cell towers in India.

Zeitlin soon experienced his first stumbles. In January 2009, a $62.5 million investment in a medical startup went south when the company filed for bankruptcy. Later that year, Zeitlin’s Indian cell tower business, Independent Mobile Infrastructure Ltd., also filed for bankruptcy.

For others, such setbacks might have taken years to recover from. Zeitlin, by contrast, was ready to tackle a new challenge.

Thanks to “a friend of a friend” from his days at Amherst, according to Zeitlin, he was asked to join Barack Obama’s economic transition team and then offered a job at the Treasury Department. Paulson told him to take it, but Zeitlin decided not to, in part, he said, because it was in Washington and his young family was in New York City. Paulson had a different memory, according to an email he provided for this article. Paulson said Zeitlin had done “an excellent job” as a young banker working on Sara Lee. “As far as I know, there were never any complaints about inappropriate behavior by Jide when he was at Goldman Sachs and he left the firm with a good reputation,” Paulson’s email continued. “Jide approached me and said he was seeking a senior job at the Obama Treasury Department and wanted advice and a recommendation. I told him it would be better to start at a lower level. I also asked him about some unseemly rumors I had heard [unrelated to Goldman Sachs] and he denied them. When I discussed him with Treasury I said he was talented but his personal conduct should be looked into.” (Zeitlin lawyers denied any unseemly behavior at Goldman. The firm’s communications chief, Jake Siewert, declined to comment.)

Still, six months later, another government opportunity presented itself. According to Zeitlin, the head of White House personnel asked him to be the U.S. point man on financial reform at the United Nations in New York. He met with Susan Rice, Obama’s U.S. ambassador to the U.N., and came away impressed. On Sept. 24, 2009, Obama nominated Zeitlin for the post of U.S. ambassador for U.N. management and reform.

Zeitlin was about to learn, however, that in the pressure cooker of Washington, your mistakes often mattered more than your triumphs. And Zeitlin’s mistakes were nowhere near as buried as he had thought.

On Nov. 4, 2009, the morning of his Senate confirmation hearing, The Washington Post published an article about Zeitlin’s problems in India. Zeitlin chalked it up to the usual political sparring over nominees that occurs in Washington prior to confirmation hearings. “That’s what’s called ‘Washington theater,’” Zeitlin told me in one of our interviews.

During the hearing itself, with Zeitlin’s family in attendance, he parried questions about the Post’s article from Democratic Sen. Robert Menendez and from Republican Sen. Richard Lugar. “It’s important to me, clearly, to address the issues raised in the article,” Zeitlin said under oath, “and to underscore the fact that, although no one bats one thousand, I have an exceptionally strong investment and financial track record over the last 25 years, and during the last several years.” On Dec. 8, the Senate Foreign Relations Committee recommended that the Senate approve Zeitlin’s nomination. It seemed he was poised for the next rung on the ladder.

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Zeitlin’s testimony was not sitting well with Gretchen Raymond, a 38-year-old mother of two in Stamford, Connecticut, then working as a private chef for a billionaire in nearby Greenwich. Raymond had met Zeitlin two years earlier, in January 2007.

On Dec. 9, 2009, the day after his confirmation hearing, Raymond emailed Max Gigle, then a staff assistant to Connecticut Sen. Chris Dodd, an influential member of the Senate Foreign Relations Committee. “This man has put me and my family through hell,” she wrote of Zeitlin. (Gigle said he has no memory of the interaction.)

In her email, Raymond recounted how she met Zeitlin after answering an ad placed on Craigslist, with the headline “Fit yes, experience not necessary,” by a man named James Greene, who said he was a fashion photographer working out of “Sohophoto.” At the time, Raymond was working as a fitness model and needed some photos of herself. After talking with Greene on the phone, she agreed to meet him “for a fitness shoot” at a gym.

In the several weeks before Raymond and Greene agreed to meet for the photo session, there were emails between them focused on what she should wear and what parts of her body he planned to focus on; she also shared other photos of herself. On Jan. 6, 2007, Greene emailed Raymond and thanked her for her photographs: “Now have a lot more to think about,” he wrote. “One of the shots you suggested is of your ass while you are working out with leg weights. As I am trying to envision this, I was hoping that you had some existing shots of your ass. The only shot you sent of your butt is the one in jeans — but the jeans are so busy (the pockets, the stitching, etc..) it’s hard to see you. Do you have any other shots of your butt? A lot of times runners in particular have hard butts, but not much in the way of contours, suspense or drama (in their butts, not their personality).”

In an email on Jan. 12, 2007, Greene also made what he acknowledged was an unusual request: “Please remember not to wear panties or a bra when you come into the city on Monday…” Greene explained that he didn’t want her underwear to interfere with the clothes she wore during the shoot.

On Jan. 15, 2007, Raymond agreed to meet Greene. “Get a good night’s sleep,” he wrote. As if to emphasize that he worked differently than other photographers, Greene had informed her that he used a Hasselblad medium format camera and old-fashioned film. “I tend to shoot very deliberately,” he wrote. “In other words, one shot at a time rather than just pushing the autowind and hoping to get lucky.” She arrived at the photo shoot with her make-up artist Rita Madison, her workout clothes, fishnet stockings with straps and “boy shorts.” The photo shoot went well — although Greene later told Raymond all the photographs he took were lost — and late that night Greene wrote her an email:

“I am about to go to bed and am hoping that I do not wake up at 3:00 a.m. again. Given our day today, however, there is a real risk that I will wake up in the middle of the night with thoughts of you swirling around in my head.” He extolled her “breathtaking beauty and naturalness” and worried someone would take advantage of her openness or desire for recognition. “I know that you read people well and are careful, but please please be doubly careful as you get deeper into this business. There are a lot of remarkably smooth types who make it their business to take advantage of others. (Sorry for my paternalistic lecture.) … I have a thousand questions I would love to ask you over a cup of coffee one day. … Thanks for being so generous with your time today and being so pleasant. I look forward to seeing you again — soon.”

Over the course of the next few months, according to Raymond, she and Greene became friends, then lovers. Their first post-photo shoot meeting was at the NoHo Star restaurant, she said; he was leaving for a Canadian dog sledding trip that day. “We met, spoke and I remember it as a nice connection,” Raymond told me. “When he was gone on his trip, I texted him that I felt a real void without his messages. When he called me from the home that he stayed in after, he told me that he had been thinking of me the entire time and he just loved my text.”

Soon after, Greene confessed to her that he had been living a double life. His real name was Jide Zeitlin. She had become suspicious of him. “It was becoming very clear to me he was not a photographer,” she recalled. “I said, ‘I want to know your real name because I want to Google you.’ He laughed and said, OK, I am James Zeitalin.’ I had him spell it and wrote it down.” The next day, she Googled that name and up popped a picture of Jide Zeitlin.

As Raymond wrote in her letter to Gigle, the Senate aide: “About one month into our friendship (approximately Feb. 24, 2007.) I discovered his true identity. He told me that he wanted to work on his photography and didn’t feel that I would have worked with him if I knew he was not a professional and he just wanted to meet me. He apologized for the deception and told me he was falling in love with me. With great regret I began a romantic relationship with Jide.”

At the time, Zeitlin’s wife, Tina Goldberg, was pregnant. Goldberg, who is also a Goldman M&A department alum, works in the upper reaches of the fashion industry, as the chief commercial officer at Anne Klein International. (Goldberg did not immediately reply to an email seeking comment.)

Their consensual affair lasted until October 2007, according to Raymond. “I was under the impression that he was deeply in love with me and planning a future with me,” she wrote Gigle.

Their affair, Raymond said, ended because Zeitlin told her that he had too much on his plate and needed to “figure out our life.” She was devastated. “I was absolutely heartbroken,” she said.

A month after Zeitlin ended their affair, Raymond’s husband intercepted a text from Zeitlin wishing her a happy Thanksgiving. Furious, her husband called Zeitlin’s wife and told her about the affair. Gretchen Raymond then emailed Zeitlin’s wife; contemporaneous emails between the two women, which I’ve read, make clear this was not a pleasant conversation.

Things would turn uglier still. “One week later someone came to my home and threw a construction brick through my Durango,” Raymond wrote in her letter to the Senate. When the police came, she said they told her, “Somebody is sending you a message.” (Raymond filed a complaint about the incident with the Stamford Police Department; there’s no sign the police took any action.)

Working together, Raymond and her husband began to uncover details about Zeitlin’s photographic work. They learned that Raymond was not the only person Zeitlin photographed. They began to fill in the picture of how he operated. (Neither Zeitlin nor Tapestry responded to extensive written questions about these activities.)

To solicit models, Raymond said, Zeitlin used the same [email protected] address he used to respond to her initial email in December 2006. And Raymond said that Zeitlin’s “Sohophoto studio” was the apartment he had purchased adjacent to his family’s residence on the sixth floor of a Greene Street apartment building in Manhattan’s tony SoHo neighborhood. (Zeitlin later tried to sell the two apartments.) She said Zeitlin took her to the photo studio “at the top of the winding staircase” on the same day as their second NoHo Star meeting. “I had no idea at the time though that his wife and child were right next door,” she said.

Raymond and her husband undertook a two-person detective quest to try to uncover how many women Zeitlin had photographed. Obsessively cross-referencing a modelling-website i.d. that Zeitlin had sent along with the [email protected] email address and other details, and matching some of the photos with visual elements from different pictures (Raymond said she recognized some details as the same studio she had been photographed in), she and her husband identified a series of photos of young women they believed Zeitlin had taken and posted on sites like Model Mayhem and OneModelPlace. (Zeitlin removed his profile on these sites sometime in 2008, according to Raymond.)

All told, Raymond found seven models they believed Zeitlin had photographed, nearly all of them in demonstrably sexual poses, many lying on a bed in skimpy lingerie. Some involved nudity.

One woman, Tamara Williams, confirmed in an email that she had been photographed by a man she knew as “Greene.” She said she was over 18 when she was photographed topless on a bed in Zeitlin’s SoHo studio around 2005, “but nothing bad transpired.” Williams declined to elaborate on her experience.

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In the winter and spring of 2008, in a bid to expose Zeitlin’s hidden life, Raymond contacted a series of FBI agents. To her frustration, however, she was unable to get any traction. She reached out to the FBI again in September 2019 after Zeitlin became Tapestry’s CEO, again without any success. (The FBI office in New Haven, Connecticut, that Raymond contacted did not respond to requests for comment.)

One connection that appeared promising in 2009 was Wall Street Journal reporter Peter Lattman, who had written about the cellphone tower business for the publication. But after Raymond’s husband asked her to stop, she broke off contact with Lattman. Lattman, now overseeing The Atlantic and other media investments for the Emerson Collective (which donates to ProPublica), acknowledged having numerous conversations with Raymond. He said he found her story credible and confirmed in emails to Raymond that I have seen that Zeitlin had used the website onemodelplace.com.

Finally, in December 2009, Raymond struck some pay dirt when Josh Rogin, a reporter at The Cable — a blog of Foreign Policy magazine — became interested in her claims about Zeitlin after she emailed him out of the blue.

A few weeks after Rogin began making calls, he got a tip from Tommy Vietor, then an assistant White House press secretary, that the Obama administration had decided to drop Zeitlin’s nomination. In late December 2009, Rogin broke the news: Zeitlin’s nomination had been withdrawn after “rumors swirled” about his “overall character” and “elements of identity fraud.” Zeitlin was allowed to say he withdrew his nomination for “personal reasons.” (In an email, Vietor, now the co-host of “Pod Save America,” wrote that he has no idea who Zeitlin is; Rogin, now a Washington Post columnist, declined to comment.)

Zeitlin returned to The Keffi Group, remained on the board of Coach (where he became chairman in November 2014) and continued to serve on the board of Amherst College, where he had assumed the chairmanship of the board of trustees in July 2005. In 2014, Amherst gave him an honorary doctorate. In his address, he spoke of his life and experiences. He thanked his wife and three children, adding, “you have trusted me beyond reason and loved me no matter how idiotic I’ve been.”

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Zeitlin was alternately evasive or dismissive last November when I asked basic questions about the events leading up to his sudden withdrawal from the United Nations job in 2009. “Washington is a very different world than Wall Street,” he said, presenting the vitriol hurled his way as an eye-opener. “If you’re sitting in New York, it feels as though it’s very personal. If you’re sitting in Washington, it’s just another day at the office.” That did not seem to mesh with his background (and success) at Goldman Sachs, a place that, like Washington, can be plenty rough and tumble.

Moreover, the allegation — reported by Rogin in 2009 — that Zeitlin “used deception to lure a woman into an unwanted romantic relationship” seemed all the more sensitive. As Zeitlin told me, “Particularly since I’m the CEO of an organization that is 79% women that cares immensely about inclusion, it feels like it’s a gratuitous shot that doesn’t necessarily add up.”

Zeitlin denied everything. He insisted I had “missed” the part of Zeitlin’s Senate confirmation hearing where he was asked about this relationship. (The video record of his confirmation hearing remains available on the Senate Foreign Relations Committee’s website, but nothing in the hourlong session remotely addressed Raymond or her claims.)

Zeitlin also said he had never “consummated” any relationship with Raymond. “I suspect that I’m one of the few people who has been accused of not consummating a relationship,” he said.

He was just getting started. Zeitlin said political enemies that had been looking to derail his nomination created a lie about him luring a woman into an unwanted relationship. “There is no substance” to the charge, Zeitlin said. “Let’s just be 100% clear [about that].” He repeatedly suggested he was collateral damage in a GOP plot to wound Obama’s foreign policy team.

To buttress his claims of having done nothing untoward, Zeitlin pointed to discussions he said he had in 2015 with people close to then-Treasury Secretary Jack Lew about taking a role — six years after he withdrew his U.N. nomination — as undersecretary of the Treasury. “There’s not a chance” the Obama administration would have come back to him, Zeitlin said, if Raymond’s allegations had any merit. To back this up, he showed me (but did not let me have) a few emails on his mobile device that appeared as if he were conversing with someone at the Treasury about a potential job working for Lew.

“At first, in a moment of just weakness and madness, I agreed to go forward with at least learning more about [the position] and talking to people,” Zeitlin said. “[Lew] vetted me fully. They offered me the role and at that point. … I went back to Tina, my wife, and she said, ‘Do you remember what happened the last time you went through this process?’ And so I backed out at that point. If anything about [Raymond] or others actually had validity to it, there’s not a chance they would’ve offered me actually a bigger role than [the U.N. position].”

But that doesn’t seem to check out either. Lew, who now works at Lindsay Goldberg, a private equity firm in New York, said through a colleague that he had no idea who Zeitlin is and that he never considered him for a job at the Treasury. Zeitlin, in response, referred me to Sarah Bloom Raskin, a former Lew deputy. She declined to comment about Zeitlin’s potential job at the Treasury.

Then Resnick, Tapestry’s communications chief — she was named as the company’s interim CFO on Tuesday — joined full throttle in Zeitlin’s defense. She emailed a wide-ranging assault on any of the questions that appeared to have sunk Zeitlin’s U.N. nomination in 2009. “Actually, there is, in fact, no more to this than a Jim DeMint political attack,” she wrote. (DeMint is a conservative former U.S. representative and senator from South Carolina. He did not respond to an email seeking comment.)

“DeMint and other far right-wing senators were desperate to take down another Obama nominee before the full Senate vote. … Jide was collateral damage in a wider game,” Resnick wrote. (At one point, she went so far as to claim that Zeitlin had learned of Raymond’s existence only when the White House “diligenced the claim.”)

By July, Clare Locke, a law firm representing Zeitlin, had dispatched a letter threatening a libel suit. The letter alleged that I had misled Zeitlin by originally telling him I intended to publish the article in Air Mail and that a subsequent potential publisher — the Foundation for Financial Journalism, for whom I am treasurer and a director — is a tool for short-sellers and vested financial interests. (Air Mail’s director of communications, Anna Bradlee, said, “A few months ago, the allegations that William Cohan presented to us could not be fully corroborated. He’s a dogged reporter so he took the piece elsewhere, and as of yesterday he was able to get corroboration from Tapestry itself.” The Foundation for Financial Journalism said it decided not to publish the article because, as its editor, Roddy Boyd, put it, “small shop, lots of stories, limited bandwidth.” I’m a freelance writer, and sometimes articles commissioned for one publication are later published elsewhere.)

Clare Locke subsequently sent a second letter accusing me of using a fictitious name and email address — I did not — and placing an electronic “tracking bug” on an email — their term for using a “read receipt” to confirm that Coach’s former CEO had received my email.

In the end, Zeitlin’s downfall occurred before a word was published. He had some common language in his employment contract in which he stipulated that he had never been the subject of any allegation of “harassment, discrimination, retaliation, or sexual or other misconduct” and agreed that “any act or omission” on his part that could have a “material adverse effect” on Tapestry and “its reputation” would be considered “cause” for his termination. Only days after Tapestry’s lawyers began asking questions, Zeitlin stepped down.