Urgency, pressure, persistence: Jeffrey Epstein's playbook for landing a billionaire client

The two great underwriters of Jeffrey Epstein's $630 million fortune were the billionaires Les Wexner and Leon Black, who entrusted him with managing their finances and ensuring their tax bills stayed as low as possible.

The Justice Department's files show that in the years before his 2019 arrest on sex-trafficking charges and jailhouse death, Epstein tried to nab another billionaire client: the real estate and media mogul Mortimer Zuckerman.

Zuckerman, who is now 88, at one point had a higher public profile than both Black, the former CEO and chairman of Apollo Global Management, and Wexner, the onetime owner of Victoria's Secret.

Between the 1980s and 2000s, Zuckerman was a frequent presence on cable news, occasionally floated himself as a national political candidate, and saw his romantic flings chronicled in tabloid newspapers.

Zuckerman — who is now worth about $2.7 billion, according to Forbes — is the former CEO of the real estate company Boston Properties and previously owned media outlets including The Atlantic, the New York Daily News, and Fast Company. He stepped away from some of those companies and public life about a decade ago "due to issues with his health," a person close to Zuckerman's family told Business Insider. He still owns US News & World Report, best known for its rankings of universities and hospitals.

Zuckerman's relationship with Epstein stretched back to at least the early 2000s. In 2003, they teamed up with producer Harvey Weinstein and writer Michael Wolff in a failed bid to buy New York magazine. In 2004, Zuckerman and Epstein financed the ill-fated relaunch of Radar, a celebrity gossip publication. The Epstein files show that Zuckerman contributed to Epstein's now-famous 50th birthday book and that, on at least one occasion, Epstein offered to set Zuckerman up with a woman. There's no indication in the files that Zuckerman had knowledge of Epstein's sex trafficking operation.

In 2013, Epstein pitched himself to Zuckerman as a financial manager, the Justice Department's records show.

The deal was never consummated, but the files show that Epstein, a college dropout, held himself out as one of the few people qualified to help Zuckerman with what he said were sophisticated financial problems that required "surgical" care.

He tried to convince Zuckerman to trust him above other people in his life — and to act quickly.

In the process, Epstein obtained deeply personal information about the billionaire's health, finances, and family — which he used to try to convince the people around the billionaire to put him in charge.

After repeated rejections over the course of two years, Epstein turned impatient.

"I hav not asked for the money that mort promised for getting my help and never following through," Epstein wrote in an email to Zuckerman's nephews, who also served as his investment advisors. "I would also appreciate you putting a brake on the daily news calling me a pedophile. I have been patient and my fondness for mort remains."

A draft contract, dated December 17, 2013, shows that Epstein proposed Zuckerman retain Southern Trust Inc., one of Epstein's companies in the US Virgin Islands, for "analyzing, evaluating, planning and structuring large discrete issues relating to Mr. Zuckerman's financial estate."

Zuckerman would pay $21 million for the first 10 months of Epstein's services. Paul Weiss, the Big Law firm that had also done estate planning work for Black, would represent Zuckerman's interests in the deal, according to another document. Terje Rød-Larsen, a Norwegian diplomat and friend of Epstein's, would get $1 million under the proposal.

Rød-Larsen's role in the potential arrangement is unclear from the documents. John Christian Elden, an attorney for Rød-Larsen, told Business Insider that Zuckerman and the diplomat were friends, and that his role in Zuckerman's estate planning was Epstein's idea.

"Mr. Zuckerman did not pursue Mr. Epstein's advice or proposals, and accordingly, these arrangements were never implemented," Elden said.

The Epstein files show that he began getting involved with Zuckerman's estate planning earlier in 2013. That April — following a dinner with Zuckerman at Epstein's Manhattan mansion that, according his calendar, also featured Ehud Barak, Jes Staley, Woody Allen, and Tom Pritzker — Epstein told Zuckerman he'd review his financial situation.

In the subsequent weeks, Zuckerman sent Epstein hundreds of pages of his personal financial information, including detailed valuations of his assets, documentation of his spending habits, structures of his trusts, his charitable contributions, and details about his separation agreement with his ex-wife.

Zuckerman's finances were in a dismal state, Epstein told him in a June 2013 email.

The trusts needed a "total re-do," Epstein said. The job required someone with knowledge of investing, tax, estate law, real estate partnerships, securities filings, and divorce law.

"it is a serious job that requires surgical intervention," Epstein added.

Epstein initially said it would take him 15 months to personally fix Zuckerman's finances and cost between $30 million and $40 million.

In an email two days later, Epstein made an emotional appeal to Zuckerman to listen to his advice, leaning on memories of their long relationship over the years.

"Mort , I have sat with you in dunkin donuts outside of sloan kettering bad time ,-- sat next to you at harry evans when you announced your engagement to Marla, hopeful times," Epstein wrote.

The following month, after phone calls and meetings, Epstein urged Zuckerman to move fast.

He said he had everything "ready to go" as soon as Zuckerman agreed to hire him. If Zuckerman delayed, Epstein warned, "hundreds of millions of dollars" would be at risk.

"Everything virtually from top to bottom will get redone. every trust , all investments , and build a financial structure," Epstein said with his typical idiosyncratic punctuation. "There is a huge amount of time required to fix and time getting shorter to fix it , if you want to file by the end of year."

In August 2013, Epstein told his personal lawyer and accountant that Zuckerman agreed to a $30 million fee and asked them to draft a contract.

But in emails to Epstein, Zuckerman was noncommittal, and Epstein shifted his approach. In a September 2013 email, he disparaged the team Zuckerman had surrounded himself with — including Zuckerman's nephews and investment advisors, Eric and Jamie Gertler.

"Mort , I recommend you hire professionals , not your nephews." Epstein wrote.

He said Zuckerman needed an "architect" for his financial life, and that leaving his nephews in charge would cause family strife. In Epstein's view, putting Zuckerman's nephew in charge of his daughter's upbringing would "wreak havoc" on his family."

When Zuckerman failed to sign the $21 million contract by the end of 2013 despite Esptein's warnings of dire tax consequences, the convicted sex offender tried to salvage the deal.

In a January 2014 email, Epstein told Zuckerman that he had already sunk resources into the project, stressed the supposedly dire straits of Zuckerman's finances, and told Zuckerman he would be getting Epstein at a bargain rate.

"I only have good feelings towards you, and am torn watching you do yourself financial harm," Epstein wrote.

Zuckerman told Epstein the financial structure he suggested just "doesn't fit."

"Jeffrey. I have now consulted with three tax specialists and they do not see the issues as you do," Zuckerman responded.

Epstein didn't give up. Following a June 2014 breakfast, Epstein wrote Zuckerman a long email "in order to memorialize our conversation." He said Zuckerman had told him he believed his estate-planning capability "was only decreasing" and that he wanted to delegate responsibility to a team.

"You agree that a committee should be set up to manage your financial. affairs," Epstein wrote. "your statement that you realize you are no longer capable of doing so . You suggested that Terje larson be in charge as you fully trust his judgement."

In the email, Epstein yet again pitched that he be put in charge, and suggested he could be paid with Boston Properties stock or part of Zuckerman's investment portfolio.

Zuckerman said he was "definitely going to proceed" with putting together a committee, led by Rød-Larsen, to run his financial affairs. There's no indication he ever did. When Epstein followed up the next month, Zuckerman told him, "i have my own pace."

Around this time, Epstein started emailing the people close to Zuckerman to convince them that he should be hired. In one email to the Gertlers, he suggested Zuckerman only backed out of an agreement for Epstein to be his financial manager because of "his illness."

"I feel awkward having to remind you of the role I played, expenses I incurred, agreements that were reached ( ask Terje larsen)," Epstein wrote. "I was the one that uncovered hundreds of millions in errors in his financial reporting. work done at his request."

Eric Gertler kept a firm but polite distance.

"I am not aware of the uncovering of the financial errors but do know that any of the suggestions of your advisors had been previously considered or previously implemented by Mort's lawyers and financial advisors," Gertler wrote. "Regardless, I am not interested in nor is it appropriate to go back and forth."

In October 2015, Epstein emailed Eric Gertler to suggest that he and Jamie Gertler take over Zuckerman's financial life entirely, citing the billionaire's health.

At around the same time, Epstein emailed Rød-Larsen with a different plan to help run Zuckerman's finances with the help of the nephews.

He suggested setting up "Mort" like a company. Rød-Larsen and "Harry" — a possible reference to Harry Beller, one of Epstein's in-house accountants — would be co-chairmen. Epstein would handle finances. Eric Gertler would run the day-to-day and health issues. And Jamie Gertler and Joel Klein, another friend, would oversee issues related to his children. Neither Beller nor Klein responded to Business Insider's requests for comment.

Epstein also reached out directly to Zuckerman, recommending that a team of people take over, but Zuckerman continued to decline his help.

"Am well on the way to completing the planning I need including the designation of appropriate representatives," Zuckerman told him. "Have discussed it with various friends And. Lawyers."

At that point, Epstein's tone turned harsh. In an email to the nephews two weeks after Zuckerman's rejection, Epstein suggested Zuckerman was taking drugs.

"i assume you are aware that hes now wacko on somethings," Epstein wrote.

By late 2016, their relationship seemed to have deteriorated.

Epstein told Zuckerman: "how you could let your paper call me a pedophile.???!!!I expect a public apology and a full retraction. . I have been a close friend of yours for years."

The files don't include a response from Zuckerman.