How Jeffrey Epstein Became Core Club’s ‘Guardian Angel’

6 February 2026

When Jennie Enterprise founded Core Club in 2005, a soon-to-be important person put up financing: Jeffrey Epstein.

With his initial investment, Epstein secured himself a lifetime membership to the exclusive members-only club. And more than a decade later, as Core Club grew to a hub for real estate’s elite, Epstein stayed involved in high-level business operations, introducing Enterprise to potential partners and offering advice on possible business structures. Enterprise also maintained a warm personal relationship with the disgraced financier and sex offender, who was accused of sexually abusing dozens of underage girls.

Epstein’s fellow founding members included Aby Rosen of RFR, Steven Roth of Vornado Realty Trust and Stephen Schwarzman of Blackstone Group. The club also made headlines for a high-profile lawsuit with developer Michael Shvo, as well as disagreements with Rosen and RFR.

The Real Deal previously reported that Epstein took credit for the club’s success, writing, “I helped put them in biz,” in 2018. A spokesperson for Core denied at the time that Epstein had any business development role at the club.

But the latest tranche of files released by the Department of Justice shows that when Core Club’s finances were ailing in 2015, Epstein stepped in as a confidante and connector.

“[Just] keeping you in the loop,” Enterprise wrote to Epstein in 2016, in the midst of business negotiations. Attached in the email appear to be sheets of corporate tax returns and income statements for the club.

“Updating my guardian angel ….love you !” she wrote that same year.

In response to the latest batch of emails, the spokesperson reiterated the claim that Epstein played no business development role in Core Club.

“We stand by our initial statement that this individual had nothing to do with the founding of the company, or ‘putting CORE: in business’,” the spokesperson said in a statement.

An early business partner

Epstein first became involved in Core Club at its inception in the early 2000s. He paid $100,000 as a founding member, alongside 150 other investors, according to a spokesperson for Core.

Emails between Epstein’s staff refer to his investment in an entity called Core Club 55th Street LLC, most likely referring to the club’s first location at RFR’s 66 East 55th Street.

In 2014, Enterprise began a campaign to ask founding members to cancel their promissory notes to help the club pursue debt restructuring, according to paperwork in Epstein’s files.

“Based upon the Club’s own financial analysis, the Club has determined that in order to reach viability, among other things, it needs at least 90% of our Founding Members to execute and return the Settlement Agreement and affirm the cancellation of their promissory notes,” Enterprise wrote to founding members.

Epstein appears to have gone through with the cancellation, paying a discounted annual rate of $7,600 for his Core Club membership.

The spokesperson for Core said that Epstein rarely used the Club’s member facilities and mostly received skin treatments, which are available to nonmembers.

There are scores of emails detailing Epstein’s facial appointments with Dangene Enterprise, Jennie’s wife.

Dangene and her staff sent Epstein a birthday email in 2019, months after a Miami Herald investigation raised widespread awareness of Epstein’s role as a serial abuser of children.

They wrote in large purple font, “WE LOVE YOU VERY MUCH.”

An almost-workout plan

By 2015, Epstein had introduced Core Club to a personal associate: inventor and investor Nathan Myhrvold.

Emails detail that Myhrvold visited Epstein’s island in 2011 and sent him books and pistachio ice cream in 2013. “Pussy doesn’t FedEx well,” he wrote the financier, who pled guilty to procuring a minor for prostitution five years earlier.

A spokesperson for Myhrvold said he knew the financier from TED conferences and as a donor to basic scientific research. “He regrets that he ever met him,” the spokesperson said.

Epstein first referred Myhrvold as a member of the club, according to a club spokesperson. Enterprise then pursued a business deal with him.

It was a difficult time for Core Club, which owed its landlord roughly $6.8 million in unpaid rent and was pursuing a debt restructuring plan, according to correspondence from Enterprise.

Emails detail that Enterprise kept Epstein up to date about her talks with Myhrvold, sometimes asking for advice or wanting to hop on the phone to get info and prepare for meetings. He appeared to provide ideas as to how they could structure the deal.

At one point, Enterprise sent him a draft term sheet for Myhrvold’s investment. Epstein OK’d the file, saying she should send it before the would-be investor got cold feet.

“Do not copy me just send to him,” Epstein wrote to Enterprise, “with a note that you are very excited to have him as a partner.”

At least once during the negotiations, Epstein met privately with Myhrvold.

Enterprise, who was being assisted by Rick Ross, chair of hotels and leisure at global law firm Dentons, was trying to get out of a business arrangement with Aby Rosen, whom Epstein separately claimed to have known for 20 years.

Enterprise, Myhrvold and their teams worked out a potential plan: they would start a new company together, with Myhrvold making a $6 million convertible loan. They would move Core Club’s intellectual property into the new company and license it back to the old LLC. The new company would buy existing debt from AES Holdings and then forgive it. Enterprise would be paid $100,000 for past services and then use that same money to pay off Rosen and RFR.

The parties explained via email that they had designed the deal to shield Myhrvold and the new company from taking on Core Club’s tax risk.

The goal specifically appears to be to allow Myhrvold’s investment to avoid taking on cancellation of indebtedness income but still use existing net operating losses to shield income from taxes, said Michael Meisler, a lecturer in taxation at Baruch College and former partner at Ernst & Young, who reviewed a selection of emails but was otherwise unfamiliar with the deal or the parties.

Cancellation of indebtedness income occurs when one’s debt is cancelled, and that canceled debt can then be taxed as income by the IRS.

Net operating losses can be carried forward in time to decrease taxable income. The deal was designed to protect that ability to shield the new income from Myhrvold’s investment.

“When you have a highly structured transaction that goes out of its way to say, ‘We are doing this just to achieve this desired tax result,’ that’s usually a red flag for something that probably has a lot of risk to it,” Meisler said.

Spokespersons for Core Club and for Myhrvold said no deal between the parties ever materialized.

“CORE: has consistently been presented with business opportunities throughout our twenty-year history,” the spokesperson said in a statement. “This individual [Epstein] referred a member who then presented a business opportunity a decade after the founding of the company.”

Neither Dentons, Ross nor representatives for Rosen responded to a request for comment.