On Jeffrey Epstein’s 62nd birthday in 2015, Kathy Ruemmler, a former Obama White House counsel, emailed to wish him well, writing, “I hope you enjoy the day with your one true love. :-)”
The billionaire sex offender replied with a raunchy note and an apparent reference to masturbation: “They say men usually gvie [sic] a name to their penis,” Epstein wrote in a typo-laden email, as it “would be inappropriate to make love to a total stranger.”
That newly released exchange, and others, add fresh details to the relationship between Epstein and Ruemmler, one of the highest-paid lawyers in the country. Ruemmler has said that she got to know Epstein through her work as a lawyer and that the two were “friendly in that professional context.”
Amid the hundreds of email exchanges reviewed by CNN that discuss Epstein’s legal battles and reputational problems, there are other more personal communications between the two, including plans for a proposed trip to Epstein’s island and gifts he’d given her.
In some of their back-and-forth messages, Ruemmler discussed personal matters in her life, expressed gratitude for their “friendship,” and concluded her messages with “xo” and “xoxo.”
After receiving Epstein’s racy reply to her birthday well-wishes, Ruemmler responded, “Hard to believe that there is still an open question about whether men are [the] inferior gender.”
Many of the messages in the newly released files contain typos and spelling errors. It’s unclear whether some of those occurred as the Department of Justice prepared the millions of pages of documents for public release last month.
Ruemmler, who is now the chief legal officer at Goldman Sachs, has weathered numerous news stories in recent weeks examining her relationship with the disgraced financier.
In a statement to CNN in December, she said, “I knew Jeffrey Epstein in a professional capacity when I served as head of the white collar defense group at Latham & Watkins, and he was a business referral source. I did not represent him and was not compensated by him. I was one of a number of lawyers Epstein informally reached out to for advice.”
Ruemmler has repeatedly said she regrets ever knowing Epstein and that she had “no knowledge of any new or ongoing unlawful activity on his part.”
Following the most recent release of Epstein files, Ruemmler and her communications team referred CNN’s questions about her birthday exchange with Epstein to her attorney, Tom Clare.
“The fact is: Ms. Ruemmler does not make any statement about Epstein’s penis,” Clare told CNN in an email. “She does not reference it. She does not joke about it. She does not banter with Epstein about it. She does not accede to Epstein’s unsolicited, gratuitous remarks about men and their penises. Nothing. Her participation in the entire exchange in [sic] limited to (1) wishing Epstein a happy birthday; (2) ridiculing Epstein for the remark; and (3) exiting the exchange.”
CNN has previously reported on the depth of Ruemmler’s relationship with Epstein, including how she was among a small group of advisers to help him ward off legal and reputational risk during the final years of his life.
But the latest batch of messages released on January 30 reveal in far greater detail the nature of that work, showing how Ruemmler advised Epstein on lawsuits brought by his accusers and coordinated responses to journalists, including regarding a proposed network TV interview with a victim that never aired.
In one exchange with Epstein in February 2015, Ruemmler addressed a Crime Victims’ Rights Act lawsuit brought by Epstein’s accusers, which sought to reopen his 2008 plea deal after he’d been indicted for sex crimes.
Ruemmler wrote to Epstein, “I told you that this CVRA case is about money.” And in another message after inquiring about which lawyer was handling the case, Ruemmler wrote, “Victim’s rights, my ass.”
In another message from July 2015, which has not been previously reported, Ruemmler forwarded Epstein a New York Times story which featured critics of sex offender registries, like the one Epstein had been listed on for several years by then.
“Did you see nyt story re: extreme reac=/misapplication of sex offender registry? Thinking about whether there is a= opportunity there,” Ruemmler wrote of the New York Times story published the day before.
Jennifer Connelly, a spokeswoman for Ruemmler, said Epstein, at times, “sought informal advice, and she provided feedback based on her understanding at the time, without any formal involvement.”
Months later, Ruemmler wrote to Epstein, “friendships goes two ways – getti=g you some peace with respect to all of this legal shit is important to me.”
In another email sent that year during a first-class trip to Europe that Epstein had booked for her, Ruemmler wrote that she was “grateful” for their relationship and signed off with “Xo.”
And in an email from September 2016, Epstein wrote to Ruemmler: “thansk for your friendhsip and help.”
She replied, “Back at you, and always.”
Connelly, Ruemmler’s spokesperson, declined to answer some of the detailed questions from CNN but said Ruemmler “has done nothing wrong and has nothing to hide. Nothing in the record suggests otherwise.”
Epstein was “a man of a thousand faces,” the spokesperson said. “Ms. Ruemmler only saw the one he put on to win people over and gain credibility and acceptance. Her views were shaped by that and his denials of any wrongdoing other than what he had pled guilty to years prior.”
Connelly said Ruemmler “has been clear and consistent from the outset: she knew him through her work as a criminal defense attorney, shared a client with him, received referrals from him, and was friendly in that professional context.”
Ruemmler, Connelly added, “has deep sympathy for those harmed by Epstein and if she knew then what she knows now, she never would have dealt with him at all.”
‘Day trip’ to the island
According to the newly released files, Ruemmler at one point inquired about taking a trip to Epstein’s private island.
In January 2017, Ruemmler asked Epstein whether she could take a “day trip” to the island while she was traveling in the Caribbean. Later that year, after Hurricane Irma severely damaged the island, Ruemmler mused about traveling to the island to help Epstein clean up. It is unclear whether either visit ultimately occurred.
A Goldman Sachs spokesperson previously said Ruemmler never visited the island.
Two years later, Ruemmler thanked Epstein for what appear to be gifts he sent her. “Am totally tricked out by Uncle Jeffrey today! Jeffrey boots, handbag, and w=tch!” she wrote in a January 2019 email. “Thank you to Uncle Jeffrey!!!” she wrote in another email after receiving a gift.
Goldman Sachs has so far stood by Ruemmler, telling CNN after the new batch of files were released, “It’s well known that Epstein’s MO was to do unsolicited favors for and provide unsolicited gifts to his many business contacts.”
Ruemmler left the Obama White House in 2014 and went to work for Latham & Watkins as head of its white-collar defense group. The firm previously told CNN that Epstein was never a client. In 2020, Ruemmler joined Goldman Sachs and was later promoted to become the firm’s chief legal officer.
The email exchanges between Ruemmler and Epstein have caught the attention of the House Oversight Committee, which has been conducting a broad examination of how the federal government and others handled Epstein’s cases and related files. Their latest efforts have included working to obtain testimony and documents from witnesses and institutions connected to him.
A source familiar with the committee told CNN they were interested in questioning Ruemmler.
“We want to hear from anyone who may have information on Epstein and his crimes and she’s not exempt from that,” the source told CNN.
A recently unsealed federal court filing in a civil suit against Epstein’s estate has also provided a window into the assistance Ruemmler gave to Epstein as he faced potential legal and media scrutiny.
Ruemmler is included in a batch of emails the estate sought to shield from disclosure by asserting attorney-client privilege over them. The court document, known as a privilege log, provided detailed descriptions of those emails but concealed their contents.
But in the recently released Epstein files, at least some of these emails are revealed in full.
Among the more notable instances they document is how Ruemmler, along with a small group of advisers, helped Epstein and his since-convicted accomplice Ghislaine Maxwell navigate a potentially damaging public relations situation.
In April 2015, ABC News was planning a Good Morning America segment on Virginia Roberts Giuffre, who would allege that for years she was sexually abused and groomed by Epstein and Maxwell and that they trafficked her to powerful men.
After ABC News reached out to Epstein for comment regarding Giuffre’s allegations, emails show Ruemmler coordinated strategy with Epstein.
Ruemmler wrote in one email that Giuffre’s “fantastical claims are – on their face – not credibl=.”
In one email chain dated April 22, 2015, Ruemmler asked if Maxwell would give a statement to ABC News. Epstein replied: “her lawyer provided a long winded letter t= counsel. she will do as you suggest howver.”
Ruemmler wrote that Maxwell “needs a short, on the record statement=that they will have to read on air.”
“Some suggested edits in the red-line attached,” Ruemmler wrote in an email on April 23, 2015, though the attachment was not provided in the emails released by the Justice Department.
According to the Epstein estate’s privilege log, that same day Ruemmler sent a document titled “Letter to ABC (Draft 3)kr.doc” to Epstein and his personal attorney Martin Weinberg.
The following day, April 24, 2015, Weinberg sent a formal letter to ABC News on Epstein’s behalf — a copy of which was released in November by House investigators.
In that letter, Weinberg argued that Giuffre’s allegations were uncorroborated, outdated, and contradicted by other evidence, and warned ABC News that airing the interview would be “grossly negligent or worse.”
The ABC News interview with Giuffre never aired.
A spokesperson for ABC News previously pointed CNN to a past statement on the incident: “At the time, not all of our reporting met our standards to air, but we have never stopped investigating the story.”
In April 2018, Epstein emailed an associate about an award-winning architect accused of sexual misconduct and wondered if the man had legal counsel. “Kathy ruemmmler has done 6 of these now for me,” Epstein wrote.
“This is false,” Connelly told CNN. “Ms. Ruemmler did NOT do ‘6 of these’ for Epstein. Ms. Ruemmler had no control over how Epstein characterized her or their interactions. She was not his defender. She never advocated on his behalf with any third party – not the press, not a court, not a government official.”
‘Fly you to the island’
In a January 16, 2017 email, Epstein asked if he could have a plane pick Ruemmler up in St. Lucia to fly her to “the island.”
“If you like , i can have a pl=ne pick you guys up in st lucia on sat , fly you to the island. =nbsp; and you can go home from there on sunday , if it is not too much trav=l.?!” Epstein wrote.
Ruemmler asked if she could take a “day trip” that coming Saturday.
“Off the grid all day with t=e tobacco farmers in NC. Our flight Sunday back to NY is from St Luci=. Can we take a day trip to the island on Sat or is it too far?” Ruemmler responded.
A week later, on Tuesday, January 24, 2017, Ruemmler and Epstein sent joking emails about former President Barack Obama visiting his island that coming Saturday when discussing a Daily Mail article on Obama, who had just left office, visiting the private island of billionaire Richard Branson.
“Should we invite him to meet you and lisa on my isla=d saturday. . ?” Epstein wrote, suggesting an additional person named “Lisa,” would be visiting the island.
“Much nicer than bransons. . more private=as well,” Epstein said in another email.
“If that came out, it would really be a scandal! Can you =magine what the Daily Mail would do?” replied Ruemmler.
Epstein then asked what time he should send his plane for Ruemmler: “What time sunday. My plane will be there.”
“10:30?” Ruemmler replied. Epstein appeared to coordinate a jet to pick up Ruemmler and “Lisa,” referencing a copy of Ruemmler’s passport.
“im planning on p=cking you up sun as early as you like,” he wrote in another email.
The planned visit appears to have fallen through.
“I fully understand lisa position. . not wrong,” Epstein wrote on January 28, 2017.
“Yeah – still too much risk in the air,” replied Ruemmler, who appeared two days later on Epstein’s New York schedule for lunch.
Ruemmler also relied on Epstein at times for career advice.
In October 2014, Ruemmler, who had left the Obama administration months before, sent Epstein a draft public statement declining further consideration for the position of US attorney general and asked for his feedback.
In 2018 and 2019, Ruemmler sought Epstein’s advice on whether she should pursue jobs with a top tech company, as first reported by the Financial Times. In July 2018, she emailed Epstein a draft letter she intended to send to Sheryl Sandberg, then a top executive at Facebook, after a meeting.
In 2019, she emailed with Epstein just after she met with top executives at Facebook, now Meta.
Epstein, in turn, was supportive of Ruemmler’s career and coached her through the yearlong process with Meta. He was also mindful that his association with her could hurt her chances.
In March 2019, Epstein wrote to Ruemmler that “i also prefer you to be clean from me when dealing with faceboo=.”