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Crude Email Exchange with Jeffrey Epstein That Ended Kathy Ruemmler’s Stint as Goldman Sachs’ Top Lawyer
Crude Email Exchange with Jeffrey Epstein That Ended Kathy Ruemmler’s Stint as Goldman Sachs’ Top Lawyer

The resignation of Kathy Ruemmler, former chief legal officer of Goldman Sachs, followed the public release of email exchanges with Jeffrey Epstein that many described as unusually familiar — and in at least one instance, crude.

Read more: Who Is Kathryn Ruemmler? Former Obama White House Counsel Named in Epstein Files

What Was in the Emails?

According to reporting based on Justice Department document releases, the exchanges spanned roughly 2014 to 2019, well after Epstein’s 2008 conviction for soliciting a minor.

The emails were not limited to formal communication. Several details stand out:

1. The “xoxo” Sign-Off

In one birthday message, Ruemmler reportedly ended her note with “xoxo,” a sign-off commonly associated with personal affection rather than professional correspondence.

In isolation, that phrase might seem minor. But in the context of a high-profile financier already convicted of sex crimes, the tone raised questions about the nature of their relationship.

2. The Crude Sexual Remark

The most damaging detail involved Epstein’s response within the same email thread. He reportedly made a vulgar, sexually explicit joke referencing his genitals.

The exchange was not described as legal in nature. It was casual. The crude element did not appear as coded language or ambiguity. It was explicit enough to be widely characterized in media coverage as obscene.

There is no public indication that Ruemmler initiated sexual language. However, the fact that such a comment appeared in an ongoing friendly thread — rather than being rebuked or cutting off communication — intensified scrutiny.

The vulgarity itself became a focal point in headlines because it crossed from “poor judgment” into something more personal and inappropriate in tone.

How Personal Was the Relationship?

Beyond the crude exchange, other details suggest the relationship went beyond strictly professional interaction.

Reports indicate that Ruemmler:

  • Referred to Epstein in at least one message as “Uncle Jeffrey.”

  • Maintained communication for years after his conviction.

  • Accepted luxury gifts, including high-value items.

None of the released materials show evidence of criminal coordination. However, the sustained contact and warmth in tone made it difficult to characterize the relationship as purely transactional or legal.

The emails were not framed as legal advice memos. They included social greetings, travel references, and informal language.

Where the Vulgarity Became a Turning Point

The explicit remark about Epstein’s body appears to have been the tipping point in public reaction.

Why?

Because it shifted the narrative:

  • From “maintained contact”

  • To “engaged in friendly, crude banter”

For a corporate chief legal officer, tone matters. Once a sexually explicit joke becomes part of the documented record, the relationship no longer reads as distant or reluctant. It reads as socially comfortable.

That distinction shaped media coverage and internal pressure.

Level of Involvement: Professional, Social, or Something Else?

Based on available reporting, the emails suggest:

  • Sustained communication over multiple years

  • Personal warmth in tone

  • At least one sexually crude exchange

  • Gift acceptance

There is no public evidence of romantic involvement.

There is no allegation of participation in criminal conduct.

But the language used in the correspondence — especially the “xoxo” closing and the vulgar response — created the impression of familiarity rather than professional distance.

In reputational terms, that distinction was significant.

Why the Crude Email Mattered More Than the Timeline

Contact alone was controversial. But the explicit sexual remark made the relationship harder to defend as purely formal.

In crisis situations, a single vivid detail often outweighs years of context. Here, the obscene comment became that detail.

It was concrete. Quotable. Headline-ready.

And once it entered the public record, it reframed the entire email history.