Freshly unsealed emails from the late convicted sex offender Jeffrey Epstein’s private accounts have dramatically ratcheted up scrutiny on the Democratic political establishment, particularly the orbit of former President Barack Obama. The documents, part of a broader document release stemming from civil litigation against Epstein’s estate, center on an alarming exchange involving Kathryn Ruemmler, who served as Obama’s chief legal advisor, the White House Counsel, from 2011 to 2014.
The ‘Boss’ Reference and the 2014 UNGA
The most explosive revelation focuses on correspondence from 2014, during the week of the United Nations General Assembly (UNGA) in New York. At this time, Barack Obama was the sitting U.S. President and scheduled to address the UNGA.
Epstein repeatedly urged Ruemmler—then in private practice at Latham & Watkins—to coordinate a meeting with “your boss.” Given Ruemmler’s most recent and prominent role as the President’s top lawyer, and the context of the UNGA event, conservative commentators have seized on the phrase as an apparent direct reference to Obama.
One unsettling exchange captures Epstein attempting to lure Ruemmler to his events:
Epstein: “It doesn’t look like you’re prioritizing your schedule very efficiently… This is UNGA week. The boss will be in town too… You are welcome guest at any of these dinners.”
Epstein then followed this with a chilling addendum:
Epstein: “Girls, careful. I will renew an old habit this week.”
He proceeded to list a series of high-profile guests, including former Treasury Secretary Larry Summers and current CIA Director William Burns. The disclosure amplifies long-standing questions about why so many senior Obama-era officials maintained contact with Epstein years after his 2008 conviction for procuring a minor for prostitution.
Data Points: High-Level Meetings and Disparaging Comments
The emails and calendar entries provide concrete data points illustrating Epstein’s deep entanglement with global elite:
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Dozens of Meetings: Kathryn Ruemmler is confirmed to have met with Jeffrey Epstein dozens of times after leaving her White House Counsel role.
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Bill Clinton Slur: In a separate exchange, Ruemmler joked darkly about “fat-shaming” New Jersey Turnpike travelers, and later offered a scathing assessment of former President Bill Clinton after a personal falling-out, describing him as a “true sociopath with no conscience.”
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CIA Director’s Visits: Epstein’s calendar confirms that William Burns—currently the CIA Director under President Biden—met with the financier multiple times at his infamous Manhattan townhouse in 2014. At the time of these meetings, Burns was serving as the Deputy Secretary of State in the Obama administration.
This Manhattan townhouse is the same location where prosecutors say Epstein trafficked and abused underage victims and allegedly filmed powerful men for potential blackmail.
While the Obama camp has previously stated that Ruemmler’s interactions with Epstein were professional and occurred after she left government service, the specificity of the “The Boss” reference, combined with the presence of other high-level officials like William Burns during the same time period (2014), has moved the once-fringe questions about Epstein’s political influence squarely into the national spotlight. Neither Ruemmler nor representatives for former President Obama have issued new public statements addressing the “boss” references.