It was probably the most surreal image to come out of the Jeffrey Epstein saga. Forget the private islands or the flight logs for a second. In 2019, news broke that a bizarre oil painting of Bill Clinton in a blue dress and red high heels was hanging prominently in Epstein’s Manhattan townhouse.
The image was jarring. Clinton is depicted lounging in a chair in the Oval Office, looking right at the viewer, pointing a finger as if he’s caught in the middle of a joke—or a scandal. For years, the internet spiraled into deep-state theories about why this existed. Was it a secret message? A trophy? Honestly, the truth is way more mundane, but the way it resurfaced in the "Epstein Files" release in late 2025 has kept the fire burning.
The Artist Behind "Parsing Bill"
Most people assume some shadowy figure commissioned this as a psychological power play. Nope. It was actually a student project.
The artist is Petrina Ryan-Kleid, an Australian-born painter who was attending the New York Academy of Art. She painted it back in 2012. It wasn't some grand conspiracy; it was part of her master’s thesis. The piece is titled "Parsing Bill." When the news first hit, Ryan-Kleid was basically blindsided. She told reporters she had no idea Epstein even owned the thing. She had sold it at a fundraiser called the Tribeca Ball for about $1,300. To her, it was just a "silly school artwork" meant to satirize how the media caricatures American presidents.
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Why the dress?
The blue dress is a pretty obvious nod to Monica Lewinsky. But there's a specific detail most people miss: the dress in the painting looks remarkably similar to one worn by Hillary Clinton at the 2009 Kennedy Center Honors. It’s a weird, layered satire of the entire Clinton era, mashed into a single frame.
Ryan-Kleid also painted a companion piece called "War Games." That one shows George W. Bush sitting on the floor of the Oval Office, playing with paper airplanes and two fallen Jenga towers. It’s equally provocative, but it didn't end up in a billionaire’s mansion, so it didn't get the same level of infamy.
How it Ended Up in Epstein’s House
The mystery isn't why it was painted, but why Jeffrey Epstein bought it.
Witnesses who visited his $56 million home on the Upper East Side said the painting was hard to miss. It reportedly hung in a room to the right of the entrance. One source told the New York Post that anyone who saw it would "laugh and smirk."
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Epstein was known for having "unsettling" art. His collection included:
- Prosthetic eyeballs.
- A custom-made human chessboard.
- A life-sized doll hanging from a chandelier.
In that context, a painting of a former president in drag fits the "edgelord" vibe Epstein seemed to cultivate. It was likely a conversation starter—a way to show off his proximity to power while simultaneously mocking it.
The Second "Blue Dress" Secret
Interestingly, "Parsing Bill" isn't the only time a blue dress has haunted a Clinton portrait.
The official presidential portrait of Bill Clinton, painted by Nelson Shanks and unveiled in 2006, has its own hidden secret. Years later, Shanks admitted that he purposely included a shadow on the left side of the painting. That shadow? It was cast by a blue dress on a mannequin that was in the room while he was painting.
Shanks told the Philadelphia Daily News in 2015 that he could never get the Lewinsky scandal out of his mind. He wanted the shadow to represent the "metaphorical stain" on Clinton's presidency. The Clintons reportedly hated that portrait and wanted it removed from the National Portrait Gallery.
So, you've got two different artists, years apart, using the same garment to make a point about Clinton's legacy. One was subtle and "official," the other was loud, weird, and ended up in the home of a convicted sex offender.
The 2025 "Epstein Files" Resurgence
You might think this story died in 2019, but it got a second life recently. In December 2025, the U.S. Department of Justice released a massive trove of previously redacted documents from the Epstein investigation.
Among the photos of the townhouse's interior was a high-resolution shot of Parsing Bill in its original location. The release reignited the debate about Clinton’s ties to Epstein. While Clinton has denied knowing anything about Epstein’s crimes, the visual of that painting in Epstein’s hallway remains a powerful, if uncomfortable, piece of imagery.
The files also confirmed that Epstein owned a signed photo of Clinton, further complicating the public perception of their relationship.
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Actionable Insights: How to Evaluate Viral Art
When you see a piece of art like the painting of Bill Clinton in a dress go viral, it’s easy to get lost in the "why." Here is how to look at it through a critical lens:
- Check the Origin: Most "creepy" political art starts as student work or satire. High-profile figures (or their decorators) often buy these pieces precisely because they are provocative.
- Separating Artist from Owner: Petrina Ryan-Kleid is a legitimate artist whose career was temporarily derailed by the fact that a monster bought her homework. Just because a piece of art is found in a bad place doesn't mean the artist shared the owner's values.
- Symbolism vs. Reality: In art, a dress is rarely just a dress. Whether it’s Ryan-Kleid’s literal blue dress or Nelson Shanks’ shadow, artists use these motifs to comment on history.
If you're looking for the original work, Ryan-Kleid still has prints listed on Saatchi Art, though she has mostly moved on from political satire to more abstract figurative work. The original canvas? Its current whereabouts are unknown, likely tied up in the ongoing liquidation of the Epstein estate.
To dig deeper into the actual connections between these figures, you should look into the flight logs released during the Ghislaine Maxwell trial rather than the art on the walls. The art tells us about Epstein’s ego; the logs tell us about the history.
Next Steps for Research
- Review the December 2025 DOJ document release to see the full context of Epstein's art collection.
- Compare the Nelson Shanks official portrait to "Parsing Bill" to see how different artists handle the same historical scandal.
- Look up Petrina Ryan-Kleid’s "War Games" to understand the full scope of her 2012 thesis.