Yesterday I wrote a piece about “the Epstein files” and some links to sport and how “document dumps” can be both a journalistic blessing and a curse.
There are numerous other links to sport that I hadn’t spotted and this short piece today is postscript No1 to the original piece. Other postscripts may follow as various sources furnish me with more information about figures close to both FIFA and Epstein at various points in the recent past.
Today’s update relates to the majority owner of AS Monaco of France’s Ligue 1, a Russian oligarch called Dmitry Rybolovlev (below, pictured in 2012).
He has had close links to US President Donald Trump for years, and his name occurs 21 times in the Epstein files at the DOJ website.
As I wrote yesterday, it will take days, or perhaps even weeks or months for investigative teams to trawl through the three million new documents, 180,000 hitherto unseen images and 2,000 new videos relating to convicted sex offender Jeffrey Epstein, who died in August 2019, aged 66.
But as one Sporting Intelligence subscriber suggested to me, it’s possible that AI tools can speed up that process.
Taking that on board, I have used AI to further interrogate the DOJ Epstein database about Rybolovlev, a man who owns a major European football club, currently languishing in mid-table in France but also still in this season’s Champions League.
And this is what the AI concludes:
The relationship between Russian billionaire Dmitry Rybolovlev and Jeffrey Epstein, as revealed in the U.S. Department of Justice (DOJ) documents released in 2025 (often referred to as the “Epstein files”), appears to be indirect rather than direct or personal.
The files do not indicate any evidence of meetings, communications, or collaborations between the two men. Instead, Epstein references Rybolovlev in a handful of 2019 emails as part of broader conspiracy-laden speculations about financial dealings involving Donald Trump, Saudi Crown Prince Mohammed bin Salman (MBS), and potential money laundering or payoffs.
These emails were sent shortly before Epstein’s arrest on sex-trafficking charges in July 2019 and his subsequent death in August 2019. Below, I’ll outline the key revelations from the documents, focusing on Epstein’s mentions of Rybolovlev, the context, and the implications he drew.
Background context from The Epstein files highlight Epstein’s long-standing social and business ties to Trump, which dated back to the late 1980s and included shared social circles in Palm Beach, Florida.
A key flashpoint in their relationship was a 2004 bidding war over a luxurious oceanfront mansion called Maison de l’Amitié in Palm Beach. Epstein and Trump competed aggressively for the property, which was being sold out of bankruptcy. Trump ultimately won with a $41.35 million bid, reportedly outmaneuvering Epstein, who had initially led with $37.25 million. This incident is cited in the files as a possible catalyst for a falling out between the two men, with Epstein later insinuating in emails that Trump may have retaliated against him by tipping off authorities about his sex crimes (local police began investigating Epstein shortly after the sale).
Four years later, in 2008, Trump sold the mansion to Rybolovlev for $95m —more than double his purchase price—despite Rybolovlev never living in it and eventually demolishing it. This transaction has long fueled speculation about money laundering, as Rybolovlev was a fertilizer magnate with ties to Russian oligarch networks, and the sale occurred amid Trump’s financial difficulties post-2008 recession. The DOJ files do not provide new evidence of illegality in the deal but amplify Epstein’s 2019 theories about it.
Notably, this sale was briefly examined during Robert Mueller’s 2017-2019 investigation into Trump-Russia ties but yielded no charges.
Epstein’s emails portray Rybolovlev not as a personal acquaintance but as a figure in a web of international intrigue. Epstein speculated that Rybolovlev’s actions were part of hidden financial schemes benefiting Trump, possibly involving self-dealing or payoffs. He described Rybolovlev as someone who “knows all,” implying insider knowledge of Trump’s alleged secrets or corrupt dealings.
However, the files offer no substantiation for these claims, and the DOJ’s 2025 memo explicitly states there is no credible evidence of Epstein blackmailing prominent individuals or maintaining a “client list” for such purposes.
Specific Emails Mentioning Rybolovlev
The most direct revelations come from Epstein’s 2019 correspondence with author Michael Wolff (who interviewed Epstein extensively for his books on Trump). These emails, part of the DOJ-released tranche, show Epstein using Rybolovlev as a puzzle piece in theories about Trump’s finances and foreign influence. Epstein’s writing style is often rambling, typo-filled, and cryptic, reflecting his attempts to leak narratives to Wolff while reframing himself as a victim of Trump’s machinations.
Key excerpts:
January 15, 2019 (to Wolff, cc’d to Kathryn Ruemmler, a former White House counsel): Epstein outlines a theory that Rybolovlev may have been “buying the house from himself” through Trump as a front man. He parallels this to Trump’s business model of licensing his name for real estate deals owned by others, suggesting it was a way to launder or hide funds. Epstein references a 1997 art auction (the Ganz Collection, sold for $206 million) as an analogous example where hidden owners benefited. He implies this setup allowed Trump to earn fees while disguising true ownership, and ties it to the 2004 mansion bidding war, claiming Trump “set him up” afterward.
news.artnet.com
February 1, 2019 (to Wolff): A follow-up where Epstein provides “behind-the-scenes” details on the 2004 auction rivalry with Trump over Maison de l’Amitié. He sends it with a casual “have fun” note, continuing to insinuate that the fallout led to his legal troubles. Rybolovlev is mentioned indirectly as the eventual buyer, reinforcing Epstein’s suspicion of the 2008 sale as suspicious.
news.artnet.com
May 30, 2019 (exchange with Wolff): This is the most explicit mention, linking Rybolovlev to both the mansion and a high-profile art deal. Epstein writes: “is it a coincidence that the russian that bought the house in palm beach and knows all, is the same guy that sold a painting last year to mbs for 450 million dollars. that was only worth 1.5m?” The painting is Leonardo da Vinci’s Salvator Mundi, which Rybolovlev sold at Christie’s in 2017 for a record $450 million to an anonymous buyer later revealed as MBS (or a proxy). Epstein claims his “art guy” said the painting “wasn’t very good” and was vastly overvalued. When Wolff asks if MBS was “paying him [Rybolovlev] off? Why? Ideas?”, Epstein replies: “reminder trump overuled congress on yemen. maybe as a favor to trump. in exchange for yemen and iran support. . smells doesnt it?” He suggests the art sale was a covert payoff tied to Trump’s foreign policy favors for Saudi Arabia (e.g., overriding congressional blocks on arms sales amid the Yemen conflict). Wolff responds enthusiastically: “Starting to smell sweet, the way you put it!” Epstein adds details on the painting’s provenance, noting Rybolovlev bought it in 2013 for $127 million via dealer Yves Bouvier, who had acquired it for $80 million.
These emails are framed in the files as Epstein’s attempts to influence public narratives about Trump, possibly to deflect from his own scandals. Wolff later described Epstein as obsessed with such theories, using him as a source for books like Siege: Trump Under Fire (2019), where similar ideas about the mansion sale appear.
Broader Implications and Recent Developments
The DOJ files emphasize that Epstein’s speculations about Rybolovlev lack evidence and align with his pattern of promoting conspiracy theories to journalists.
No documents suggest Epstein and Rybolovlev ever interacted directly—Epstein seems to have known of him only through public reports and his Trump connections. However, the files tie into larger themes of transnational oligarch networks, with Epstein positioning Rybolovlev as a “go-between” in Russia-U.S. dealings.
In a 2025 update noted in analyses of the files, Rybolovlev appeared as part of Russia’s delegation in Ukraine peace talks in Riyadh, Saudi Arabia, sitting across from Trump’s team. This has renewed interest in Epstein’s 2019 claims, as it echoes his theories about Rybolovlev’s ties to MBS and potential influence operations. One document excerpt in the files speculates that Trump’s “long business relations with Russia” remain active, reinforced by Rybolovlev’s role in such talks, and frames U.S.-Russia negotiations over Ukraine as a “division of spoils” benefiting oligarchs like him.
Again, this is interpretive rather than evidentiary.