Epstein billed Leon Black $158M as a ‘work of art’

Jeffrey Epstein was paid $158 million by private-equity founder Leon Black between 2012 and 2017 for tax and estate work Epstein described as a “work of art.” Documents released by prosecutors and reviewed by investigators show the payments went to a set of complex transactions involving trusts, art and promissory notes.

The work centered on the Black 2006 Family Trust. Lawyers found the trust had overpaid Black by about $142 million, creating a risk that the trust could be treated as defective and that its assets would be pulled back into Black’s taxable estate. Epstein proposed replacing the trust’s Apollo equity, then worth about $1.6 billion, with a promissory note from Black. Part of that note was structured as an art-backed loan using pieces from Black’s collection as collateral.

The substitution was intended to remove distributable equity Black could not accept without creating tax consequences, while preserving the trust’s tax benefits. Epstein’s work also included use of grantor-retained annuity trusts, splitting assets into multiple holdings to seek valuation discounts, and transactions that generated losses in an art-related business that could offset gains elsewhere.

An outside law firm retained by Apollo, Dechert LLP, reviewed the files and concluded Epstein’s strategies saved Black between $1 billion and $2 billion in taxes and that the $158 million in fees were for legitimate advice. The firm described the first project Epstein worked on for Black as validating and noted the substitution plan resolved a major estate problem for the family trust.

Senator Ron Wyden and other officials have raised questions about the scale and purpose of the payments. Bank of America filed suspicious-activity reports with U.S. authorities tied to roughly $170 million in Epstein-related transactions connected to Black. Wyden has said the size of the fees is hard to reconcile with routine tax advice and has called for further review by tax and law enforcement agencies.

Documents include email exchanges in which Epstein wrote in May 2016, “Leon, you hired me to produce a work of art. it was not inexpensive. the value far exceeds any other piece in your collection — by FAR.” Internal messages and financial records show disputes over repayment of funds tied to art purchases and planning work.

One contested episode involved a 2016 effort to complete a tax-deferred like-kind exchange for artworks. Epstein wired $30 million to Black to meet a sale deadline; record-keepers later treated the transfer as a loan. Epstein repaid $10 million but did not return the full balance. Correspondence shows Epstein warning that disclosing some tax arrangements could expose earlier transactions. Tension over unpaid fees and loans contributed to the collapse of their financial relationship in 2018.

The documents also show transactions tied to Phaidon, a publishing business Black bought and Epstein later controlled. A sale that produced tax losses was structured at a reduced valuation; outside lawyers flagged audit risk when related parties were proposed as buyers. A revised deal closed and was documented internally as reducing federal and state taxes by several million dollars.

Black has told the House Oversight Committee that Epstein “solved a massive estate problem for me, that none of the experts and lawyers I consulted had been able to solve.” Black has denied knowledge of Epstein’s criminal conduct. Dechert’s report cleared Black of wrongdoing on Epstein-related matters.

The Justice Department’s release of Epstein-related files provided emails, financial records and legal papers that investigators are examining. Congressional committees, the IRS and financial institutions continue to review the transactions and determine whether any laws were violated.