Leon Black’s $158 Million Relationship With Jeffrey Epstein Was Supposed to Be About Tax Advice, but Years Later, the Questions Have Only Grown
A September 13 report by the New York Post examined William D. Cohan’s book Money to Burn, which traces Leon Black’s rise at Apollo Global Management and the decisions that damaged his standing on Wall Street. Published on September 8, 2026, the book revisits Black’s personal and financial relationship with Jeffrey Epstein, the convicted sex offender who advised him on complex financial matters. The publisher’s description of the book identifies that relationship as one of the factors behind Black’s departure from Apollo in 2021.
The central question is not whether the two men knew each other, but what Epstein actually did for Black and why their arrangement generated payments totaling at least $158 million. Previous investigations, published documents and newer congressional inquiries have examined different aspects of their dealings without producing a universally accepted explanation of every transaction. The result is a story that stretches beyond one billionaire’s professional downfall and into broader questions about money, influence and accountability.
Black Built His Fortune Through High-Stakes Wall Street Deals
Black established his reputation in finance after working at Drexel Burnham Lambert, the investment bank associated with the expansion of the junk-bond market during the 1980s. After Drexel collapsed in 1990, he and other veterans of the firm helped build Apollo into a major private equity company by pursuing investments and acquisitions that other investors sometimes considered too risky. The business expanded substantially, creating enormous wealth for Black and fellow Apollo leaders Marc Rowan and Josh Harris.
Black’s success rested on a reputation for financial sophistication, aggressive negotiation and the willingness to pursue complicated deals. Apollo developed into a major investment firm, making its founder one of the most prominent figures in the industry. That background makes the arrangement with Epstein particularly striking because the payments later attracted questions about the value of the services Black said he had received.
Epstein Entered Black’s World During the 1990s
According to the account of Cohan’s book, Black was introduced to Epstein in 1996, well before the relationship became a major public controversy. Epstein had cultivated connections with wealthy and influential people, presenting himself as someone capable of resolving complicated financial and personal problems. His connection with Black eventually developed into a longstanding relationship involving both professional advice and personal access.
Epstein’s involvement reportedly extended beyond occasional consultations. The book’s account describes him as eventually serving on the board of Black’s family foundation, bringing him into another part of the billionaire’s private world. The relationship therefore involved more than a series of isolated business transactions between two people who barely knew each other.
Epstein Became an Adviser on More Than Tax Returns
Black maintained that Epstein provided valuable assistance with tax planning, estate arrangements, philanthropic matters and the operation of his family office. These responsibilities involved complicated financial structures that could affect how a wealthy investor managed assets, trusts and charitable commitments. Epstein also became a source of advice about matters extending into Black’s personal financial administration.
The explanation for the relationship has consistently centered on the services Epstein provided rather than on any acknowledged criminal purpose. Apollo’s later review described Epstein’s work as involving trust and estate planning, taxes, philanthropy and family-office operations. The breadth of those responsibilities helps explain why the relationship continued for years, although it does not independently establish whether every payment was appropriate or proportionate to the work performed.
Emails Revealed a Relationship With Unusually Large Financial Expectations
Cohan’s account includes emails in which Epstein portrayed himself as a trusted adviser who believed Black had not adequately compensated him for his work. Rather than limiting his requests to conventional professional fees, Epstein reportedly suggested alternatives such as real estate, artwork or financing for an aircraft. Those proposals illustrate how the arrangement could blur the boundaries between ordinary financial consulting and a much more personal relationship.
The correspondence also presents Epstein as someone who believed his access to Black and his contributions to the billionaire’s affairs deserved substantial financial recognition. Black, meanwhile, reportedly said that the arrangements were largely informal and that he did not have a clear understanding of the overall amount paid across the years. The disparity between Epstein’s demands and the eventual total helped turn the relationship into a subject of intense scrutiny.
The $158 Million Figure Became the Defining Detail
An outside investigation commissioned by Apollo and conducted by the law firm Dechert identified $158 million in payments to Epstein for services provided to Black and his family office. The figure became central to public reporting about the relationship because it represented an extraordinary sum for the kind of tax and estate planning advice Black said he had received. Apollo published its January 2021 announcement of the independent review, including details about the investigation’s methods and findings.
According to that announcement, Dechert examined more than 60,000 communications, including emails, text messages and documents, and interviewed more than 20 relevant individuals. The review covered Black’s professional relationship with Epstein at a time when the latter’s criminal history had already raised serious concerns. Although the investigation provided an account of the services and the payments, the size of the total continued to invite questions from lawmakers and journalists.
A Senate Investigation Put the Total Even Higher
In March 2025, Senator Ron Wyden’s office announced findings from a separate investigation into Black’s financial relationship with Epstein. The Senate Finance Committee’s review identified documents indicating that Black’s payments totaled $170 million, which was $12 million more than the amount identified by Apollo’s board investigation. Wyden’s office said the discrepancy had not been adequately explained.
The committee also reported finding evidence that money paid by Black had helped finance Epstein’s operations in the U.S. Virgin Islands. Its investigation referred information to federal agencies and sought further records concerning Epstein’s sources of financial support. These were findings and allegations advanced by the Senate investigation, not a judicial determination that every payment was unlawful or that Black participated in Epstein’s crimes.
Lawmakers Questioned the Fees and Financial Structures
The scrutiny intensified in March 2026, when Wyden released additional findings and renewed questions about the payments. According to the Senate Finance Committee’s account of its investigation, Epstein’s compensation for the financial services Black described was approximately 30 times the rates Black paid other advisers he already employed. The committee also identified a $10 million payment routed through a tax-exempt charitable organization and raised questions about the structure’s purpose.
Documents cited by the committee included an email from Epstein’s lawyer discussing how the charitable arrangement could reduce public disclosure and maximize tax deductions. Wyden argued that these records raised questions about the explanations Black had previously given for the payments. Black’s stated position remained that Epstein had provided financial advice, while the Senate investigation questioned whether that account adequately explained the amounts and arrangements involved.
Records Also Raised Questions About Payments to Women
The financial investigation expanded beyond the fees Epstein received directly from Black. A March 2026 Senate inquiry discussed documents concerning money paid to women and allegations that Epstein had helped arrange payments or surveil women connected to Black. Those findings raised additional questions about the nature of Epstein’s role in Black’s personal affairs, although the claims must be distinguished from proven criminal conduct by Black.
Separately, coverage of Cohan’s book by Vanity Fair discussed earlier New York Times reporting that Epstein had helped facilitate approximately $20 million in payments from Black to about a dozen women, at least some of whom had been sexually involved with him. That reporting raised questions about whether Epstein’s responsibilities went beyond conventional tax and estate planning. Black has denied wrongdoing, and the existence of payments or financial arrangements does not by itself establish that a crime occurred.
Apollo’s Independent Review Reached a Different Emphasis
When concerns about the relationship threatened to affect Apollo, the company commissioned an outside review through its independent board conflicts committee. Dechert concluded that the fees paid by Black or his family office were for bona fide tax, estate planning and related services, and that the advice had been reviewed by professional advisers. The investigation also reported finding no evidence that Black was involved in Epstein’s criminal activities.
Apollo further stated that the firm itself had never retained Epstein for services and that Epstein had never invested in an Apollo-managed fund. These distinctions were important because the review examined Black’s personal relationship with Epstein separately from Apollo’s business operations. However, the later questions raised by Wyden and congressional investigators show that the review did not end public scrutiny of the arrangement or resolve every issue concerning the total payments.
Black Left Apollo as Separate Allegations Emerged
The controversy became a major turning point in Black’s career during early 2021. After Apollo announced the findings of its independent review in January, former model Guzel Ganieva publicly accused Black in March of harassment, coercion and abuse, claims he denied. Those accusations were separate from the questions concerning Epstein’s fees, although they added to the pressure surrounding Black’s personal conduct.
Black resigned from Apollo on March 22, 2021, leaving the executive position at the firm he had helped build while remaining a major shareholder. His departure marked a dramatic change for a financier whose career had been defined by his influence over the company. The resignation did not itself resolve the questions about Epstein, and the financial relationship continued to attract scrutiny long after Black left the firm.
Cohan’s Book Revisits the Mystery Without Providing a Definitive Answer
Money to Burn examines Black’s professional rise, internal rivalries at Apollo and the personal controversies that contributed to his loss of power. But the book does not establish a definitive alternative explanation for the $158 million in payments, nor does it present proof that the money was paid to facilitate Epstein’s criminal activity. Instead, it revisits the explanation Black provided while placing that account against the unusual scale of the arrangement.
During a public discussion of the book, Cohan acknowledged the limits of what he could establish about the relationship. As Vanity Fair reported, he said Black maintained that the payments were for tax, business and estate advice, while Epstein’s death meant that the other participant in their conversations could no longer be questioned. The book therefore offers additional context about their relationship without resolving the central issue that has continued to trouble investigators.
Congressional Oversight Brought the Relationship Back Under Scrutiny
In 2026, the House Oversight Committee began examining Black’s relationship with Epstein as part of a broader investigation into the government’s handling of the Epstein and Ghislaine Maxwell cases. Black appeared for a voluntary transcribed interview on June 26, but questions about nondisclosure agreements became a point of conflict. Chairman James Comer subsequently issued subpoenas requiring Black to provide the agreements and appear for a deposition.
The committee’s announcement of the two subpoenas explained that Black had declined to answer questions about the terms and substance of the nondisclosure agreements during the interview. Investigators sought those records as part of their examination of how Epstein maintained relationships with influential people and whether confidentiality agreements might have concealed information relevant to the investigation. The dispute would soon become a separate legal battle over the committee’s authority.
Black Challenged the Subpoenas and Missed a Deposition
On September 3, 2026, Black sued the House Oversight Committee and Comer, arguing that the investigation had exceeded Congress’s constitutional authority. According to Reuters’ reporting on the lawsuit, Black described the inquiry as an unlawful fishing expedition and argued that the demands for nondisclosure agreements threatened the privacy of women who had no connection to Epstein’s crimes. His lawyer said the action was intended to challenge what the defense considered an abuse of congressional power.
Black also failed to appear for the deposition scheduled for September 3 after the committee had accommodated a request to delay his earlier appointment. He maintained that he had learned of Epstein’s criminal activity only after the financier faced federal sex-trafficking charges in 2019 and denied participating in abuse or sex trafficking. The disagreement left the committee without the testimony and documents it had demanded, while the underlying questions about the financial relationship remained unresolved.
The House Found Black in Contempt of Congress
The House Oversight Committee advanced a resolution recommending that Black be held in contempt after he failed to comply with the subpoenas. On September 16, the House approved a resolution to hold him in contempt of Congress by unanimous consent, following the committee’s earlier action. The decision represented a significant escalation in the dispute over his cooperation with the investigation.
In its official statement on the contempt finding, the committee said Black had failed to appear for the required deposition and had not produced the requested nondisclosure agreements. The contempt action concerned his refusal to comply with congressional demands, rather than a judicial finding that he had participated in Epstein’s crimes. It nevertheless added another consequential development to the record of Black’s relationship with Epstein and the efforts to investigate it.
A Separate Civil Lawsuit Was Dismissed in October
The scrutiny surrounding Black also included a separate civil lawsuit brought by a woman identified as Jane Doe, who alleged that Epstein had introduced her to Black before Black sexually assaulted her in 2002, when she was a teenager. Black strongly denied the allegations. On October 16, 2026, a federal judge dismissed the lawsuit after the plaintiff requested dismissal, stating that her medical condition made continuing the litigation unsafe.
As The Guardian reported, the plaintiff said her decision was not a retraction of her allegations or an acceptance of Black’s position, but reflected her inability to continue the case. Black’s lawyer said the dismissal was voluntary and involved no settlement, compromise or inducement. The outcome ended that particular legal proceeding, but it did not determine the disputed facts surrounding every allegation or resolve the separate questions about Black’s financial relationship with Epstein.
The Biggest Questions About the Relationship Remain Unanswered
The available record establishes that Black and Epstein maintained a longstanding personal and financial relationship, that Black paid Epstein extraordinary sums for services he described as financial advice, and that the relationship contributed to serious consequences for Black’s career. The independent review commissioned by Apollo found no evidence that Black was involved in Epstein’s criminal activities, while subsequent Senate and congressional inquiries raised further questions about payment totals, financial structures and the information held by people around Epstein. Those differing findings need to be understood in their respective contexts rather than treated as interchangeable conclusions.
Cohan’s book brings the relationship back into focus, but its publication does not settle the financial questions that have persisted for years. The later investigations have added information and sharpened disputes without establishing a single, complete explanation of the arrangement or a finding that Black participated in Epstein’s criminal conduct. For now, the most significant unresolved issue remains what the payments covered, what the documentary record can prove and whether further evidence will clarify the relationship between two men whose association became one of the most consequential controversies of Black’s career.
