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A Senate committee is investigating whether $158 million that the billionaire investor Leon Black paid the disgraced financier Jeffrey Epstein for tax and estate planning services should have been classified as a gift, as part of a broader inquiry into tax-avoidance schemes by ultrawealthy individuals, according to a letter reviewed by The New York Times.

In addition to the fees that Mr. Black said he had paid Mr. Epstein, the Senate Finance Committee is looking into several trusts that Mr. Black used to save on taxes and advice that Mr. Epstein gave on art purchases, according to the letter, which the committee’s chairman, Senator Ron Wyden, sent to the private equity mogul on Monday.

Mr. Wyden, Democrat of Oregon, wrote that the committee was dissatisfied with the information that Mr. Black, a co-founder of Apollo Global Management, had provided it to date and requested his cooperation.

“A significant number of open questions remain regarding the tax-avoidance scheme you implemented with Epstein’s assistance, including whether the exorbitant amounts paid to Epstein should have been classified as a gift for federal tax purposes,” the senator wrote. Gifts exceeding an annual threshold in value are subject to federal taxes ranging from 18 to 40 percent.

A spokesman for Mr. Black, 71, said he had “cooperated extensively with the committee.” Whit Clay, the spokesman, added: “The transactions referenced in the committee’s letter were lawful in all respects; were conceived of, vetted and implemented by reputable law firms and tax and other advisers; and Mr. Black has fully paid all taxes owed to the government.”

In 2020, a law firm found that Mr. Epstein’s work had saved Mr. Black and his four children $2 billion in estate and gift taxes. The firm, Dechert, which Apollo’s board had retained to review Mr. Black’s dealings with Mr. Epstein, found that he had not done anything wrong. Mr. Black stepped down as chairman and chief executive of the private equity behemoth in 2021.

The investigation by the Senate Finance Committee is part of an inquiry into tax shelters that the superrich use to “avoid or evade paying federal taxes, including gift and estate taxes,” according to the 16-page letter. In April, the committee requested information from Harlan Crow, a billionaire real estate developer, about his tax treatment of gifts to Justice Clarence Thomas of the Supreme Court.

Mr. Wyden sent the letter just days after The Times reported that Mr. Black, who is worth an estimated $9 billion, had staved off a possible lawsuit by the U.S. Virgin Islands with a $62.5 million settlement.

The settlement, reached in January but not disclosed at the time, arose from potential claims that the Virgin Islands had developed against Mr. Black during its three-year investigation into Mr. Epstein’s sex-trafficking operation run partly from his private island residence off St. Thomas.

“Jeffrey Epstein used the money Black paid him to partially fund his operations in the Virgin Islands,” according to the settlement.

Mr. Black was a longtime social and business acquaintance of Mr. Epstein, who killed himself in 2019 after his arrest on federal sex-trafficking charges. Lawyers for his victims have estimated that Mr. Epstein, a college dropout with little training in tax and estate work, sexually abused 200 young women, many of them teenagers.

The Senate committee began investigating Mr. Black in June 2022 with a letter to Apollo, and then sought information from two major law firms that had worked for Mr. Black. The lawyers told the committee that he was unwilling to answer questions about the payments to Mr. Epstein.

Mr. Black’s lawyers did provide some information about several grantor retained annuity trusts, or GRATs, that were set up in 2006 to enable him to pass on shares in Apollo to his children in a tax-advantaged manner — while letting him continue to earn income from the investment. But Mr. Wyden said Mr. Black had not provided enough information for the committee to determine if the work performed by Mr. Epstein was a legitimate tax strategy.

Beginning in 2014, Mr. Epstein supposedly helped restructure the trusts to avoid a $1 billion gift and estate tax hit to Mr. Black and his family, according to the Dechert report.

A GRAT is a sophisticated investment vehicle that permits a person to keep collecting income from assets of all kinds — including stocks, real estate and art — and then hand them off to family members without paying the large gift or estate taxes normally associated with such transfers.

Mr. Epstein had often boasted that he was an expert in such trusts and collected hefty fees for helping a small number of wealthy people save money in taxes.

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