Billionaire Harlan Crow’s gifts to Supreme Court Justice Clarence Thomas—including luxury trips aboard Crow’s 162-foot yacht—have prompted a congressional battle over whether Crow must disclose the details of these gifts.

A key question for investigators is whether Crow properly reported his generosity to the IRS, since substantial gifts can trigger federal gift-tax obligations. To claim related deductions, taxpayers must be operating a genuine, profit-seeking business.

As Pillsbury partner Michael Kosnitzky explains, “you have to be regularly chartering the yacht to their parties at fair market value”—typically through and independent charter broker—for a yacht owner to meet the legal standard of running a for-profit business.

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