“The Court’s little-noticed decision in Connelly v. United States, issued in June, throws a wrench into a common succession strategy for many closely held firms with more than one owner. In this strategy, a company buys life insurance on its owners so that when one dies, there’s cash to repurchase his or her stock. The goal is for the insurance payment to be tax-free and for the company to avoid the burden of funding a share repurchase from operating profits. In Connelly, however, the court ruled that the strategy didn’t provide the expected benefits. As a result, the owner’s estate owed nearly $900,000 more in estate tax….”The bottom line: For many closely held business owners, dealing with the Connelly decision requires help from advisers aware of both income- and estate-tax consequences. This advice won’t come cheap and could suck energy away from running the business. That’s an aggravation—but it’s not as big a pain as a surprise estate-tax bill.”
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