In Connelly v. United States, the Supreme Court resolved a long-standing dispute over how to treat redemption obligations when valuing a decedent’s shares in a closely held company. The Court held that redemption obligations do not offset corporate-owned life insurance proceeds obtained to fund a redemption, upsetting a long-standing practice. While the Court undoubtedly reached the right conclusion, it (1) failed to address important arguments the parties and amici raised; (2) assumed away the effects of discounts, premiums and different valuation techniques, which would have complicated the analysis without changing the conclusion; and (3) muddied the water somewhat by leaving open the possibility of a different outcome where companies use operating assets to fund a redemption. This Article lays out the various authorities that bear on this question, sets forth additional grounds supporting the Court’s conclusion, including the arguments the Court sidestepped, addresses the complexities avoided by using a simple hypothetical and explains why the reasoning applies equally to situations where operating assets are used to fund a redemption. Finally, the Article identifies different ways taxpayers can use insurance to fund redemptions while avoiding the results in Connelly.