In the 1915 case of Willink, Executrix v. United States, the Supreme Court was asked to determine whether a legacy left by a deceased person to his wife could be taxed under an act passed in 1898 that imposed taxes on legacies and distributive shares of personal property. The decedent had made provisions for his wife in both real estate and personal property through his will. However, after paying off debts and expenses from the estate's assets, there were insufficient funds remaining to fulfill these provisions entirely. As such, part of her share came from selling some real estate properties which she argued should not be subject to tax as it fell outside the scope of "legacies" or "distributive shares". The court disagreed with this argument stating that regardless if her share came partially from sale proceeds of real estates; it still constituted as 'personal property' within meaning intended by Congress when they enacted said law hence is taxable.

In the dissenting opinion for Willink, Executrix v. United States (1915), Justice Holmes disagreed with the majority's interpretation of tax law and its application to this case. He argued that a life insurance policy should not be considered part of an estate if it was purchased by someone other than the deceased, even if they were named as a beneficiary in their will. According to Holmes, such policies are more akin to gifts or legacies rather than property owned by the deceased at their time of death. Therefore, he believed that these assets should not be subject to federal estate taxes under existing laws at that time.