In the 1941 case Wilmington Trust Co., Executor, v. Helvering, Commissioner of Internal Revenue, the U.S. Supreme Court ruled on a matter concerning estate tax law and trusts. The issue at hand was whether or not an annuity purchased by a decedent for his wife could be included in his gross estate for taxation purposes upon his death. The court held that since the decedent retained control over the principal sum used to purchase the annuity during his lifetime and had power to revoke or alter it, it should indeed be included in his gross estate under Section 811(c) of the Internal Revenue Code (IRC). This decision clarified how certain types of property controlled by a deceased person are treated with respect to federal estate taxes.

In the dissenting opinion for Wilmington Trust Co. v. Helvering, Justice Frankfurter disagreed with the majority's interpretation of a clause in a will that allowed an executor to sell property "at such time or times as my said Executors may deem advisable." He argued that this language did not give the executors unlimited discretion to determine when and if they would sell the property, but rather was intended to allow them flexibility in managing estate assets during probate proceedings. The majority's interpretation, he contended, effectively rewrote the terms of the will by giving executors powers they were never meant to have under state law and common practice at that time. This misinterpretation led them incorrectly conclude that certain estate taxes could be deferred until after sale of properties which is against federal tax laws requiring immediate payment upon death regardless of whether properties are sold or not.