In the case of Woerishoffer et al., Executors v. United States, 1925, the U.S Supreme Court dealt with an issue related to estate tax law. The executors of Mrs. Woerishoffer's will contested a decision by the Commissioner of Internal Revenue who had included in her gross estate certain property transferred during her lifetime but over which she retained control until death. The executors argued that these transfers were not intended to take effect at or after death and thus should not be subject to taxation under Section 402(c) of the Revenue Act of 1918. However, both lower courts ruled against them on this point. The Supreme Court affirmed these decisions stating that although Mrs.Woerishoffer did transfer ownership rights during her lifetime, she maintained significant control over those assets until her death - including income benefits and power to revoke or alter beneficiaries' interests without their consent - hence they are taxable as part of her gross estate upon death according to existing laws.

In the dissenting opinion for Woerishoffer et al., Executors v. United States, Justice Oliver Wendell Holmes Jr. disagreed with the majority's interpretation of tax law and its application to gifts made in contemplation of death. He argued that a gift given within two years prior to death should not be presumed as being made in anticipation of impending demise unless there is clear evidence supporting this assumption. According to him, such presumption was arbitrary and unjustified by any natural or necessary inference from the facts stated in the statute itself or known generally about human behavior around mortality and gifting practices. Therefore, he believed that it was inappropriate for these gifts to be subject to estate taxes simply based on their timing relative to death without further proof demonstrating they were indeed motivated by an awareness of imminent end-of-life.