The U.S. Supreme Court case Rand et al., Executors of Rand, v. United States (1918) revolved around the interpretation of tax law and its application to estate inheritance. The executors of the will for a deceased individual named John F. A. Rand contested an additional assessment by the Commissioner of Internal Revenue on their inheritance tax return, arguing that certain deductions should have been allowed under existing laws at that time - specifically those related to debts owed by Mr.Rand's estate and funeral expenses incurred after his death in 1909. However, upon review, it was determined that these deductions were not permissible as they did not fall within the specific categories outlined in Section 38 of Act Aug 5th, 1909 c6-36 Statute at Large page112(Comp.Statute1913). This section only permitted deductions for claims against estates which are "wholly based on personal considerations" or "founded on a promise or agreement". As such,the court ruled in favor of United States government upholding additional assessments made by Commissioner.

In the dissenting opinion for Rand et al., Executors of Rand, v. United States, Justice Holmes 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 "in contemplation of death" should not be interpreted as one given with an awareness or expectation that death is imminent but rather as one motivated by "the thought of death," regardless if it was expected soon or far off into the future. This broader interpretation would include more types of transfers within taxable estates and thus increase government revenue from estate taxes. Holmes also emphasized that this understanding aligns better with legislative intent behind such laws which aim to prevent people from avoiding estate taxes through gifting before their demise.