In the United States v. Woodward et al., Executors of Woodward case in 1920, the Supreme Court dealt with issues related to estate taxation. The central question was whether or not a federal estate tax could be levied on property that had been transferred by a decedent prior to their death but remained within their control and possession until they passed away. In this particular case, Mr. Woodward had transferred ownership of certain properties into trust for his children while retaining life interest in them; he continued to receive income from these properties until his death. The executors of Mr. Woodward's will argued against the inclusion of these trusts' value in calculating the gross amount subject to federal estate tax, asserting that since legal title had been transferred before death, it should not be included as part of his taxable estate. However, the Supreme Court disagreed and upheld lower court rulings which held that such transfers were indeed subject to federal estate taxes because despite transferring legal title during life time, Mr.Woodward retained beneficial use and control over those assets till his demise - thus making them part of his gross taxable state at time of death.

The dissenting opinion in the case of United States v. Woodward et al., Executors of Woodward, argued that the majority's decision to tax a deceased person's estate based on its value at death rather than its value when bequeathed was incorrect. The dissenters believed this interpretation contradicted previous court rulings and misinterpreted the intent of Congress when it passed relevant taxation laws. They contended that an estate should not be taxed for increases in property values occurring after a testator’s death because such gains are speculative and uncertain until realized by sale or other disposition. Furthermore, they asserted that taxing unrealized appreciation could lead to inequitable results as estates would bear different tax burdens depending on market fluctuations between date-of-death and date-of-sale which are beyond their control.