In the 1945 case Commissioner of Internal Revenue v. Estate of Holmes, the U.S Supreme Court ruled on a dispute regarding estate tax valuation. The decedent had purchased bonds at a premium but they were worth less than their face value when he died. The executor valued them at market price for federal estate tax purposes while the Commissioner of Internal Revenue insisted they should be valued at par (face value). The court held that Treasury Regulations required that such bonds be included in gross estate "at their value as of the date" and not necessarily at par or maturity value unless it is clear from all circumstances that such was intended to represent actual cash or fair market values as of date used for valuing gross estates. Therefore, these bonds should have been included in his taxable estate based on their fair market value rather than face amount.

In the dissenting opinion for Commissioner of Internal Revenue v. Estate of Holmes, it was argued that the majority's interpretation of Section 302(c) of the Revenue Act was incorrect. The dissenters believed that this section should not be read as a limitation on what constitutes "property" for tax purposes but rather as an explanation or clarification about how to treat certain types of property transfers under specific circumstances. They contended that Congress intended to include all forms and types of property within its taxation power unless explicitly excluded by law, including future interests in trusts like those at issue in this case. Therefore, they disagreed with the majority's decision to exclude these trust interests from estate taxes based solely on their contingent nature and lack thereof immediate possession or enjoyment by beneficiaries.