The U.S. Supreme Court case Wickwire v. Reinecke in 1927 revolved around the issue of estate taxation, specifically whether or not certain property could be included in a deceased person's gross estate for tax purposes. The petitioner, Mrs. Wickwire, was the executrix of her late husband's will and argued that his life insurance policy should not be taxed as part of his gross estate because he had no incidents of ownership at the time of death; it was owned by a trust which paid premiums and received benefits upon Mr. Wickwire’s death while he retained only an income interest during his lifetime with no power to alter or amend beneficiaries under the policy. However, the court ruled against Mrs.Wickwire stating that even though Mr.Wickwire did not have direct control over who would receive proceeds from his life insurance policies after death (incidents of ownership), they were still considered part of his taxable gross estate since he transferred them within two years before death without adequate consideration.

In the dissenting opinion for Wickwire v. Reinecke, Justice Oliver Wendell Holmes Jr. argued that the majority's interpretation of tax law was incorrect and overly narrow. He contended that a literal reading of the statute would lead to absurd results, such as allowing taxpayers to avoid paying taxes on income simply by transferring it into trust funds or other forms of property ownership. Instead, he believed that Congress intended for all forms of wealth transfer to be taxed equally under estate tax laws regardless of their form or timing. Therefore, he disagreed with the majority's decision to exempt certain types of transfers from taxation based solely on technicalities in how they were structured.