The U.S. Supreme Court case Irving Trust Co. et al., Executors, et al. v. Day, Executor (1941) revolved around the interpretation of a will and testament in relation to federal estate tax laws. The decedent's will included provisions for charitable donations that would be deducted from the gross estate before calculating taxes owed under federal law at that time; however, these deductions were contingent upon whether certain individuals survived him by more than five years or not - if they did not survive beyond this period, their share was to go towards charity instead. The issue arose when one beneficiary died within the five-year period but after the executor had already filed an estate tax return without accounting for potential reversionary interests as part of deductible transfers to charities due to uncertainty over beneficiaries' survival status at filing time. In its decision, the Supreme Court ruled against Irving Trust Company and other executors who argued for a refund based on later events affecting charitable deductions initially unaccounted for in filed returns because such contingencies were unknown then. The court held that deductibility of charitable contributions should be determined based on facts known at death rather than subsequent occurrences altering those circumstances posthumously – thus denying any claim for refunds sought by executors due to changes happening after initial filings.

In the dissenting opinion for Irving Trust Co. et al., Executors, et al. v. Day, Executor, Justice Roberts expressed concern over the majority's interpretation of New York law and its application to federal estate tax laws. He argued that the majority had misinterpreted both state and federal statutes in a way that allowed them to avoid paying taxes on certain portions of an estate left by a deceased individual who was not domiciled in New York at their time of death but held property there through a trust fund established during their lifetime. According to Justice Roberts, this interpretation contradicted previous court decisions and created unnecessary confusion about how these types of cases should be handled in future instances.