The U.S. Supreme Court case Commissioner of Internal Revenue v. Estate of Sternberger, Chase National Bank of New York, Executor (1954) revolved around the issue of estate tax deductions for charitable contributions made by a decedent's will. The decedent had left his residuary estate to charity but also provided that if any laws prevented this from reducing his gross estate for federal tax purposes, then the bequest would lapse and go instead to non-charitable beneficiaries. The IRS argued that because state law could potentially invalidate the charitable bequest under certain circumstances, it was not "presently ascertainable" at the time of death and therefore did not qualify as a deductible contribution under federal tax law. However, in its decision favoring Sternberger's Estate and against the Commissioner of Internal Revenue Service (IRS), 347 U.S. 46 (1954), Justice Reed wrote for a unanimous court stating that there was no real possibility that such an event would occur given existing legal precedent; thus making it possible to determine with reasonable certainty what portion of the residue would pass to charity at death itself - thereby qualifying it as 'ascertainable' enough for deduction.

In the dissenting opinion for Commissioner of Internal Revenue v. Estate of Sternberger, Justice Robert H. Jackson disagreed with the majority's interpretation of tax law and its application to this case. He argued that the estate should not be allowed to deduct certain expenses from its gross income because they were not "administration expenses" as defined by federal tax law but rather capital investments made by the decedent during his lifetime. According to Justice Jackson, allowing such deductions would create a loophole in tax laws that could potentially lead to significant revenue losses for the government. Furthermore, he contended that it was inappropriate for courts to make decisions about taxation based on their own notions of fairness or equity; instead, they should strictly adhere to statutory definitions and legislative intent when interpreting tax laws.