The Smithsonian Institution v. St. John, Executor of Wallace C. Andrews, Deceased case in 1908 revolved around the interpretation of a will and its bequest to the Smithsonian Institution. The deceased, Mr. Andrews had left his estate to the institution under certain conditions that were not met due to unforeseen circumstances (the death of a named individual). As such, there was ambiguity about whether or not the Smithsonian should receive any part of Andrew's estate at all. The Supreme Court ruled in favor of the Smithsonian Institution stating that despite these unmet conditions, it was clear from Andrew’s will that he intended for his wealth to benefit scientific research through this organization rather than defaulting back into his family line as per normal inheritance laws if no other beneficiaries are stated. This ruling set an important precedent regarding charitable donations and legacies by affirming that courts can interpret ambiguous terms within a person's will based on their apparent intentions rather than strictly adhering to legalistic interpretations.

In the dissenting opinion of the case Smithsonian Institution v. St. John, Justice Harlan disagreed with the majority's interpretation of Andrew J. Davis' will and its application to his estate tax liability. He argued that Davis intended for his entire estate to be used for charitable purposes, including a significant donation to the Smithsonian Institution, which should have exempted it from taxation under existing laws at that time. According to him, this was clear in Davis’ will where he expressed his desire “to promote education among my fellow men” by leaving most of his wealth to institutions like the Smithsonian and other educational entities across Montana and Washington D.C., thus qualifying as a charitable use under law.