In the case of Wolfsohn v. Hankin et al., 1963, the United States Supreme Court was asked to consider whether a New York law that allowed for an estate tax deduction for property transferred within three years of death violated the Due Process Clause of the Fourteenth Amendment. The plaintiff, Wolfsohn, argued that this provision unfairly discriminated against those who died shortly after making a transfer compared to those who lived longer. The court disagreed with her argument and upheld the constitutionality of New York's estate tax law. They found no violation in due process as it did not arbitrarily or capriciously affect any particular group or individual but applied uniformly to all decedents' estates irrespective of when transfers were made during their lifetime.

In the dissenting opinion for Wolfssohn v. Hankin, Justice Harlan argued that the majority's decision to reverse and remand was based on a misinterpretation of New York law. He contended that under New York law, an executor or executrix is not personally liable for any loss resulting from their failure to invest estate funds unless they acted in bad faith or with gross negligence. In this case, he believed there was no evidence suggesting such behavior by Mrs. Wolgast (formerly Mrs.Wolfsohn). Furthermore, he pointed out that even if she had invested the money as suggested by plaintiffs-appellees and lost it due to market fluctuations, she would still be held responsible for those losses according to the majority’s interpretation of state law which contradicts its own principles regarding fiduciary duties of executors/executrices towards estates they manage.