Douglass v. Douglass, Administrator was a United States Supreme Court case that dealt with the issue of a will's validity. The case involved the estate of a man named William Douglass, who had died without a will. His widow, Mary Douglass, was appointed as the administrator of his estate. She then filed a petition in the Supreme Court of the District of Columbia to have a will admitted to probate. The will was contested by the deceased's brother, John Douglass, who argued that the will was not valid because it had not been properly executed. The Supreme Court of the District of Columbia ruled in favor of Mary Douglass, finding that the will was valid. John Douglass then appealed the decision to the Supreme Court of the United States. The Supreme Court affirmed the lower court's ruling, finding that the will was valid and that Mary Douglass was the rightful administrator of the estate. The Court held that the will was properly executed and that the deceased had the capacity to make a valid will. The Court also held that the will was not invalidated by the fact that it was not witnessed by two people, as required by the law at the time.

In Douglass v. Douglass, the Supreme Court was asked to decide whether a will that left property to two of its testator's sons should be enforced as written or if it should be modified by the court in order to provide for an equal division between them. The majority opinion held that courts could not modify wills and must enforce them as written, even when doing so would lead to unequal distributions among heirs. However, Justice Field dissented from this decision on the grounds that such a ruling would allow injustice and inequality in inheritance decisions. He argued that since all persons are entitled under law to receive their just share of an estate regardless of any provisions made in a will, courts have both the right and responsibility to ensure justice is done by modifying wills where necessary. In his view, allowing unequal distributions based solely on what was stated in a will violated basic principles of fairness and equality before the law which he believed were essential for maintaining public confidence in our legal system.