In the case of Steele v. Drummond in 1927, the United States Supreme Court was tasked with determining whether a will that left an estate to a charity could be contested by relatives who were not named as beneficiaries. The testator's brother and sister-in-law challenged the validity of his will, which left most of his property to various charities and educational institutions. They argued that he had been unduly influenced by others when making his will due to mental incapacity caused by illness. However, after examining all evidence presented at trial including medical testimonies regarding the testator's mental state at time of drafting his last testament, it was concluded that there wasn't sufficient proof showing undue influence or lack thereof capacity on part of deceased while executing said document; hence upholding its legitimacy under law despite familial objections raised against it.

In the dissenting opinion for Steele v. Drummond, Justice Holmes disagreed with the majority's decision to reverse a lower court ruling that had denied recovery of damages for an alleged breach of contract. He argued that there was no clear evidence indicating any wrongdoing by the defendant in this case. The plaintiff claimed that he had been promised certain payments upon completion of his work, but failed to provide sufficient proof supporting these claims. Furthermore, Justice Holmes pointed out inconsistencies in the plaintiff’s testimony and highlighted lack of corroborating witnesses or documents as reasons why he believed it was unjustified to award him damages based on mere allegations without concrete proof. Therefore, according to Justice Holmes' dissenting view, upholding such a verdict would set a dangerous precedent where anyone could make unsubstantiated claims against another party and be awarded compensation without having to prove their case beyond reasonable doubt.