The Capital Trust Company, Administrator of Arnold v. Calhoun case in 1918 involved a dispute over the interpretation of a will and its associated property rights. The testator, Mr. Arnold, had left his estate to his wife for her lifetime use with the provision that upon her death it would pass to their children or their descendants per stirpes (proportionately divided between beneficiaries). However, one of the daughters died before Mrs. Arnold without leaving any issue or direct heirs behind which led to confusion about how her share should be distributed after Mrs. Arnold's death. The Supreme Court ruled that according to Connecticut law where this case was originated from, when an individual dies intestate (without a valid will), their property is passed on per stirpes among surviving siblings and descendants rather than being absorbed into the residual estate as argued by other parties involved in this litigation process. This decision clarified legal principles regarding inheritance laws especially those related with distribution rules under circumstances involving predeceased beneficiaries who die without direct heirs themselves.

In the dissenting opinion for Capital Trust Company v. Calhoun, Justice Holmes argued that the majority's decision was not consistent with established legal principles and precedent. He contended that a person should be able to dispose of their property as they see fit upon death, without interference from creditors or other parties who may have claims against them. In this case, he believed that Arnold had every right to leave his estate to his wife and children rather than using it to pay off debts owed by his business partner Calhoun. Furthermore, Holmes disagreed with the majority's interpretation of Connecticut law regarding joint liability in partnerships; he maintained that each partner is only liable for their own share of any partnership debt unless otherwise agreed upon in writing by all partners involved.