In the case of Dickerman v. Northern Trust Company, 1899, the U.S. Supreme Court was tasked with determining whether a trust company could be held liable for losses incurred due to its negligence in managing property entrusted to it by an individual. The plaintiff, Mr. Dickerman, had given his property in Chicago to the defendant (Northern Trust Company) for management and later sued them when he suffered financial loss as a result of their alleged mismanagement and failure to pay taxes on time which led to penalties and interest charges. The court ruled that while trust companies are indeed responsible for exercising ordinary care and prudence in handling properties under their charge, they cannot be held accountable if losses occur despite this level of care being exercised - unless there is evidence proving gross negligence or fraud on part of the trustee. In this particular case however, no such proof was provided by Mr.Dickerman against Northern Trust Company; hence ruling favored towards defendant i.e., Northern Trust Company.

In the dissenting opinion for Dickerman v. Northern Trust Company, Justice Harlan argued that the majority's decision was inconsistent with established principles of equity and justice. He contended that Mr. Dickerman had a clear right to his deceased wife's estate because he had been her husband at the time of her death, despite their estrangement and pending divorce proceedings. According to Justice Harlan, it was unjust for Mrs. Dickerman’s trustees to withhold her property from him on grounds that they believed she intended to change her will before she died but did not have an opportunity due to sudden illness and subsequent death. The justice emphasized that intentions alone cannot override legal rights or obligations unless expressed in legally binding forms such as a revised will or testamentary document; mere assumptions about someone’s intent should not be used as basis for judicial decisions regarding property rights after their demise.