Charles Wilkes, plaintiff in error, brought a case against Samuel Dinsmore. The dispute was over the ownership of certain slaves that had been purchased by Wilkes from Dinsmore. Wilkes claimed that he had paid for the slaves and should be given title to them; however, Dinsmore argued that he still owned them as payment for debts owed to him by Wilkes. The Supreme Court ultimately ruled in favor of Dinsmore on the basis that there was no evidence presented which showed any transfer of title or possession from himself to Wilkes. This decision established an important precedent regarding debt collection and property rights under common law: if one party claims they have already paid off their debt with another party but cannot provide proof of such payment then they are not entitled to receive anything in return until full payment is made according to contract terms agreed upon between both parties.

In the case of Charles Wilkes v. Samuel Dinsmore, the Supreme Court was asked to decide whether a contract between two parties could be enforced if it had been made in violation of an existing law. The majority opinion held that such contracts were not enforceable and should be declared void by courts of equity. However, Justice McLean dissented from this ruling on the grounds that enforcing contracts which violate laws would lead to chaos and confusion in society as people would have no incentive to obey laws if they knew their agreements could still be enforced despite breaking them. He argued that while some may suffer hardship due to this decision, it is necessary for upholding public order and morality since allowing illegal contracts would encourage citizens to break laws with impunity.