In Winchester v. Heiskell, the United States Supreme Court was asked to decide whether a contract between two parties was valid. The contract in question was between the plaintiff, Winchester, and the defendant, Heiskell. Winchester had agreed to sell Heiskell a tract of land in Tennessee for $2,000. Heiskell had paid Winchester $1,000 as a down payment and agreed to pay the remaining $1,000 in two installments. Heiskell had failed to make the second payment, and Winchester sued to recover the remaining $1,000. The Supreme Court held that the contract was valid and enforceable. The Court noted that the contract was in writing and that the parties had agreed to all of its terms. The Court also noted that the contract was supported by consideration, as Heiskell had paid Winchester $1,000 as a down payment. The Court concluded that the contract was valid and enforceable, and that Winchester was entitled to recover the remaining $1,000 from Heiskell.

In Winchester v. Heiskell, the Supreme Court was asked to determine whether a contract between two parties was enforceable under Tennessee law. The majority opinion held that the contract in question did not meet all of the requirements for an enforceable agreement and thus could not be enforced by either party. Justice Field dissented from this decision, arguing that while certain elements of the contract may have been missing or incomplete, there were still sufficient facts present to support its enforcement according to Tennessee law. He argued that it should be up to a jury in Tennessee—not the Supreme Court—to decide if these facts are enough for an enforceable agreement and what damages should be awarded as a result of any breach thereof. In conclusion, Justice Field believed that since there were sufficient facts present which would allow for enforcement under state law, then it should ultimately fall upon a jury in Tennessee to make such determinations rather than having them decided by federal courts on appeal