It has long been held that if a contract is unconscionable in its terms, equity will not enforce it. But what exactly unconscionability encompasses is not easily described. In one of earliest and most famous descriptions of unconscionability, Lord Hardwicke explained, unconscionable bargain is one such as no man in his senses and not under delusion would make on one hand, and as no honest and fair man would accept on other. One contract scholar described unconscionability as whatever court can't stomach. Although these two descriptions provide some guidance, they are far from conclusive and serve only to provide a general theme of doctrine. In modern era, much scholarly ink has been spilt attempting to uncover and clarify doctrine of unconscionability. This paper proposes that unconscionability is a doctrine about fairness, and ultimate success or failure of a case involving doctrine generally hinges on status of parties and their relationship with one another. After reviewing a number of pre-UCC cases, I have categorized early unconscionability cases into three groups. They include, the old, the ignorant, and the shameful. These characterizations accurately represent three groups of cases that courts have generally been willing to declare unconscionable if there is a hint of unfairness or undue influence. The Old represents cases in which an unfair advantage or undue influence has been exerted against a widow or an elderly person, thereby resulting in an unconscionable agreement. The Ignorant generally refers to cases in which a trusting person, or as described by court, an ignorant person, has been taken advantage of by another who was in a confidential relationship with ignorant individual. Typically, this group involves agreements between lawyers and their clients. And finally, the Shameful group represents cases in which parties have reached an agreement, but court is simply unwilling to enforce contract because result would be extremely harsh or oppressive. Notions of fairness and undue influence underlie early American unconscionability cases. Although undue influence is a separate contractual defense, courts, while exploring and developing doctrine of unconscionability, relied on it in determining whether a particular contract was enforceable. As was also evident from cases I explored, each court framed unconscionability in different terms. Instead of an explicit, objective definition, courts analyzed parties and circumstances of each case to determine if unconscionability existed. This approach established foundation for a flexible doctrine aimed at preserving justice and preventing harsh and oppressive outcomes.