JS’s first recorded interaction with the law occurred at the age of thirteen when he served as a witness in a case brought by his and older brother against , a prominent citizen of , New York. On 27 March 1818, and signed a promissory note to pay sixty-five dollars in grain for the purchase of two horses. During the subsequent summer, and his sons , JS, and worked on the farms of and his widowed mother, performing various services. also sold goods to the Smiths and rented them a plow. The Smiths paid fifty-three dollars toward the note on 18 August 1818. However, in January 1819, before the remaining sum could be paid, and brought a “” suit against , asserting that the horses had proven unsound. After an initial hearing before Abraham Spear, a justice of the peace in , New York, the plaintiffs requested a jury trial, which occurred on 6 February 1819. The witnesses included JS and , and the jury awarded the plaintiffs $40.78 in damages and $4.76 in court costs. The next day, hired an attorney to appeal the verdict to the court of common pleas as well as to initiate a new suit against the Smiths. The suit was heard at the August 1819 term. However, a scribal ambiguity in the court of common pleas docket renders the outcome of the case uncertain.

This calendar lists all known documents created by or for the court, whether extant or not. It does not include versions of documents created for other purposes, though those versions may be listed in footnotes. In certain cases, especially in cases concerning unpaid debts, the originating document (promissory note, invoice, etc.) is listed here. Note that documents in the calendar are grouped with their originating court. Where a version of a document was subsequently filed with another court, that version is listed under both courts.