Caesar spent the early part of his life in servitude, enslaved in Woodstock by Samuel McClellan, a brigadier general in the Revolutionary War. Vital records show Caesar, a “Negro servant of Genl Samuel McLellan” was born on December 4, 1784 and that he was enslaved alongside children named Simon, Cit, and Prince. The records do not say whether the children were related or who their parents were. In 1799, McLellan placed an advertisement in the Windham Herald announcing the sale of a “stout, strong, healthy, negro fellow, eighteen years of age, a slave for life.” The young man  is said to understand “all sorts of farming business, and is able to do almost as much as any man in the state.” McClellan’s ad says the individual he is seeking to sell “was born in my house and never known to have a fit of sickness.” It is unlikely that Caesar was the young man featured in the advertisement, given the year and the man’s age, but the sale advertisement might have served as a cautionary tale for him. In 1803, McClellan took out another newspaper advertisement, this one offering “Ten Dollars Reward!” for the return of “a Negro Boy named Cesar, 18 years old, nearly six feet high, stout and well made, walks pretty erect, speaks fluently.” McClellan describes Caesar’s clothing and offers the following explanation for his departure, writing that Caesar has “lately been guilty of theft and made his escape through fear of punishment.” There is no record that Caesar ever returned.