Caesar was one of seven children of Arthur and Joan Prutt, who were enslaved by Rev. Isaac Chauncey (1670-1745) of Hadley, Massachusetts. He was inherited by Isaac's son Josiah. At that time, Caesar was worth £20. (1759 Amherst, Massachusetts tax list)
In 1758, while still enslaved, Caesar fought for 45 days in Canada in the French and Indian War (1754-1763). He was a private in Elisha Pomeroy's Co., Col. Israel Williams Regt. (History of the Town of Amherst, Massachusetts, Carpenter, Edward W. & Charles F. Morehouse, 1896, p. 63)
In 1770, Caesar was caught poaching a deer, for which he paid a fine of £6. On another occasion he stole a sheep, but returned it and then left town. (Slavery in the Connecticut Valley of Massachusetts, Romer, Robert H., 2009, p. 187 & n109)
Caesar also served in the Revolutionary War (1775-1783), fighting as a patriot, although his enslaver was a Tory (supporter of England). His service is listed below:
Beginning in 1803, Caesar was autioned off at vendues in nearby Amherst, Massachusetts. In New England towns, before the establishment of poor farms or workhouses, those who could not support themselves might be auctioned off to the lowest bidder. This was called a “vendue”. At the town meeting on December 5, 1803, it was:
Voted, that Cesar Prutt, a negro and Town's Pauper, be set-up, at vendue, to the lowest bidder, to be kept, the year insuing with suitable vituals and clothing, and to be returned at the end of the year, as well clothed as he now is. He was accordingly set-up, as aforesaid, and struck-off to Aaron Merrick, he being the lowest bidder, at the Sum of forty one Dollars & fifty Cents, on the conditions above expressed. (History of the Town of Amherst, Massachusetts, p. 192)
He was auctioned off twice in 1805, first going to Daniel Moody for $48.25, and then going to Joel Kellogg at the end of the year for $51. In 1807, the year that he died, Caesar was auctioned off a final time for $65. He was 80 years old. (History of Hadley, Judd, Sylvester & Lucius Manlius Boltwood, p. 414)