Caesar was first enslaved by Jonathan Wells, Jr. (1684-1735) of Deerfield, Massachusetts. The year that Jonathan died, his wife, Mary Hoyt Wells moved next door into the home of her father-in-law, Justice Jonathan Wells, Sr. (1659-1739). She brought with her an enslaved woman and a "Negro boy" called Caesar. Jonathan Jr.'s probate inventory listed a "Negro Boy" valued at £100. This was probably Caesar. Mary had him baptized in 1741, and in 1745, he was "admitted to the Communion" of the church.
As early as 1742, Caesar had an account at Elijah Williams' store, where he purchased caps and buckles, among other things. On at least one occasion he paid for his purchases with two fox pelts.
In 1744, the Wells' daughter Mary (1727-1779) wed Timothy Childs, Jr. (1720-1781) of Deerfield and as early as 1746, Caesar is referred to in Williams' account book as "Cesar Timo Childs."
According to George Sheldon, author of the History of Deerfield, "'Cesar servant of Timothy Childs' is recorded several times as a soldier in the French and Indian Wars." (Vol. II, pg. 894)
Mary, Jr. and Timothy eventually moved to Turners Falls, Massachusetts, taking Caesar with them. He died there and Sheldon says of his passing, "friends from Deerfield visiting the Childses at the Falls found a negro slave whom they had taken with them from Deerfield sick unto death, and lying in a cold shed, on a rickety bedstead, with scanty covering, and not even a bed of straw under him, with nothing between his body and the bed-cords but an empty bed-tick. So passed away the Christian soldier." (History of Deerfield, Vol. II, pg. 894)