Cicero was born around 1754. We first meet him in a December 1766 receipt for a pair of mittens “delivered your boy” to Edward Emerson in Boston. He was about twelve. Edward Emerson regularly sailed to the West Indies, and Cicero was likely bought there. If so, he was taken from his family and had to survive a new climate, a new city, and a Boston winter alone.

The Emersons later moved to Portsmouth, New Hampshire. When Edward died in Grenada in 1769, his estate inventory listed Cicero as “A negro boy named Cicero,” valued at forty pounds. He appears between a land lease and a hogshead of cider. His widow, Mary, then shipped him to Boston, writing that she wanted to keep him at her father’s house “as you have one already.”

In April 1770, Mary married Jonathan Bowman, and Cicero most likely traveled up the Kennebec River to the Bowman House that spring. He had come from Boston and Portsmouth, where many enslaved and free people of color lived. Pownalborough had only nine people of color in 1764. Cicero worked in the house and was also hired out to others, including a local ship captain, but Bowman collected the pay. A 1775 receipt records a doctor “bleeding Cicero.”

In the fall of 1775, as talk of liberty spread, Cicero ran. On November 6, Bowman placed a runaway advertisement describing him as about twenty-one, straight-limbed and likely, wearing a light-colored jacket, a beaver hat, and a blue coat with white metal buttons. Bowman believed Cicero had gone off with a rifleman to join the army. He offered ten dollars for his capture.

Reuben Colburn found Cicero in Cambridge, where Washington’s army was camped, and brought him back to Pownalborough. Colburn was in Cambridge to seek payment from Washington for boats he had built, so he may have had more than one reason to be there. An accounting from December 25, 1775, records his expenses for retrieving Cicero. It is the last time Cicero appears in the record.