Daniel Drayton (Bordewich, 2006)

Drayton was of a rougher cut, with a large cleft chin, gloomy eyes, and brows that knotted over the bridge of his nose: it was a sad face, wrinkled and scored by more than two decades at sea. Strictly speaking, he was not an underground man, at least not in the way that [William] Chaplin was. He was a Philadelphia ship’s captain who desperately needed money. What [Chaplin and Drayton]  were planning was the biggest organized break-out of slaves in underground history thus far….Drayton’s life was one hard-luck story. He was born in poverty, in 1802, in New Jersey, not far from the mouth of the Delaware River. Taking to sea as a cook at the age of nineteen, after several miserable years in a sloop working the mid-Atlantic coast. On its second voyage, the sloop struck a snag near the mouth of the Susquehanna and sank in five minutes, its uninsured cargo a total loss. His next vessel sank off North Carolina with a cargo of coal and several of its crew. Another was blown ashore on Long Island, with a hundred tons of plaster. Still another was lost in a freak snowstorm, in Chesapeake Bay.