The rediscovery of Peter Fleet’s will at the Massachusetts Historical Society provides an opportunity to examine the legacy of early America’s first Black newspaperman. Fleet provided a previously unrecognized connection between printed news and the enslaved community of Boston. As the enslaved typesetter of the Boston Evening-Post, he composed more stories of slave unrest than any newspaper in New England during his time at the press. Fleet’s labour in the print shop placed him at the center of communication of rumours of rebellion and freedom in the early British Atlantic. Fleet’s will may be the earliest known record of probate created by a Black slave in the English-speaking world, but his manuscript gains greater significance as evidence of Fleet’s long struggle to assert control over his life and labour at one of early Boston’s most influential newspapers.