A Watcher, Raleigh was assigned to the Immortal, Richard Sharkey, the captain of the merchant vessel, Perpetuity, in 1656. When he reported that Sharkey lost his head to Walter Reinhardt in 1662, he also requested to resign from his life at sea. The tribunal granted his request, and he returned to England for reassignment.
He had been educated as a scribe, and was well versed in English, French, and Latin. In 1663 he became part of Walter Graham's traveling theatre group. He was assigned to Duncan MacLeod, who was also part of the group until 1665. MacLeod left the group and Raleigh observed him till 1675.
From 1676 to 1686 he was assigned to Robert Montague. He retired in 1686.