Saggyboots Sullivan's career in illicit activities began young, shaving profane language on royal colonial livestock. This drew the ire of government when a paper published the headline, "Colonial Governor Eats 'Bawdy Lewdster'". From that Sullivan earned an arrest warrant and the governor, a new nickname. After sailing with other crews, how he came to captain the crew Bone & String is unknown, especially if you ask them.

Kevin "Saggyboots" Sullivan has been a performer all his life, first performing as "Baby Jesus". The road from Lord and Savior to piracy has included Shakespeare, musical theater. historical re-enactment, vocal recitals, a few bands, work as a singer/songwriter and a stint as Dora the Explorer.