Earning his “Flag” under Captain Bartholomew Roberts, Fenn was born in England (date Unknown). His fierce attitude in combat earned him his first command (21-Gun Frigate, “Morning Star”). Preying on both English and Spanish Merchants – his ship took 4 on his first “cruise”. Unfortunately, Fenn would lose a large number of his crew (and ship) – to a hurricane off of The Grand Cayman Islands. In addition, Fenn lost his right hand (ripped off by a splintering Bow Sprit). Later “hooked”, Fenn secured another ship The “Good Fortune”. Going “back to business”, Fenn was intercepted by The Royal Navy attempting to take 3 Merchant Ships. Able to outrun the Warships, he beached his ship on the Island of Tobago. Running for the “safety” of the Jungle, Royal Marines landed and captured him (and some of his crew). Fenn and his surviving crew were hung a month later.