Born in 1702 in Mevagissey Cornwall the son of wealthy farmers. Many assume that the nickname Swilling Billy came from his ability to consume prodigious quantities of grog and remain in an upright position. However this nickname dates back to his youth on his parents farm where his job was to tend the large herd of pigs and he was responsible for making up their pig swill.. He thought he had escaped the somewhat onerous name when he joined the Navy…… until he bumped into an old friend from Mevagissey in a tavern who greeted him as Swilling Billy and his crew mates never let him forget it from that moment on.

At the age of 14 he joined the Royal Navy and sailed under Admiral Sir George Byng on HMS Barfleur. Rising to the rank of 1st Lieutenant, he gained a reputation as a fearsome swordsman and a fine marksman. He distinguishing himself at the battle of Cape Passaro near Sicilly on August 11th 1718 by leading a boarding party which captured the San Luis a 64 gun Spanish ship of the line.

However, what looked set to be an illustrious naval career was cut short when he was caught in a very compromising position with the admirals daughter. He soon found himself ensconced in the naval wing of Bodmin Goal awaiting court martial on a trumped up charge.

While there he made the acquaintance of Mad Paddy O'Toole, who was a fearsome Irish pirate who occupied the next cell. Between them they hatched a cunning plan and managed to make their escape. In the process they amazingly defeated 6 armed guards by using only a slops bucket and O'Toole's wooden leg as weapons. They made it across Bodmin Moor and met up with some of O'Toole's acquaintances at Sennan Cove and that is where Swilling Billy's Piratical career began.

He then spent several years jumping from ship to ship until he eventually signed on as crew with Captain Hogarth on the good ship “Lavender” owned by Lady Rose Wylde. He was quickly promoted to Captain of the “Lavender” after Captain Hogarth lost his wits to the pox and was forcibly retired. Soon after, Billy became Commander of Lady Rose's fleet of 5 ships. Some say his rapid promotion was more to do with his capabilities in Lady Rose's boudoir than with his abilities as a seaman but nobody dared question Lady Rose's wisdom in this matter. (at least not in her or Billy's presence anyway).

Lady Rose's fleet were referred to as Merchant ships in polite circles but they were in fact highly armed pirate ships which prayed on any unsuspecting Spanish merchantmen they came across. In fact, some less than charitable people say that the only thing these so called “Merchant” ships ever traded with anyone was cannon balls. For this reason the Royal Navy turned a blind eye to their activities and also failed to notice that the fleets commander was in fact an ex Navy deserter and a fugitive from Bodmin Goal.
The Hay day of Lady Rose's fleet was from 1739 to 1744 when England was continually at war with Spain and France and there were rich pickings for any privateer and Lady Rose and Swilling Billy made the most of this situation. Capturing 5 Spanish merchantmen, sinking 3 Spanish and 1 French Navy ships of the line and looting 35 more merchantmen over a period of 5 years. In his spare time, Billy aslo had a habit of sailing with his good friend Captain Nathaniel Blackheart on his many and extensive piratical expeditions.

They retired from Piracy in 1749 and the fleet which was beginning to show it's age was sold to another privateer. Lady Rose and Billy settled into a peaceful retirement and were frequent visitors to The Mermaids Tail (a tavern owned by Lady Rose.)

Even today in the tavern, (now renamed and extensively modernised) they still talk in hushed tones about the exploits of Lady Rose Wylde and Swilling Billy Flynn. Some even say if you go down to River Street in Mevagissey…….in the wee small hours you can still hear Billy playing his squeeze box and singing love songs to Lady Rose.