Jack was born just outside Bath in 1750 to humble yet innocent beginnings. He worked as a child and by the age of twelve was working as a postilion which paved the way for him to take various coachman jobs, eventually leading him to London. Jack felt alive in the busy metropolis. He was young, good looking and there was plenty in the city to keep him entertained...especially when it came to fashion. Jack soon earned himself the nickname of Sixteen-String Jack from his trademark pants which had eight strings hanging down each leg, each one a different color. When Jack couldn't keep up his fashion expenditures with his wages he turned to pickpocketing which evolved to highway robbery, which he found he was quite good at.
Fashionable Jack's new career allowed him the comforts of attending balls, picking up women, and of course buying all that wacky designer clothing. Jack was arrested several times but always seemed to get off due to lack of evidence. He once took the stand in front of Magistrate John Fielding wearing a bouquet of flowers blooming from the breast of his coat and accessorized his shackles with some comely blue ribbons. Next time he was in court for being caught breaking into a woman's window into her bedroom (was it the future Lady Lade, I wonder?) but was acquitted due to the fact that she was expecting him but had fallen asleep. A week later Jack had waltzed into an establishment, in a scarlet coat, silks stockings, and a lace hat and announced that he was a highwayman and proceeded to pick fights with everyone until a brawl broke out. I think it safe to say Jack was not just a highwayman but a macaroni.
The twenty-four year old robbed his last victim in 1774 when he was tried for heisting Princess Amelia's Chaplain. Jack showed up to the trial in a pea-green suit, fully expecting to get off due to lack of evidence again. He was quite shocked when he received the guilty sentence. Still, what's a rake to do? Make the most of the situation is the answer. He held a farewell dinner in jail with seven lovely ladies and when he arrived at Tyburn he joked with his executioner and danced a jig before his last drop.