Born in 1891 in New York City the 4th of seven children to an Irish immigrant family, Michael was raised on the lower east side, and by the time he was ten, he was running numbers for the Irish mob. Crime was lucrative for a boy of his age. As he grew so did his place in the mob, and the money got better with his age and responsibility.
By the time Michael was twenty-one, he had killed two rival gang members trying to strong-arm a business that paid protection to his mob. This promoted him to Paddy Ryan's inner circle. The high life.
Unfortunately, the First World War interrupted his rising career when Michael was drafted into the Army, where he would hone a part of his craft, killing.
Upon his return, things had changed, and not for the better. Paddy Ryan was dead and the gang disbanded and Irish gangsters were not well received. Prohibition loomed, organized crime began to emerge, slowly at first, but by mid-1920 things were in full swing.
Again, Micheal was involved in a shooting scrape and wisely fled to Florida where he found the climate and opportunities were warmer for a man from New York. Michael "Nails" O'Rourke fit right in.
Working as an independent, with several concrete alliances, he built a strong reputation as a smuggler, muscle and trusted bodyguard. It was 1923 and life was good. The money came easy, which he liked, but he was not fond of Miami, or big cars. With connections and cash and a move south to the Keys he bought a Hodgdon Liberty commuter yacht with a cruising range of 550 miles which would allow him easy travel to Havana, or Bermuda, or any of the islands he might have the occasion to go.
This allowed for a bit of smuggling, here an there, or when needed lucrative, discrete, transportation for an associate who needed to be out of the country for whatever reason. It was a living.