He was part owner of the Star and Garter, a popular Sixth Avenue saloon, and was a longtime political organizer and "fixer" for Tammany Hall.
He was also involved in one of the longest bare-knuckle boxing prize fights when he defeated "Australian Kelly" after a near-three and a half hour bout at Island Pond in 1860.
He was a choir boy at St. Patrick's Church and was strongly encouraged to pursue religious training, and for a time considered entering the priesthood, but eventually became dissatisfied and left the school to work for underworld figures Ben Wood and Zachariah Simmons, both controlling the policy racket and illegal gambling in the city.
[4] He became deeply involved in illegal gambling, having mixed success with running faro banks throughout the city, and traveled the United States for almost 20 years becoming one of the most widely recognized sportsmen in the country.
This establishment became very popular in the area however, the following year, he was arrested by Captain Alexander "Clubber" Williams and charged with keeping a "disorderly house".
On January 22, he left his home to ride with a friend and returned seriously ill. Two physicians were called, Dr. Loomis and Sass, but were doubtful that he would recover.