His early childhood was spent among the city’s immigrant Irish population, where he relied upon an established migrant Irish network to further his career in organised crime.
Madden grew up on the streets of New York, where he learned how to use blackjacks, brass knuckles, baseball bats, pipes, and knives, including the stiletto. By the age of 21 years old, Madden had become the leader of a feared New York street gang known as the Gopher Gang. He earned the nickname, "The Killer" for getting away with two brazen murders. On September 6, 1911, he shot dead a gang member of the rival Hudson Dusters in the heart of Dusters' territory around 30th Street. In February 1912, Madden was on a crowded street trolley, arguing with a store clerk named William Henshaw about a woman.