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James Colosimo

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Outlaw

The Resume

    (February 16, 1878-May 11, 1920)
    Born in Colosimi, Calabria, Italy
    Birth name was Giacomo Colosimo
    Italian-American Mafia boss
    Established the Chicago Outfit
    Empire built on prostitution, gambling and racketeering
    Nicknamed 'Big Jim' and 'Diamond Jim'

Why he might be annoying:

    He worked as a precinct captain and bagman for the Chicago political machine, developing the connections that helped him rise in organized crime.
    His first wife was a brothel owner and he expanded their empire into 200 houses of prostitution.
    He also ran a 'white slavery' ring, kidnapping women and forcing them into prostitution.
    He was responsible for bringing Al Capone to Chicago, hiring him as a bouncer/bartender at the Four Deuces brothel.
    He was denied a funeral in consecrated ground by the Roman Catholic Church -- not because he was a criminal, but because he was divorced.

Why he might not be annoying:

    He was a dapper dresser (hence, 'Diamond Jim').
    His legit nightclub, Colosimo's Cafe, was popular with Chicago bigwigs and visiting celebrities.
    He was a victim of extortion by the Italian Black Hand society (at least until he brought Johnny Torrio from New York to deal with them).
    When Prohibition started, he refused to get involved in bootlegging liquor, resulting in Johnny Torrio ordering a hit on him and taking over the Outfit.
    At his lavish funeral, the 53 pallbearers included several Congressmen, judges and city aldermen.
    The hit against him was featured in the first episode of Boardwalk Empire.

Credit: C. Fishel


Featured in the following Annoying Collections:

Year In Review:

    In 2022, Out of 3 Votes: 66.67% Annoying
    In 2021, Out of 6 Votes: 83.33% Annoying
    In 2020, Out of 10 Votes: 50.0% Annoying
    In 2019, Out of 16 Votes: 37.50% Annoying
    In 2018, Out of 17 Votes: 41.18% Annoying
    In 2017, Out of 18 Votes: 50.0% Annoying
    In 2016, Out of 10 Votes: 50.0% Annoying
    In 2015, Out of 15 Votes: 53.33% Annoying