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Havey Bailey

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Outlaw

The Resume

    (August 23, 1887-March 1, 1979)
    Born in West Virginia
    Known as 'the Dean of American Bank Robbers'
    Stole between $3-5 million during his career (1920-33)
    Served time in Leavenworth (1933-34,1946-60), Alcatraz (1934-46), Seagoville Federal Correctional Institution (1960-61) and Kansas State Prison (1961-65)

Why he might be annoying:

    Before becoming a bank robber, he was muscle for the Chicago mob.
    He masterminded the robbery of the Denver Mint in which a guard was killed (December 18, 1922).
    While on the lam, he took refuge at a farm owned by the parents of Machine Gun Kelly's wife, ignoring a warning from another outlaw not to linger because the place was too 'hot' (thanks to Kelly's recent kidnapping of an Oklahoma oil baron).
    A few days later, a dozen FBI agents descended on the farm and he was literally caught napping (August 12, 1933).

Why he might not be annoying:

    He served with the Army in World War I.
    During an escape from Kansas State Prison (June 1, 1933), he convinced his fellow escapees not to kill their hostage, Warden Kirk Prathers. (He even gave Prathers $5 for cabfare home.)
    The FBI agent who woke him from his nap dared him to go for his gun, to which he calmly replied, 'I'm not crazy.'
    He played no role in the kidnapping of oilman Charles Urschel but got a life sentence for it, because he was in possession of $700 of the ransom money, which Machine Gun Kelly had left for him to pay off an old debt.
    Upon his release from prison he said, 'The main lesson is that crime don't pay. You have to pay for it.'

Credit: C. Fishel


Featured in the following Annoying Collections:

Year In Review:

    For 2024, as of last weekly ranking, Out of 3 Votes: 66.67% Annoying
    In 2023, Out of 10 Votes: 40.0% Annoying
    In 2022, Out of 3 Votes: 66.67% Annoying
    In 2021, Out of 11 Votes: 72.73% Annoying
    In 2020, Out of 11 Votes: 36.36% Annoying
    In 2019, Out of 23 Votes: 34.78% Annoying
    In 2018, Out of 9 Votes: 33.33% Annoying
    In 2017, Out of 10 Votes: 40.0% Annoying
    In 2016, Out of 14 Votes: 57.14% Annoying
    In 2015, Out of 9 Votes: 55.56% Annoying
    In 2014, Out of 22 Votes: 50.0% Annoying
    In 2013, Out of 19 Votes: 63.16% Annoying
    In 2012, Out of 13 Votes: 61.54% Annoying