Voting Station

Whitey Bulger

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Outlaw

The Resume

    (September 3, 1929-October 30, 2018)
    Born in Dorchester, Massachusetts
    Birth name was James Joseph Bulger, Jr.
    Served time for armed robbery and hijacking in the federal penitentiaries in Atlanta (1956-59), Alcatraz (1959-62), Leavenworth (1962-63) and Lewisburg (1963-65)
    Became an enforcer in South Boston's Killeen Gang
    Following a gangland war, joined the Winter Hill Gang
    Became head of the Winter Hill Gang following the arrest of boss Howie Winter (1979)
    Also served as an FBI informant
    Became a fugitive after being indicted for murder, racketeering, extortion, conspiracy and narcotics distribution (1995)
    Added to the FBI's 10 Most Wanted List (1999)
    Captured in Santa Monica, California (June 22, 2011)
    Charged with 19 murders; trial began June 12, 2013
    Found guilty of 11 murders and other racketeering-related crimes (August 12, 2013)

Why he might be annoying:

    He was first arrested, for larceny, at age 14, and before he left his teens he had added armed robbery and assault and battery to his rap sheet.
    While in the Air Force, he spent time in the stockade for assault and for going AWOL.
    He used his status as an FBI informant to get members of the Patriarca crime family busted, then moved into the resulting power vacuum.
    He ran New England's extortion, loansharking, bookmaking and protection rackets.
    FBI agent John Connolly tipped him off about his pending arrest (1995).
    After his status as an FBI informant was revealed, former crime associates began cooperating against him, leading to the discovery of secret graves of his victims and an additional 19 murder charges.
    When his wife got tired of life as a fugitive, he and his favorite mistress went on the lam together instead.
    When arrested in Santa Monica, he reportedly had 60 weapons and $800,000 cash in his apartment.

Why he might not be annoying:

    Growing up, his family lived in poverty after his dad lost an arm in an industrial accident.
    He (somehow) received an honorable discharge from the Air Force.
    According to associates, he forbade the drug dealers paying him protection from selling heroin or PCP and from selling to children.
    He inspired the character of Frank Costello (portrayed by Jack Nicholson) in the Oscar-winning film 'The Departed.'
    He was allegedly spotted at a showing of 'The Departed' in San Diego (2006).
    The property managers of the apartment building where he and his mistress were arrested said that they were ideal tenants who always paid the rent on time.

Credit: C. Fishel


Featured in the following Annoying Collections:

Year In Review:

    For 2024, as of last weekly ranking, Out of 7 Votes: 100% Annoying
    In 2023, Out of 11 Votes: 100% Annoying
    In 2022, Out of 10 Votes: 100% Annoying
    In 2021, Out of 28 Votes: 25.00% Annoying
    In 2020, Out of 21 Votes: 23.81% Annoying
    In 2019, Out of 9 Votes: 22.22% Annoying
    In 2018, Out of 127 Votes: 49.61% Annoying
    In 2017, Out of 13 Votes: 46.15% Annoying
    In 2016, Out of 10 Votes: 60.0% Annoying
    In 2015, Out of 23 Votes: 56.52% Annoying
    In 2014, Out of 28 Votes: 53.57% Annoying
    In 2013, Out of 263 Votes: 67.30% Annoying
    In 2012, Out of 18 Votes: 66.67% Annoying
    In 2011, Out of 117 Votes: 76.92% Annoying