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Harry Helmsley

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Entrepreneur

The Resume

    (March 4, 1909-January 4, 1997)
    Born in Manhattan, New York
    Real estate mogul
    Holdings included the Empire State Building, Helmsley Palace, the Flatiron Building, the Park Lane Hotel and the Carlton House Hotel
    Estimated net worth at his death: $1.7 billion
    Husband of Leona Helmsley

Why he might be annoying:

    He began sleeping with Leona while still married to his first wife, Eve Green.
    In a display of his cheapness, after he bought the New York Central Building and was contractually obligated to change the name, he went with New York General Building so he would only have to pay for two new letters.
    After Leona's son from an earlier marriage, Jay Panzirer, died, he unsuccessfully sued the estate to get reimbursed for the cost of transporting the coffin to the funeral.
    He also served Jay's widow, who was living at one of his properties, with an eviction notice, claiming he could no longer afford to let her live there for free.
    He was indicted along with Leona for tax evasion, but avoided any punishment when he was declared incompetent to stand trial due to encroaching senility.

Why he might not be annoying:

    He worked his way up from $12 a week office boy to broker to partner in a real estate firm.
    Unlike the obsessive Leona, he was known for his relaxed management style, commenting 'The more rules you have, the more problems you have.'
    He donated $33 million to New York Hospital (1986).
    One biographer said he 'towered over New York's real estate market just as the Empire State Building dominated mid-town Manhattan.'

Credit: C. Fishel


Featured in the following Annoying Collections:

Year In Review:

    For 2024, as of last weekly ranking, Out of 1 Votes: 0% Annoying
    In 2023, Out of 9 Votes: 66.67% Annoying
    In 2022, Out of 3 Votes: 100% Annoying
    In 2021, Out of 9 Votes: 77.78% Annoying
    In 2020, Out of 4 Votes: 100% Annoying
    In 2019, Out of 4 Votes: 50.0% Annoying
    In 2018, Out of 2 Votes: 50.0% Annoying
    In 2017, Out of 10 Votes: 50.0% Annoying
    In 2016, Out of 2 Votes: 100% Annoying
    In 2015, Out of 10 Votes: 60.0% Annoying
    In 2014, Out of 23 Votes: 43.48% Annoying
    In 2013, Out of 18 Votes: 50.0% Annoying
    In 2012, Out of 20 Votes: 65.00% Annoying
    In 2011, Out of 19 Votes: 57.89% Annoying