(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
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Year In Review:
For 2017, as of last week, Out of 1 Votes: 100% 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
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In 2011, Out of 19 Votes: 57.89% Annoying
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