Harry Helmsley

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Harry B. Helmsley
Born March 4, 1909
Died January 4, 1997(1997-01-04) (aged 87)
Nationality United States
Occupation Real estate developer
Net worth Increase US $6 billion
Spouse(s) Eve Ella Sherpick Green (divorced)
Leona Rosenthal Roberts (m. 1972)

Harry B. Helmsley (March 4, 1909 – January 4, 1997) was an American real estate billionaire whose company, Helmsley-Spear, became one of the country’s biggest property holders, owning the Empire State Building and many of New York’s most prestigious hotels. From humble beginnings, Helmsley moved up in property through natural salesmanship, a willingness to delegate, and shrewd acquisition policies that were ahead of their time. His second marriage to Leona Roberts (“Queen of Mean”) led to charges of false accounting and tax evasion as well as a celebrated trial, where Harry was judged too frail to plead, but Leona was fined and jailed.

Early career[edit]

Henry Brakman Helmsley was the son of Henry Helmsley, a wholesale dry goods buyer, and the former Minnie Brakmann. He was born in Manhattan and brought up in the Bronx, attending Evander Childs High School, where he did not graduate. The family could not afford a college education, but his grandfather got him a job as an office boy in a real estate firm, Dwight, Voorhis & Perry, where he showed a keen talent for the business and was made a partner. In 1938, he bought the firm, renaming it Dwight, Voorhis & Helmsley. In the first half of his career, his portfolio consisted mainly of smaller properties in less-affluent parts of New York City, though it was extensive and highly profitable.

The ornate facade of the Helmsley Building on Park Avenue in New York City

Prestige property[edit]

In 1954, Helmsley bought the Lincoln Building, a major office skyscraper on Forty-second Street. A year later, he bought a real estate management company owned by Leon Spear, and the firm became known as Helmsley-Spear. In 1961, he bought the Empire State Building—then the tallest building in the world—against warnings that the maintenance costs would be too high. Presently, these would be joined by the Graybar, Fisk, and Flatiron buildings, as well as major residential developments. By then, Helmsley was classed as the most influential real estate magnate in the city. His success was attributed largely to a gift for salesmanship, a willingness to delegate authority, and a less-usual acquisition policy of long-term fixed-rate mortgages during a slump and cash purchases when interest rates were low. This policy has since become standard in real estate.

Living and working with Leona[edit]

In 1938, he had married a widow, Eve Ella Sherpick Green. In 1971, he divorced her and the next year married Leona Roberts, vice-president of one of his many companies. She was a high-profile manager, dynamic but abrasive (“Queen of Mean”), and she demanded a luxury lifestyle, quite unlike the modest private life he had been living up till then. Basing themselves in a penthouse in the Helmsley-owned Park Lane Hotel on Central Park South, they moved into hotel construction and operation on a big scale, diversifying beyond New York for the first time, to many other big centres. Their portfolio included The Helmsley Middletowne Hotel, the New York Helmsley Hotel (also known as the New York Harley), The Helmsley Windsor Hotel, the St. Moritz (now the Ritz-Carlton), the Carlton House hotels, the Harley Hotel chain and The Helmsley Building in New York City. In 1980, Harry received The Hundred Year Association of New York's Gold Medal Award "in recognition of outstanding contributions to the City of New York."

His crown jewel was New York's 50-story Helmsley Palace Hotel on Madison Avenue at Fiftieth Street. The hotel opened in 1980 to great fanfare and soon became known as the city's most elegant venue. However, it marked the beginning of financial and legal troubles that would dog the marriage until Harry’s death. Partly due to Leona’s extravagant plans and frequent demands for changes, the cost of the building skyrocketed, and it was proved that they had contracted some work out to their own subsidiaries at inflated prices. In 1988, they were also charged with major tax evasion based on false accounting. By this time, Harry was judged too frail to plead but Leona served 18 months in prison, in addition to being heavily fined.

The mausoleum of Harry Helmsley


Helmsley died of pneumonia at age 87 at a hospital in Scottsdale, Arizona, and left all of his empire ($5.5 billion) to his wife, Leona. His remains were initially entombed at Woodlawn Cemetery in the Bronx, New York, but later moved to Sleepy Hollow Cemetery in Sleepy Hollow, New York.[1]

In popular culture[edit]

Helmsley's marriage to Leona was dramatized in the 1990 TV movie Leona Helmsley: The Queen of Mean, which starred Lloyd Bridges as Harry and Suzanne Pleshette as Leona. Pleshette was nominated for an Emmy Award and a Golden Globe Award for the portrayal.[2]


  1. ^ Lombardi, Kate Stone, "COUNTY LINES; Why Leona Buried Harry Not Once, But Twice", The New York Times, April 23, 2006
  2. ^ Leona Helmsley: The Queen of Mean on IMDb

External links[edit]