Harry Helmsley

Harry Helmsley
Harry Helmsley
Born	4 March 1909 (age 117); Manhattan, New York City, U.S.
Died	4 January 1997 (aged 87); Scottsdale, Arizona, U.S.
Occupation(s)	Real estate billionaire, hotelier
Known for	Ownership of Helmsley-Spear, Empire State Building, Helmsley Building, various New York hotels

Harry Brakmann Helmsley (March 4, 1909 – January 4, 1997) was a prominent American real estate billionaire whose enterprise, Helmsley-Spear, emerged as one of the nation’s largest property owners, holding iconic assets such as the Empire State Building and numerous distinguished hotels throughout New York. His marriage to Leona Roberts, famously known as the "Queen of Mean," eventually led to allegations of fraudulent accounting and tax evasion; Harry was considered too ill to undergo trial, whereas Leona faced fines and imprisonment.

Early career

Helmsley was born in Manhattan and grew up in The Bronx, leaving Evander Childs High School without completing his diploma. Lacking resources for higher education, he began his career as an office assistant at Dwight, Voorhis & Perry. His aptitude propelled him to partner status, and in 1938 he acquired the company, renaming it Dwight, Voorhis & Helmsley. Initially, his investments targeted smaller yet lucrative properties located in less prosperous neighborhoods of New York.

Notable properties and companies

In 1954, Helmsley purchased the Lincoln Building, a significant office tower on 42nd Street. The next year, he acquired Leon Spear's real estate management firm, which led to the creation of Helmsley-Spear.

By 1961, Helmsley had secured ownership of the Empire State Building, then the tallest building globally despite concerns over its upkeep expenses. His portfolio also encompassed prominent office buildings such as the Helmsley Building at 230 Park Avenue, the Graybar Building, Flatiron Building, Fisk Building, Toy Center, and 1350 Broadway. Residential properties under his control included Park West Village, Tudor City, Fresh Meadows in Queens, and Parkchester in the Bronx. Industrial assets featured the Starrett–Lehigh Building and Bush Terminal.

Starting in the 1970s, Helmsley extended his reach into hospitality by acquiring hotels like the Helmsley Windsor Hotel and Park Lane Hotel, as well as developing the Helmsley Palace adjacent to the Villard Houses on Madison Avenue.

By 1980, Helmsley-Spear employed approximately 450 individuals. In 1964, he also acquired Brown Harris Stevens, a leading residential brokerage managing elite co-op buildings along Park Avenue, Fifth Avenue, and Central Park West. At its sale in 1995, Brown Harris Stevens oversaw management of 128 buildings.

Helmsley was a commanding figure in Manhattan’s real estate market and beyond; during the early 1970s he developed The Palace on Brickell Avenue in Miami—a luxury condominium tower comprising 254 units.

His achievements were largely attributed to exceptional salesmanship, effective delegation, and a unique acquisition approach: obtaining long-term fixed-rate mortgages during economic downturns and purchasing properties outright when interest rates were favorable—a method now widely adopted in real estate investment.

Marriage to Leona

In 1938, Helmsley married Eve Ella Sherpick Green, a widow. After their divorce in 1971, he wed Leona Roberts in 1972, who was at that time a vice president within one of his companies. Known for her assertive management style and labeled the "Queen of Mean," Leona introduced an opulent lifestyle that sharply contrasted with Harry’s previously modest habits. The couple resided in a penthouse at their own Helmsley-owned Park Lane Hotel on Central Park South and expanded their hotel ventures beyond New York with large-scale developments.

Their growing portfolio included The Helmsley Middletowne Hotel, New York Helmsley Hotel (also known as New York Harley), Helmsley Windsor Hotel, St. Moritz (now operating as the Ritz-Carlton), Carlton House hotels, Harley Hotel chain, and ownership of The Helmsley Building in New York City.

In recognition of his significant contributions to New York City, Harry was honored with The Hundred Year Association of New York's Gold Medal Award in 1980.

Their premier project was the 50-story Helmsley Palace Hotel located on Madison Avenue at Fiftieth Street, which opened in 1980 as one of Manhattan’s most luxurious establishments. However, this venture also marked the beginning of financial troubles and legal challenges connected to Leona’s extravagant spending habits that escalated construction expenses. Investigations revealed they had subcontracted work to affiliated companies at inflated rates. In 1988, both were charged with major tax evasion offenses involving falsified accounting records; Harry was found medically unfit for trial while Leona served an eighteen-month prison sentence accompanied by substantial fines.

Death

At the age of 87, Helmsley passed away due to pneumonia in Scottsdale, Arizona. He bequeathed a business empire worth approximately $5.5 billion to Leona. Initially interred at Woodlawn Cemetery in the Bronx, his remains were subsequently relocated to Sleepy Hollow Cemetery in Sleepy Hollow, New York.

In popular culture

The relationship between Helmsley and Leona was portrayed in the 1990 television film Leona Helmsley: The Queen of Mean, featuring Lloyd Bridges as Harry and Suzanne Pleshette as Leona. Pleshette received nominations for both an Emmy and a Golden Globe for her performance.

External links

American National Biography Listing for Harry Helmsley