Harry Brakmann Helmsley 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 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
Henry 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 early stages 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. on Park Avenue in New York City
Notable properties and companies
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. Other notable New York office properties that Helmsley owned during his career included the Helmsley Building, the Graybar Building, the Flatiron Building, the Fisk Building, the Toy Center and 1350 Broadway. He also invested in large residential properties including Park West Village on Manhattan's west side, Tudor City on the east side, and in Fresh Meadows in Queens and Parkchester in the Bronx. Industrial properties included the Starrett-Lehigh Building in Manhattan and Bush Terminal in the Bronx. During the 1970s and 1980s, Helmsley began investing in hotels. Among his holdings were the Helmsley Windsor Hotel, the Park Lane Hotel and the Helmsley Palace, which he built behind the Villard Houses on Madison Avenue between 50th and 51st Streets. In addition to Helmsley-Spear, which had 450 employees by 1980, he also owned Brown Harris Stevens, Inc., a residential brokerage firm. Helmsley bought Brown Harris Stevens in 1964. In addition to its high-end residential brokerage business, the company managed residential buildings, including some of the most prestigious co-ops on Park and Fifth Avenues and Central Park West. When Helmsley sold the business in 1995, the company managed 128 buildings. Helmsley became known 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.
Marriage to Leona
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, and she demanded a luxurious lifestyle, quite unlike the modest private life he had been living until 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, The Helmsley Windsor Hotel, the St. Moritz, 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.
