His wife, Leona Helmsley — notoriously called the "Queen of Mean" — was convicted in 1989 on federal charges of tax evasion in a celebrated trial. Harry had been indicted along with Leona, but it was determined that he was far too ill physically to stand trial and too weak mentally to be capable of assisting his attorneys in his own defense, one of the legal standards which allows crimes to go unprosecuted on the grounds of mental defect of the defendant.
In 1980, Mr. Helmsley received The Hundred Year Association of New York's Gold Medal Award "in recognition of outstanding contributions to the City of New York."
Also in 1938, he married Eve Ella Sherpick Green, a widow.
In 1955, he acquired business competitor Spear & Company, which became Helmsley-Spear and expanded his holdings in lower Manhattan. He purchased real estate firm Brown Harris Stevens, which brought him into rental and cooperative apartment sales and management; it was also where he hired Leona Roberts in 1970 as senior vice president.
He divorced his first wife Eve in 1971 and married Leona in 1972.
Harry Helmsley died of pneumonia 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, NY