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 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 (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.