Leona Helmsley: 'The Queen of Mean'

After dropping out of school, Leona claimed she worked as a Chesterfield cigarette ad model. However, her claims have largely been unsubstantiated. To date, there is no evidence that anyone under the various pseudonyms Leona used ever posed as a model for the cigarette company. The only known relation Leona had to Chesterfield cigarettes was her insatiable desire to smoke. Leona was a chain smoker, inhaling several packs a day. It was a habit that would continue well into her adulthood.

At the age of 16, Leona alleged to have enrolled into New York 's Hunter College, although there is no record of her having ever attended the school. She claimed to have dropped out after two years of study. Her focus was purportedly shifted from school towards a new interest, a young attorney ten years her senior named Leo E. Panzirer.

In 1938, following a brief courtship Leona and Panzirer married. Four years into the marriage the couple welcomed the birth of their first child, Jay. Not much is really known about the marriage except that shortly after their son's birth, the relationship began to fall apart. During the late 1940s the couple separated then eventually divorced.

Following her divorce from Panzirer, Leona went to work as a secretary for a garment industry executive named Joseph Lubin. Soon after, Lubin began to display an interest in her. The two dated and before long they were married. The relationship would prove to be as unsuccessful as her first marriage. After a few years the marriage ended in divorce. However, the relationship was rekindled again shortly thereafter and the couple decided to give married life another try. They married a second time but after five years, the relationship ended again in divorce.

At the age of forty-two Leona found herself with no job, a grown son to feed and no college education but she refused to let her circumstances deter her. Leona was considered a tough and intelligent woman with a great deal of ambition. She was determined to work hard to fulfill her dreams of one day becoming a huge success. She knew she would likely have to start small and work her way up the socio-economic ladder before she could obtain what she believed she deserved.

Following the breakup of her marriage she temporarily worked at a sewing factory before landing a secretarial job with a real estate firm known as Pease & Elliman. Two years into her job with the firm there was a shift of ownership, which proved to be Leona's lucky break. It would forever change her life.

After the change-over, Leona convinced her new bosses to give her a company license to sell real estate, believing she could outsell the other brokers employed by the firm. It was from that moment that Leona found her true talent as a saleswoman. Leona started with a small clientele, proving that she had an aptitude for selling property. Before long, the firm assigned her to sell cooperative apartments units and condominiums (condos) in more upscale residential areas, a position in which she excelled. 

According to Hammer, Leona became vice president of the real estate company after several years, which earned her "a salary and commission in six figures" and allowed her to buy a luxurious pent house on 55^th Street in Manhattan. He further stated that in the late 1960s Leona expanded her interests when she established a subsidiary division called Sutton and Towne Residentials, where she acted as president and sold cooperatives and condos in one of Manhattan 's wealthiest districts. She had come a long way in a short period of time, yet her newfound success wasn't sufficient enough to satisfy her ambition. Leona set about accomplishing her goals of becoming successful on a much grander scale.