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Conversations in Management

Leona Helmsley

Only the little people pay taxes.

This observation is best filed under; “famous last words.” Helmsley reportedly said it to her housekeeper in September 1983. Six years later she went to trial on 33 counts of tax evasion. Already dubbed The Queen of Mean, her attorney pleaded with the jury not to hold her personality against her. It didn’t work. She received a 16-year sentence though ended up being incarcerated for only 18 months. Still, it was a dramatic come-down for the haughty Leona Helmsley.

Helmsley was always good at self-promotion. The daughter of Polish immigrants, she began her career as the billboard model for Chesterfield cigarettes. Later she achieved substantial success as a real estate broker for tony New York City properties. She was in her early fifties and a veteran of two failed marriages when she met Harry Helmsley. Harry was New York’s premier real estate deal-maker in the era prior to Donald Trump and his properties included some of the city’s most fashionable addresses. He also owned a chain of high-end hotels. The glamorous Leona was a perfect match for Harry. Together they threw lavish, “I’m Just Wild About Harry” parties in their penthouse and, after the guests had arrived, would make a grand Fred Astaire and Ginger Rogers style entrance. Capitalizing on her socialite image, Leona took charge of the hotels and featured herself in a series of ads that announced, “It’s the only Palace in the world where the Queen stands guard.” Wags commented that the hotel employees in the background of these ads always appeared frightened. They probably were because Leona Helmsley really was—mean. She was legendary for her vicious temper, for firing employees over trifles and for generally terrorizing her staff. Despite her wealth, she also let contractors and vendors go unpaid and filed nuisance lawsuits with relish. The mean streak applied to family, as well. When her forty year-old son died suddenly, Helmsley promptly evicted his widow and her grandson from their house and sued to retain their furniture! It’s small wonder that the little people took so much pleasure at her comeuppance. The crowd actually jeered as she was led away from the court after her sentencing. But the greatest indignity was yet to come. Saturday Night Live found her an irresistible target and made her the subject of a long-running comedy sketch.

When Leona died—ten years after her husband—Donald Trump commented, “Harry loved being with her and the excitement she brought and that is all that really matters.” But is it? Leona Helmsley’s character flaws brought a good deal of pain to a good many people. It left her estranged from her family and—despite a frenetic social life—with few friends. As life closed in on her, she was principally surrounded by paid retainers—even her dog was gone (it was too mean). Her estimated net worth of $2.5 billion didn’t buy her any sympathy either. While she gave away millions to various charities and left the bulk of her estate to the Helmsley Charitable Trust, her obituaries all featured The Queen of Mean tag.

For those of us still in the land of the living, Helmsley’s passing is a reminder that we should consider our own legacy while we still have the chance to do something about it. It might also be a good idea to take a short-term perspective on this self-assessment. After all, we’re constantly moving on in one way or another. What will folks remember about you when you take a job somewhere else or retire? What would you like them to remember? Everyday provides another opportunity to burnish or tarnish your reputation. Which will you do today?

—Ebert