Leona Helmsley – Helmsley hotels
She said taxes are for little people. Then she paid a big price.
New York hotel and real estate magnate Leona Helmsley was renowned as the “Queen of Mean” for her tyrannical treatment of her employees, which made her prosecution all the more delightful.
In 1989, she was convicted on tax evasion, conspiracy and mail fraud charges.
She was prosecuted by none other than Rudy Giuliani, who had to be pardoned himself for trying to overturn the 2020 election. But back in the day he was a respected U.S. attorney.
Helmsley’s housekeeper famously testified that she had said, “Only the little people pay taxes.’”
Appropriately, Helmsley’s prison sentence began on tax day, April 15, 1992. She served 21 months and then retreated to a life of isolation with her dog, Trouble, a Maltese.
When her husband Harry died in 1997, Helmsely inherited his $5 billion empire, which included the Helmsley hotels, the Helmsley Palace and the Empire State Building.
A 1990 TV movie, “Leona Helmsley: The Queen of Mean,” dramatized the story of her life. Her legacy is a study in how someone can be so rich and yet so cheap and petty.
She once stiffed a contractor out of $13,000. When she was informed that the contractor had six children to support, she replied, “Why didn’t he keep his pants on? Then he wouldn’t need the money.”
Celebrity criminal defense attorney Alan Dershowitz called Helmsley “boring and rather stupid.” He told the New York Post she once had a fit right in front of him over a tiny splash of tea on a saucer at her hotel. She slammed the dishes on the floor. “Now clean it up and beg for your job,” she said to the waiter.
Helmsley died with few friends and was reportedly estranged from her grandchildren.
She left her dog a $12 million trust fund, though it was later reduced to $2 million, still making Trouble one of the richest dogs in history.
Despite her own moral flaws, she demanded honesty from those around her.
“I’m a very firm believer that a liar is a cheat and a thief and a crook,” she said in a 1990 interview with Playboy. “I don’t like liars. I never lie. I always told my own child, ‘If you murder somebody, tell me. I’ll help you hide the body. But don’t you lie to me.’”