The Queen Of Mean

Leona Helmsley was a New York billionaire famous during the 1980's.  Leona went to prison at the end of that decade and she died in 2007.  In her Will, Leona left her beloved Maltese dog named Trouble a bequest of $12 Million.  Trouble died a few months ago at 12 years of age, after a life of pampering and luxury.  I thought I'd tell you a little about their story.

Leona and her husband Harry were wealthy real estate developers.  In the 1980's, their empire of New York City buildings was worth $5 Billion.  That's 5,000 Million dollars.  One of my earliest clients used to be a business partner with Harry; both he and the Helmsleys were slippery characters.

Leona was active in her husband's real estate business and she had a horrible reputation.  People described her as tyrannically cruel and selfish.  She fired people cavalierly for no reason and enjoyed making people beg for their jobs.  In the 1980's, she was widely known in New York as "The Queen of Mean."

Leona became infamous for a remark she made to her housekeeper.  Impressed at Leona's wealth, the housekeeper observed that Leona must pay a lot in taxes.  Leona's response was: "We don't pay taxes. Only the little people pay taxes."  That comment captures Leona's attitude of condescension and entitlement.

Leona and Harry used contractors to work on their personal homes while billing the expense to their company.  It was a way to cheat the government out of taxes.  In 1988, Leona and Harry were charged with tax evasion by then-prosecutor (and later-Mayor) Rudy Guiliani.  Harry was too ill to stand trial, so Leona went on trial by herself.  The trial was a big event in New York at the time.  I followed it closely.

There was a long parade of people happy to slam Leona for her history of insults and bad behavior.  The most fascinating part of the trial was her lawyer's closing argument.  Addressing the jury, he said -- and I'm not making this up -- that his client Leona "is a bitch."  It was impossible for him to credibly argue otherwise.  He tried to explain that while Leona was a lousy person, she was not a criminal.  He tried to separate the overwhelming attacks on her character from the legality of her behavior.  The effort failed.  The jury found her guilty.

Leona was sentenced to 16 years in prison but was released after only two.  The end of her life was spent alone.  Harry died and Leona had no friends.  She devoted her attention on Trouble and left him a fortune.  After Leona died in 2007, Trouble had full-time bodyguards because -- and, again, I'm not making this up -- he received death-threats.  People threatened to kill Trouble simply because they hated Leona so much.

What do you think of this story?  Oh, and I always thought Leona looked like The Joker, played by Jack Nicholson in "Batman" -- released that same year as Leona's trial (1989).