Wednesday, June 22, 2011

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).


  1. I agree, Leona does look like Joker from Batman!! The whole windswept face is becoming ubiquitous these days!! Her lifestyle is a perfect example of the hedonistic and debauched lifestyle of the super wealthy! I do admire her love and dedication towards her pet!! At least some redeeming quality! Although who am I to judge :)

  2. Good grief what a biotch and how ridiculous to leave your dog so much money when there are thousands of charities and non-profits who need support! One thing that stands out from all my social work uni classes is "the rich get rich and the poor get poorer" which is extremely true when it comes to taxing.

  3. Haha this woman was just crazy. I agree that she looks like the joker Lol

  4. I remember Leona well. I also followed the trial and will never forget how much I hated her for that statement about paying taxes. As I recall she was ratted out by her long-suffering staff, which is just beautiful. Karma's a bitch.

    I actually stayed at the Helmsley Hotel when I was in NYC a few months ago; I kept imagining the face of Leona Helmsley until I realized I was actually imagining the face of Suzanne Pleshette playing Leona Helmsley in a made-for-tv movie. I think they gave Leona an undeserved gift by casting Suzanne.

  5. I'm waaay too young to remember this, but I remember hearing about it. What a strange life to live that you would be so alone you had to leave everything to a dog...
    PS looking at your mermaid parade pics, I really wish I had gone!!!

  6. People like her make me feel so sad, for having to co-exist on this planet. And as much as I'm trying to think that everybody has a place in the world and some use, I find it very hard to excuse her. And what a poor dog...What a waste of feelings, money, energy e.t.c. to end up like that.... That trial must have been something!

  7. She does look like Joker... jeez!

  8. Some character! I think this story shows all too well how people tend to get corrupted when they have too much power (financial or otherwise).

    That statement about taxes is disgusting, but I feel strangely gleeful that she made it because it's so blatant, it exposes this attitude that rich people should not pay too many taxes (because they are assumed to have worked hard and honestly for their wealth) for what it is - hard-hearted and selfish, failing to take into account the responsibility all citizens have towards their fellow citizens! Too bad this attitude remains influential in the US to this day...

    Sadly, the story also shows how permeated society was (still is?) by misogyny - stating that someone is simply "a bitch" is supposed to defend her, really? How would that guy have defended her husband? She was apparently an evil person, it's good that she went on trial (though the apparent glee people felt, while understandable, isn't something I fully accept)... but trying to explain her meanness as something intrinsically female, really? "Bitch" does exactly that, methinks.

    Also, it's amazing how well-groomed a dog can look given enough funding. What happened to all the money after Trouble died?

    I agree she looks a bit like the Joker. "Why so serious...?"
    Concerning your last comment, I must say I don't know - I'm certainly a person who takes life in general, and lots of its aspects, very seriously, loves to analyze and tends to over-think.... but I also have a joyous, light-hearted side, I love to tell funny anecdotes and make people laugh. I guess I should bring it out more on the blog, but it's difficult to gauge humor in written form.

  9. Wow. Never heard of her before. We of course have heard stories about rich eccentric americans leaving their fortunes to their pets, but not this one. It is sad ending your days alone, because you have been awful to others.

  10. Hadn't even heard of her ... but I do share the same thoughts as ambuji! :)

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  11. It really makes me sad, her attitude and behaviour. Why do people change like that when they have a lot of money!!! I feel sorry for the dog though, I don't really think having such a big inheritance made any difference to him whatsoever. After all dogs really don't care about luxury brands and such, all they want is one's real affection.


    Twitter - @ishrattrishna

  12. No worries, I was absolutely not offended! I too think it's good to take things seriously... though it certainly helps one's sleep if one can also just relax and have fun from time to time.

  13. i remember her always being in the news back in the 80's
    actually stayed in one of her boutique hotels in NYC in the 90's.
    she was a piece of work

  14. She does have a devious smile...I wouldn't trust her with anything.
    I kind of remember hearing about a lady who left money to her dog a few years back but not familiar with the history. I enjoyed reading this post.

  15. I think that there are many crazy people in the world that make the rest shine even better.

  16. what an interesting read. how funny that she was only nice to a dog. lol

  17. HAHAHAHA!! Omg that last comment! SHE TOTALLY DOES!!

    Seriously, what a horrible person. I am glad that she got busted and lived the rest of her life alone but still. She should have been locked up for longer or something.

  18. Wow, what an interesting story. I hadn't heard but then again I wasn't living here then. So what happened to the money after the dog died? I am curious? You would think she would donate it if she had no one...

  19. She DOES look like the joker. I remember Jack Nicholson with that iconic joker makeup and that diabolical smile.

    People like Leona make me sad. I do see many people like her (to a lesser extent of course). People believe that money, power, education, or socioeconomic status give them the right to powertrip. In that sense, I am thankful for the setbacks in my life as they are humbling experiences. My favorite athlete (and crush!) is Roger Federer. He's arguably the greatest tennis player ever, but he's also known as one of the nicest guys on tour. His motto in life is "It's nice to be important, but it's important to be nice." Cheesy, but I try to live by that too.

  20. I wouldn't be surprised if the way this movie's version of the Joker was purposedly patterned after her. The filthy rich are indeed different kinds of (un)human beings... ah, such is life!

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  21. Ew, she does look like trouble. The "little people" comment sickened me. I guess she didn't realizing she was saying to the person, "You are a little person and do not matter to me." She deserved to die miserable and alone.

  22. She sounds like a total badass. Is it any surprise that I am in love with her??
    Twitter: @GlamKitten88

  23. Whoa. I had heard her name before but had no idea who she was til I read this. What a sad and pitiful wasted life. Even when not in prison...she still figuratively was.

    All the same, I had to LOL at Bonnie's comment!

    It's sad that her dog would get death threats, though. It wasn't his fault he had such a terrible person for an owner. He's probably the only one in the whole world who ever thought highly of her. What happened to the fortune?

  24. Oh...I just clicked on the article you linked to and saw the fortune went to charity. How utterly unexpected.

  25. I remember seeing on tv long way back when she left the dog the money. Everyone was amazed. A millionaire dog.
    It's a shame that after all she went through (Leona) she did not make adjustments in her final years and became a better person. I guess some people are bitches until their death. How very sad.
    I hope I never have the money that turns people this way.
    Anyways as the germans say "the last shirt has no pocket".
    I am also wondering if my maltese dogs Vanilla and Marshmallow could be related to Trouble, maybe they are distant cousins and they can inherit from him... :)

  26. This is such an interesting story! I had no idea!
    What happens to the fortune now? does it sort of become the states money?

    As for Ms still seems unfair that she ended up living a pretty decent life regardless of her sentence. I get that the prison systems are crowded, but it seems a bit ridiculous no?

    Thank you for enlightening me!

  27. That's it - The Joker! I've always thought the same. Interesting information about the case. I can't believe Trouble received death threats - OMG.

    I've been reading through your posts -- I love your writing style. And all the fabulous photos and outfits too!