Leona Helmsley’s will

I’m not a fan of Leona Helmsley; among other traits that earned her the title of “Queen of Mean,” she sued her dead son’s estate, financially wiping his widow out with legal fees.

But one has to have sympathy for what’s happening to her will. Estranged from her four grandchildren, she left $10 million each to two of them, and disinherited two others. Those two sued, and successfully extorted $6 million each in a settlement. She left a small fraction more of her fortune for her dog, and a court sliced it substantially (though the dog is unlikely to mind). The remainder of Helmsley’s billions will go into a trust; Helmsley left vague instructions that it be used to help dogs, but it appears that the Helmsley trust is likely to become a candidate for cy pres and the personal charitable preferences of the trustees; the New York Times describes Judge Renee R. Roth as “flexible,” though one suspects that those who write wills and trust instruments would prefer judges to be inflexible so that it is their wishes, rather than the judges’ wishes, that are being observed. (Helmsley has herself partly to blame for not writing a clearer trust.)

Separately, I was interested to learn that Helmsley’s income tax conviction was questioned by her attorneys Alan Dershowitz and Robert Bork. Dershowitz describes his former client uncharitably, so watch what you say around him.

Update to the anecdote about the dog (named Trouble) being left millions: one of Trouble’s bite victims (there were apparently several) has suggested she might sue the dog, now that it has money. As the dog is merely the beneficiary of a trust, it’s not clear to me that there is a viable claim here, but it’s perhaps a natural consequence of the animals-have-standing-to-sue argument.


  • Mrs. Helmsley signed off on an Income Tax Filing that included a questionable deduction for work on her mansion. We of humble abode would have settled such a matter with payments for the taxes, interest, and penalties. Mrs. Hemsley dispute amounted to more than a million dollars, as I remember it, so she had to do time. She was discriminated against because she was rich.

    More worrisome was the public opinion that the State should imprison people for their personalities – “Rhymes with Rich.” As it happened, the more scurrilous claims against Mrs. Hemsley were from disgruntled former employees. There were other problems, too, such as compression of time. Selective listings of events that cover decades can make a normal person a devil or a saint. And reporters paid attention to those with juicy gossip.

    These biases were very prononced in the Martha Stewart case, as the reporters so obviously tried to make mountains out of molehils to paint Ms. Stewart as a witch. There was a fellow who ran a college level legal program who opined that it would be OK for the Martha Stewart jury to penalize her for being Haughty-Taughty.

    I just don’t believe the Dershowitz story. He is a real creep.

    I am pleased that this post argued that Mrs. Hemsley, as a person, deserved respect for her wishes with respect to her estate. I would go further: A Mother deserves the respect of her children with mighty few exceptions (mass murder, …)

  • Was Mrs. Helmsley really discriminated against because she was rich or simply given a greater punishment for a greater tax fraud? Compare this to simple larceny. Petty larceny in many jurisdictions has a maximum sentence of one year in jail, with jail time rarely actually given. In the same jurisdictions, grand larceny typically calls for a minimum sentence of one year in prison. So, for what is basically the same crime, offenders typically receive jail time when the amount is large, no jail time if the amount is small.

  • To be fair, Dershowitz didn’t reveal anything confidential: he recounted an incident that occurred in a public place, one having nothing to do with a legal matter.

    The story is quite consistent with other accounts of Helmsley’s poor behavior. Why is it so incredible?

  • My recall is that Helmsley’s tax bill in the year
    in question was in the neighborhood of $51M, the
    feds wanted $52M. Her jailing was of a similar
    character to Martha Stewart’s, done because they
    could when a variety of options were available.
    It is ‘justified’ because she was not a nice
    person. Hubby was let off because of senility
    though it was a joint return.

  • For Steve Hodges,

    My memory is that a $1 million dispute generates a required imprisonment. I just spent some time trying to verify my memory, but to no avail. Is my memory wrong?

    You are absolutely right. A difference in a 2% range on a complicated tax filing should be handled with fines and penalties. Putting Mrs. Hemsley in an unfavorable light sold papers and magazines. It was a shameful event in our history.

    Marc Rich also faced a disagreement over taxes, which disagreement was made a criminal matter. For that fellow, Martin Ginsberg, the tax expert’s tax expert, said that Mr. Rich was right.

  • Marc Rich was also indicted for illegally trading with Iran.

    Whether or not he was “right” about his taxes, his cowardly decision to avoid facing the charges and argue his side is enough to make me think he’s certainly no civic role model.

  • Paul,

    Both the tax charge and the trading with Iran were arcane matters. To whom would Marc rich argue? We saw what happened in the Martha Stewart case. She was only painted as a cheater. Mr Rich was painted as a traitor, too. I recommend the book “Until proven innocent” about the Duke Rape case. The boys worked hard to avoid a jury trial, and they succeeded, even though they were indited.

    By the way, Dick Cheney also traded with Iran. It was a ridiculous charge for both men.

  • As an aside, the grandchildren probably had no use for Leona and probably hated her, so it is says a lot about the kind of people they are that they felt somehow entitled to her money. Leona and Harry didn’t have any biological children of their own did they? If all the grandchildren are from Leona’s late son Jay then that would seem to make them even less entitled considering Helmsley wasn’t Jay’s father and Leona’s money is really Harry Helmsley’s. But it was still incredibly despicable how she reportedly treated the two who were disinherited.

  • Queen of Mean to people but loyal to dogs. A few million to fullfill her vague request to “help dogs” shouldn’t be out of the question. United States Humane Society is established and could put it to good use, versus humans who want money out of greed. Dogs/animals have no ego so money means nothing to them but what it can do for them, is a humane solution.

  • […] Ted and I have covered this phenomenon in the context of Leona Helmsley’s eccentric will, and now […]