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Last Updated: Thursday, October 1, 2026 at 07:43 PM
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Leona Helmsley shows her love for Trouble

Olbermann: The woman who famously said "only the little people pay taxes," decided that a little dog gets the largest single bequest from her inheritance. Just to recap, Leona Helmsley died last week leaving a $ 4 billion fortune made by investing in luxury hotels, cheating on taxes and abusing employees.

The woman who famously said "only the little people pay taxes," decided that a little dog gets the largest single bequest from her inheritance. Just to recap, Leona Helmsley died last week leaving a $4 billion fortune made by investing in luxury hotels, cheating on taxes and abusing employees.
      
She served two years for tax fraud, once sued her only son's estate after he died because he owed her money and earned a reputation, as one writer put it, as the Lady McBeth of the lodging industry.  And now from beyond the grave, one more "up yours" from Leona.

Her favorite Maltese lap-dog, Trouble, has been named as the largest individual beneficiary in her will, inheriting $12 million.  Trouble will also be laid to rest, when the time comes, right next to Helmsley in an ornate, million dollar, stained glass and granite mausoleum which is to be steam cleaned at least once a year, in perpetuity.  

Leona always prided herself on the housekeeping at her hotels.  As for her only four grandkids, she cut two of them out of her will entirely for, as the will states, "reasons which are known to them." So far they're not telling. Two other grandchildren get $5 million each but only if they visit their father's grave at least once a year and sign in to prove it.