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  1. Jul 14, 2021 · As two larger-than-life real-estate personalities, Leona Helmsley and Donald Trump loathed each other. Trump called her “a disgrace to the industry and a disgrace to humanity in...

    • Caroline Howe
  2. Jul 17, 2021 · And when Helmsleys tax fraud trial began, Trump gloated: “I can feel sorry for my worst enemy, but I cannot feel sorry for Leona Helmsley. She deserves whatever she gets.”

  3. Jul 2, 2021 · Multiple reports and social media posts referenced Trumps 1989 comments about fellow New York real estate developer Leona Helmsley, who was later convicted of evading $1.2 million in...

    • Aaron Blake
  4. May 25, 2022 · The film will contain never-before-heard tapes of Helmsley and her archrival Donald Trump, as well as “smoking gun” evidence that will question the tax evasion case brought on her by Rudy ...

    • Matt Donnelly
  5. Jul 2, 2021 · On July 1, MSNBC's Rachel Maddow compared former President Donald Trump to his former rival, real estate magnate Leona Helmsley. Back in 1989, Helmsley and her husband, Harry, were convicted of tax fraud after it was discovered that the couple, who owned a hotel and real estate empire in New York, had been billing their businesses for millions ...

    • Ashley Moor
  6. May 23, 2016 · In the nineties, Trump, in a bid to control the Empire State Building, said that the Helmsleys’ management had turned it into a “high-rise slum”; they sued him for a hundred million dollars.

  7. Jul 2, 2021 · And Donald Trump himself kicked Helmsley when she was down, leaking a letter to the New York Post in 1988 amid an easement dispute over an Atlantic City property Trump bought from Penthouse...

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