Trump Nemesis and Queen of Mean Leona Helmsley Subject of Juicy New Documentary (EXCLUSIVE)

A juicy new documentary about the life and public battles of late real estate mogul Leona Helmsley is currently in production, Variety has learned exclusively.  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 Giuliani in 1988.

Helmsley was an icon of the “greed is good” era, an owner of luxury hotels and condominiums who left behind a $5 billion estate (which famously included a $12 million trust fund for her dog, a Maltese). Branded the “Queen of Mean” by the New York tabloids for her acid tongue and regal air, she was a bitter rival of Trump — who once called her “a disgrace to the industry and a disgrace to humanity in general.” Of Trump, Helmsley once reportedly said: “I wouldn’t trust him if his tongue was notarized.”

Trump notoriously tried to snatch the crown jewel of Helmsley’s property portfolio, the Empire State building.

Indie studio Gunpowder & Sky has boarded the project from Filmbank’s Keith Robert Patterson (HBO’s “All About Ann”), who will direct and produce. Former head of development at Wavelength, Serena Turner, and Emil Pinnock are also producers. The trio has additionally optioned Mitchell Pacelle’s book “Empire: A Tale of Obsession, Betrayal and the Battle for an American Icon,” for a scripted adaptation that Patterson is also writing and producing. Joanna Zwickel, senior vice president of documentary features and series, is overseeing for Gunpowder & Sky.

The project will explore Helmsley’s journey from the “belle of New York society to pariah overnight,” filmmakers said, after she was indicted for tax evasion. The case was sparked after allegations she and husband Harry allegedly used millions from their business to renovate their Greenwich, Connecticut, mansion.

“From day one, Leona Helmsley alleged that she and husband Harry were framed and that her prosecution was thrown. It’s taken 30 years to uncover the exclusive tapes, evidence, and participation from those willing to come to her defense,” said director Patterson. “And now, through recently unearthed exclusive audio and interviews, Leona will finally be able to mount a real defense.”

Zwickel said Helmsley was “one of the first public figures to ever be canceled — she and her husband Harry were New York royalty and literally overnight she became known as the ‘Queen of Mean’. We are thrilled to be partnered with Filmbank, Keith Robert Patterson and Serena Turner on this film that will finally reveal if Leona was mean, a misunderstood genius, falsely maligned by Donald and the legal system — or all of the above. This doc will expose it all.”

Filmbank, an Unconditional Content company, is currently in development on a television series based on the hit haunted house video game “The 7th Guest.” The scripted Helmsley project will also be produced by Pinnock and Entertainment 360’s Jenna Sarkin.

Gunpowder & Sky targets larger-than-life stories about groundbreaking music and musicians, pop culture, issues and personalities. Most recently, they produced the acclaimed Sheryl Crow documentary “Sheryl,” premiered on Showtime and screened at SXSW. The company has two new music documentaries that chronicle the worlds of soft rock and 80s hair metal that will debut later this year on Paramount+.  Other recent projects include “Last Exit: Space,”  written and directed by Rudolph Herzog and executive produced and narrated by Werner Herzog for discovery+

Read on for a Q&A with Patterson:

What about Leona’s story feels relevant?

Recently, everyone has been questioning the legal justice system. We have very good evidence that Leona was railroaded, and if it can happen to a billionaire, it can happen to anyone. She alleged that her case was rushed by then SDNY Prosecutor Rudy Giuliani for nefarious reasons.

How do documentary subjects and those close to Helmsley or the time period shed light on her?

I think the recent turmoil and polarization in the media is shedding light on stories that need to be reexamined with the benefit of time. Leona had few friends as most left her high and dry when she was “cancelled” by the New York press. We have her few friends involved with our project and what they know is revelatory.

Did you have any preconceived notions about Leona that were reversed after making the film?

We received a tip from an insider about the Leona prosecution. Then I discovered the “Leona is a bitch” narrative was started by none other than Donald Trump, when he was competing against her and Harry. That immediately intrigued me. When we started chipping away at that 1989 narrative we were shocked —  I mean, jaw on the floor — with what we uncovered. We have unprecedented access to those close to what happened and who want to set the record straight to be on the right side of history. We can’t give that much away, but you will be shocked. I promise. This is “The Jinx”-level stuff.

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