Leona Helmsley (Documentary)

Leona Helmsley was once the most powerful woman in New York, with a hotel empire spanning the entirety of the United States. In her climb from the working class to high society, she made a few enemies along the way - namely because of her aggressive management style.

Additional sources:

[philipdraper]

I’ve been reading “Queen of Mean” and am floored that this woman was given so much power by her husband in running their business. I deduce from the book that there were so many missteps in the financial management of the Helmsley Organization under her direct control. It boggles the mind but sometimes chutzpah and intimidation work better than actual knowledge and experience. She was tyrannical but extremely gifted with an iron will to control and irrationally alienate others into doing what she wanted, no matter how ridiculous.

[guydreamr]

Her negative attributes were no caricature. Her peccadillos have been extensively documented in numerous books like "Queen of Mean, " "Palace Coup, " "The Rise and Fall of Harry and Leona Helmsley, " and others. The woman was vile.

[Nunya_Bidness_]

The sad part is when they introduced the income tax they said:
"Oh don't worry, only the Rich will have to pay.'
Then it was:
"Well the middle class will have to pay too--but not the poor!"
Next,
"We lied, the poor have to pay too!"
Then finally:
"The Rich don't have to pay a damn thing, fuck

[owensmith]

I thought rich people leaving their wealth to a pet was a meme...

[joanne]

Very interesting documentary. I remember the news stories about her in the 80's and 90's. Still shocked at her behaviour. I liked the sketch of the jury during her trial. Possibly some of those tax paying "little people"? Great job done on this Joseph!

[ohigetjokes]

Love how you keep digging up these stories - and cool Magnum PI cameo lol

[ryancalic]

She never learned the meaning of the biblical proverb: "It is easier for
the camel to pass through the eye of the needle than it is for a rich
man to enter heaven."

[andyroo]

I was in high school when this story broke. My mother was following the story and would talk about it. I have no hesitation in thinking this woman was a cut throat. She went after what she wanted and left destruction behind her. I wonder if she really ever loved Harry Helmsley.

[EvangelistRBColbert]

She was telling the truth! It doesn't pay to be poor in America. Earned income will always be taxed more than entrepreneur's salaries and capital gains from investments.😊

[MsNooneinparticular]

That's the meanest looking human I've ever seen. The evil just oozed out of her like some kind of Disney villain. A year out of a 16 year sentence... how'd they justify *that*? Glad her kids got some of the money left to the dog. They deserved it for having her as a mom, and I know it would've eaten her up.

[johnsax]

Poor Leona, so greedy, so ungrateful for her good fortune.

[MediaSubliminal]

..."hired private investigators..."
shows a picture of Magnum PI

[mzcytin]

"We don't pay taxes. Only the little people pay taxes" 🤷‍♀️ but did she lie?

[BluetheRaccoon]

That someone could come from such humble beginnings and have such a sense of entitlement and complete lack of empathy is proof of narcissism. She never deserved any of it, and it would have been grand to see her humiliated fiercely. She grew up during the great depression, ffs.

[Mimikinn]

Just goes to show that no amount of money can buy you class.

[trevnti]

I think your stories are so interesting and unique the YT algorithm doesn't pick it up. IT SHOULD AND NEEDS TO!!!

[Hillers]

At 2:12 ...you can really see the "love" in her eyes...

[SaurianSavior]

In April 1989, Donald Trump attacked Leona for her habit of firing employees that crossed her. This is the darkest timeline.

[LBF]

Did Leona Helmsley really make that quote that only the little people pay taxes or was that like "Let them eat cake".

[dennisbarrett]

I bet 101 dalmatians were celebrating at a cookout, when they heard she passed away. And partying like it's 1999.