Skip to main content
Leona Helmsley

Leona Helmsley

Search complete. 49 mentions across 15 episodes found for "Leona Helmsley".

Sep 14, 2026

Brian McDonaldGUEST
29:26
He had three kids in college at the time.
Brian McDonaldGUEST
29:28
Uh, his neighbor in Flushing was a man named Eddie Brady, who was a detective in the New York City Police Department, and Eddie was working hotel security for Harry and Leona Helmsley, owners of, among other things, the Helmsley Palace in New York.
Brian McDonaldGUEST
29:42
A, a ...
Brian McDonaldGUEST
29:42
Now, years before Donald Trump, uh, Harry Helmsley was the preeminent real estate mogul in New York City.
Brian McDonaldGUEST
30:14
Bill would end up working for Leona for 20 years.
Brian McDonaldGUEST
30:17
All the Feehan kids would work for her as bellhops and waitresses in the, uh, hotel, uh, restaurants, and Bill would often remind them that it was Leona who paid their college tuition.
Brian McDonaldGUEST
30:28
After 20 years of working for Leona Helmsley, she threw him a cocktail party.
Brian McDonaldGUEST
30:33
Things didn't work out as nicely for her in her later years.
Anthony ScaramucciHOST
7:07
We're not as wealthy as these guys, but sometimes when you get so wealthy, uh, it, it can cause you to start thinking about yourself differently than other people.
Anthony ScaramucciHOST
7:18
You know, what did Leona Helmsley say? You know, the, the little people, right? Y- y- you know, not us, right? Uh, Fitzgerald said the rich think differently than you and I, and I'm just wondering if that's laced in this story.
Anthony ScaramucciHOST
7:29
There's a cautionary tale in this story about wealth and almost, like, psycho- cosis and, uh, you know, so- sociopathic, uh, behavior.
Anthony ScaramucciHOST
7:41
Am I missing that, Bill, or is that-
Russell HowardHOST
28:47
Incredible.
Russell HowardHOST
28:48
Hotel magnate Leona Helmsley, who's died in New York, age 87, notoriously spoiled her bitch Trouble.
Russell HowardHOST
28:54
Leona, dubbed the Queen of Mean, uh, she's left some relatives seething after leaving them nothing.
Russell HowardHOST
28:59
Left it all to the hound.
Mark SimoneHOST
7:51
Now, apparently Hillary makes sure that it's all males working with Clinton.
Mark SimoneHOST
7:58
Remember Leona Helmsley? Remember that awful Leona Helmsley? She went to prison.
Mark SimoneHOST
8:02
And her husband, Harry Helmsley, was so sick he had to have nurses around the clock.
Mark SimoneHOST
8:07
She made sure that there were only male nurses.
Mark SimoneHOST
8:09
Now, apparently Hillary makes sure that it's all males working with Clinton.
Mark SimoneHOST
8:15
Remember Leona Helmsley? Remember that awful Leona Helmsley? She went to prison.
Mark SimoneHOST
8:20
And her husband, Harry Helmsley, was so sick he had to have nurses around the clock.
Mark SimoneHOST
8:25
She made sure that there were only male nurses.
Steven WeinstockHOST
0:09
The building was the Empire State Building.
Steven WeinstockHOST
0:11
The man was Harry Helmsley.
Steven WeinstockHOST
0:14
And by the time he was done, he controlled 27 hotels, more than 50,000 apartments, and some of the most recognizable skylines in New York, all built on a financing trick.
Steven WeinstockHOST
0:26
that he helped invent.
Steven WeinstockHOST
0:33
This is another one of our deep dive episodes here on The Wealth Clock.
Steven WeinstockHOST
0:37
Here's how a kid from the Bronx with no college degree became one of the largest private real estate owners in American history and how the second half of his life ended up defined less by what he built than by the woman he ended up marrying.
Steven WeinstockHOST
0:52
Harry Brackman Helmsley was born in Manhattan, in 1909 and grew up in the Bronx, the son of Henry Helmsley, a wholesale dry goods buyer, named Minnie Brackman.
Steven WeinstockHOST
1:05
The family didn't have any money for college, and Harry didn't even finish high school, dropping out of Evander Childs High School before graduating.
Ken StrodeHOST
32:18
The picture he sent in.
Doug VaughnHOST
32:20
But you did find Leona Helmsley attractive.
Ken StrodeHOST
32:22
Beer Cats and Hot Wife Autumn.
Ken StrodeHOST
32:23
I don't even remember what she looked like.
Ken StrodeHOST
32:25
That's why I stand corrected.
Tim McKernanHOST
32:25
Is there a picture of Iggy changing Leona Helmsley's pull-ups?
Ken StrodeHOST
32:28
That wouldn't be pretty.
Doug VaughnHOST
32:30
[laughs]
Jackson BurkettHOST
36:12
...
Jackson BurkettHOST
36:12
I mean, Iggy was with Leona Helmsley.
speaker_0AUDIENCE
36:15
She told me that she's on a pension from McDonnell Douglas, if that tells you anything.
Jackson BurkettHOST
36:19
Oh, God, yeah.
Jackson BurkettHOST
38:29
[laughs]
Doug VaughnHOST
38:30
I like sausage as much as the next guy.
Jackson BurkettHOST
38:32
Would this be a pre-depression cuck like Iggy with Leona Helmsley? That's from Big Walt's Missing Teeth.
Doug VaughnHOST
38:37
Pre-depression.
Bruce CarlsonHOST
79:38
The Don would win the headline.
Bruce CarlsonHOST
79:39
When he ran up against his rival, Leona Helmsley, real estate rival, he used the press to savage her.
Bruce CarlsonHOST
79:46
Found out that former employees have said that she was vicious.
Bruce CarlsonHOST
79:49
You don't treat people that way, Trump would say in the newspaper.

5 more episodes mention Leona Helmsley.

Create an account to see the whole feed, search across every transcript, and follow the entities you care about.

We value your privacy

We use cookies to understand how you use our platform and to improve your experience. Click “Accept All” to consent, or “Decline non-essential” to opt out of non-essential cookies. Read our Privacy Policy.