If Donald Trump were a woman, Hillary Clinton would be facing off against Leona Helmsley

I’ve always wanted to be the biggest real estate man to come down the pike.


The American election—it’s getting too much. There are so many levels of serious dysfunction; immoderate dosing is bound to have a lasting effect, like reading too much about serial killers. It could have a long lasting effect on the way you look at the world.

But the barn door has closed. MSNBC presenters feel like extended family. American journalists rattle around in my Twitter feed panting about Dr. Oz and ranting about the state of political reporting in what’s becoming close to equal measure. And just as I’m about to nod off to sleep, I bring one more Washington Post story up on my phone.

Oh well.

Gender is one obvious theme.

In the laboratory of a U.S. presidential election cycle, it’s is clearly a big variable in 2016. Hillary Clinton being the first woman ever nominated for president by a major political party in the U.S allows us the chance to study it under a microscope.

Political professionals have always known that running a woman candidate is different than running a man. As I learned from many political strategists—some of who are on TV now so must be smart—you start from a different premise when you run a woman.

Cathy Allen, one of the U.S. political strategists I learned a lot from, is an expert on running women candidates. Here are some traditional rules from Cathy and her colleagues for women running for office.

  1. Focus on qualifications. You’ll need to be twice as capable to be given half the consideration.
  1. Follow certain rules of appearance. Dress conservatively, preferably in a suit, with a bobbed or shorter haircut. Be shown in a formal setting. Informal settings on a golf course in shorts, for example, or powering a motorboat in a swimsuit won’t help.
  1. Support the death penalty. Voters think women might be “too compassionate.” You can’t just talk about being tougher you have to be tougher. The war on terrorism is a tricky spot for women candidates and can be a trap door if you’re seen as too soft.
  1. Watch your voice. Lower, louder, slower. Shrill voice – bitchiness
  1. Hide your husband. The political spouse advantage doesn’t work for women. If hubbie is on the campaign stage with you, people tend to think he’s really running to show. And, as a bonus, his scandals will be your scandals.
  1. Don’t be too passionate. Woman can be seen to go “overboard” on their issues.
  1. Don’t cry. It’s good for a man, not for a woman. See #2.
  1. Don’t do anything that could be perceived as a breach of integrity. As Cathy Allen writes, “if a woman is caught lying, whether it’s on her resume, her voting record, her campaign contribution reporting, or conflicting comments to different special interest groups, she’s in trouble bigtime. Because the voters see woman as more honest, when she abuses that trust, she seldom can regain the voters’ trust. They hold women more accountable than men, and though that may seem unfair, it’s very true.”

We know that women candidates have to run different campaigns than their male counterparts, but what if we could, in the interest of science, reduce the gender variable in this election cycle and have Hillary Clinton running against other woman.

It couldn’t be just any woman, of course, because Trump is not a normal man. It would have to be a Trumpian woman.

Who would that woman be?

rhymes-with-richIn a daydream, I settled on Leona Helmsley. She was the New York City developer who, with her husband, Harry Helmsley, owned acquired condo properties and 23 luxury hotels during the 1980s and 1990s.

She was known for her flamboyance, approach to taxation (“We don’t pay taxes. Only the little people pay taxes”), verbal manhandling of employees and poor treatment of sub-contractors (often refusing after work had been done on her properties).

Called “The Queen of Mean,” she was charged and convicted of tax evasion in 1994 (prosecuted by one Rudy Giuliani), served 19 months in prison, and died of congestive heart failure at the age of 87 in 2007. The contents of her will made front-page news when she left $12 million to her dog, Trouble.

She and Donald Trump were, during the 1980s and 1990s, the most well known New York City real estate magnets. They were both  constantly on the cover of the tabloids for their ostentatious billionaire lifestyles and outrageous commentary.

And not to put too fine a point on it, Trump hated Leona Helmsley. In April, 1989, The Washington Post reported that:

“Donald J. Trump has shaken the onyx and marble foundations of the hotel world by calling his equally overpublicized rival, Leona Helmsley, a “disgrace to humanity.” In a deliciously vitriolic letter to the self-proclaimed Queen of the Helmsley hotel empire, The Donald (as he is called by his relentlessly glamorous wife Ivana) displays a previously hidden capacity for venom by slicing The Leona into tiny little pieces. “Without the veil of Harry Helmsley, you would be a non-entity. You would not be able to randomly fire and abuse people in order to make yourself happy…”

“One friend of Trump’s called the letter a reflection of “a very deep hatred” that has been simmering how-donald-trump-explains-america-806-body-image-1438884501for 15 years.”

According to Crains New York, among their rivalries was the fate of Empire State building, to which Harry Helmsely and a partner bought in 1961 for $65 million. In 1991, Trump “purchased” it with a Japanese consortium and the Helmsley’s managed it. (“Purchased” it is a bit of a stretch for Trump. The consortium provided the money and Trump provided his name. But written into the agreement was Helmsley continuing to manage the property.)

In 1995, Trump sued the Empire State Building leaseholders, arguing that they had let the tower go to seed and thus had violated their lease. A few months later, an appellate court ruled in favour of the Helmsleys and Trump’s takeover bid was over. In the meantime, his Japanese partner was imprisoned for a fire in a hotel he owned.

Trump’s Empire State Building dreams were over, but their rivalry continued.

Rivals can be so much alike in some ways.

Leona owned the phrase, “you’re fired” before Donald Trump ever uttered the word on reality TV.

In a Playboy interview, Helmsley said, “I wouldn’t trust Donald Trump if his tongue was notarized.”

If only she were alive to play Donald J. Trump in Hillary Clinton’s debate prep.

All in the interest of reducing variables, of course. As overexposed observers we could, at least, take gender out of the mix.



Gail PiAuthor Photo 01 Sandy Tam Photographycco is a strategist who has worked in the nonprofit sector for 25 years, most of which as President of Gail Picco Associates. Prior to establishing Gail Picco Associates, she spent eight years working in a shelter for assaulted women and children. She is the author of What the Enemy Thinks, a recent novel set in the nonprofit sector, of Your Working Girl, a blog of memoir and commentary on politics, charity and popular culture, and writes a regular column for Hilborn Charity News. She is a Principal with The Osborne Group in Toronto and Chair of the Regent Park Film Festival. 

Enter your email address to follow this blog and receive notifications of new posts by email.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: