Donald Trump’s Gross History of Misogyny: From Rosie O’Donnell to Megyn Kelly

The GOP presidential frontrunner has come under fire for a series of sexist comments he’s made towards Fox News host Megyn Kelly. But Trump’s women-bashing goes back decades.

08.08.15 8:21 AM ET

If you’ve ever fancied seeing a dais of ten adult men who looked as if they’d been clothed by their mothers cower under the pressure of a confident, brash, and brilliant woman brimming with agency, then Thursday night’s opening round of televised GOP presidential debates was for you.

An astounding 24 million viewers tuned in to the two-hour carnival of chest-thumping and let’s make America great again nebulosities, presided over by a talking turtle, the spawn of Tan Mom, and Fox News superstar Megyn Kelly, who proved to be the Ronda Rousey of questioning, hammering the White House hopefuls on their most glaring weaknesses.

And Kelly reserved her biggest swing for Donald Trump, the bombastic, elaborately coiffed real estate mogul currently topping the polls:

“You’ve called women you don’t like fat pigs, dogs, slobs, and disgusting animals. Your Twitter account has several—”

Trump then interrupted Kelly, raised his finger in the air like a bloated, illegal immigrant-hating E.T., and with a smirk replied, “Only Rosie O’Donnell.”

Kelly soldiered on: “Your Twitter account has several disparaging comments about women’s looks. You once told a contestant on Celebrity Apprentice it would be a pretty picture to see her on her knees. Does that sound to you like the temperament of a man we should elect as president, and how will you answer the charge from Hillary Clinton, who is likely to be the Democratic nominee, that you are part of the war on women?”

The Donald—as is his wont—deflected the question, launching into his usual spiel about China before patting himself on the back for his lack of political correctness.

Instead, he saved his petty griping for the early morning hours following the debate, unleashing a Twitter tantrum aimed at Republican pollster Frank Luntz and Kelly, sharing a tweet referring to the striking pundit as a “bimbo”:

Trump doubled down on the comments Friday night in an interview with CNN’s Don Lemon, implying that Kelly was on her period during the debate. “You could see there was blood coming out of her eyes, blood coming out of her… wherever…” he said.

It was a disgustingly sexist statement, and one that drew the ire of many Republicans—including Republican presidential candidate Carly Fiorina and Red State’s Erick Erickson, who rescinded his invitation for Trump to speak at a conservative gathering Saturday night.

But these chauvinistic comments directed at Kelly are just the tip of the iceberg when it comes to Trump’s rampant misogyny and cruelty towards women.

Trump married the stunning Czech model Ivana Zelníčková in 1977, and the couple had three children. According to People magazine, by the late ‘80s, he began cheating on his spouse with Marla Maples, a bit actress and ex-Miss Hawaiian Tropic. “By 1987, during services at the Marble Collegiate Church in Manhattan, Trump was secretly romancing Maples as he found ways to temporarily ditch Ivana and their kids, Donny, now 19, Ivanka, 15, and Eric, 13,” wrote People.

The affair persisted until Donald and Ivana’s infamous 1989 Christmas holiday in Aspen.

“I saw him walking with his arm around a blond and I just assumed it was Ivana,” a Chicago decorator who spent the holidays in Colorado told the Chicago Tribune. “Same size, same hair. I walked around to look, but it wasn’t her.”

It was reportedly Marla Maples, Trump’s mistress. And shortly thereafter, Trump and his wife engaged in a lengthy argument on the slopes.

Trump and Ivana’s split was messy, to say the least. “First he briefly locked his wife, whom he used to refer to as ‘my twin as a woman’ out of her office at his Plaza Hotel, then he compared her to Leona Helmsley, a woman he called `a truly evil human being.’ Maybe it`s a good thing they both hired—not divorce attorneys—but criminal attorneys to fight for their right to unparty,” wrote the Tribune.

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Around that time, Trump sat down for an interview with Esquire, where he infamously remarked, “You know, it doesn’t really matter what [the media] write as long as you’ve got a young and beautiful piece of [expletive],” he told Esquire in 1991.

During the heated divorce proceeding, Ivana accused Trump of “rape,” as revealed in the 1993 book Lost Tycoon: The Many Lives of Donald J. Trump.

According to Harry Hurt III’s book, Trump confronted his then-wife after undergoing an agonizing scalp reduction surgery to remove a bald spot. He’d used the plastic surgeon based on Ivana’s recommendation, and was none too happy about it.

“Your fucking doctor has ruined me!” Trump cried. He then, according to Lost Tycoon, proceeded to engage in a “violent assault” against Ivana, holding back her arms, pulling out fistfuls of hair from her scalp, tearing off her clothes, and unzipping his pants.

“Then he jams his penis inside her for the first time in more than sixteen months. Ivana is terrified… It is a violent assault,” Hurt writes. “According to versions she repeats to some of her closest confidantes, ‘he raped me.’”

Trump’s vehemently denied that the incident took place, and Ivana, who was awarded a hefty sum in the divorce, has since recanted her testimony on numerous occasions.

In 2001, during an on-air spat with gossip columnist (and Trump acquaintance) A.J. Benza, the snooty businessman bragged for half an hour about stealing the gossip columnist’s former girlfriend, model Kara Young. “A.J., any girl you have, I can take from you if I want,” Trump said during the kerfuffle. “You’re full of shit. So any girl you have, I can take. That I guarantee. That was proven before.”

The Donald’s way with words when it comes to women was on full display in his 2004 tome Trump: How to Get Rich, where the then-host of the NBC reality competition series The Apprentice shared a number of sexist remarks about his show.

“All of the women on The Apprentice flirted with me—consciously or unconsciously. That’s to be expected,” he bragged. “The early victories by women on The Apprentice were to a very large extent dependent on their sex appeal,” wrote Trump, later adding, “I believe we’re all equal except women still have to try harder and they know it. They will do what they have to do to get the job done and will not necessarily be demure about it.”

Not to be outdone, in his 2006 book Trump 101: The Way to Success, he compared women to inanimate objects. “Beauty and elegance, whether in a women, a building, or a work of art is not just superficial or something pretty to see,” wrote Trump.

But the real estate tycoon’s silly, bloviating books pale in comparison to his verbal assault on actress and TV host Rosie O’Donnell.

After O’Donnell took Trump to task in 2006 for defending Miss USA Tara Conner, Trump began publicly referring to O’Donnell as a “fat pig” and “animal.” He also spewed an outrageous two-minute rant against O’Donnell to Entertainment Tonight:

“Rosie O’Donnell is disgusting—both inside and out. If you take a look at her, she’s a slob. How does she even get on television?... If I were running The View, I’d fire Rosie. I’d look her right in that fat, ugly face of hers and say, ‘Rosie, you’re fired.’ We’re all a little chubby but Rosie’s just worse than most of us. But it’s not the chubbiness—Rosie is a very unattractive person, both inside and out. Rosie’s a person that’s very lucky to have her girlfriend and better be careful or I’ll send one of my friends over to pick up her girlfriend. Why would she stay with Rosie if she had another choice?”

In a scene eerily reminiscent of his O’Donnell-bashing, in 2011, New York Times writer Gail Collins detailed an unfortunate episode with Trump in a Times op-ed, writing, “During one down period, I referred to him in print as a ‘financially embattled thousandaire’ and he sent me a copy of the column with my picture circled and ‘The Face of a Dog!’ written over it.”

Not even his own daughter was immune to his gaze. During a 2006 interview on The View, Trump notoriously remarked, “I don’t think Ivanka would do [Playboy], although she does have a very nice figure. I’ve said if Ivanka weren’t my daughter, perhaps I’d be dating her.”

Then, he appeared on CNN’s Larry King Live and took it upon himself to give his two cents on Angelina Jolie’s fractured relationship with her father, the actor Jon Voight. “I think he’s a great actor and she just treats him terribly,” said Trump. “She’s been with so many guys she makes me look like a baby, OK, with the other side. And, I just don’t even find her attractive. That has nothing to do with why I said it though.” Jolie’s mother, Marcheline Bertrand, divorced Voight in 1978 after he cheated on her.

The following year, in 2007, Trump began developing a show with Fox called Lady or a Tramp. According to Variety, Tramp was “a reality-competition series in which girls in love with the party life will be sent to a charm school where they will receive a stern course on debutante manners.” What’s more, “Girls are required to wear tweed skirts and pearl necklaces, and taught the finer points of skills like flower arranging and needlework.” Variety claimed that Trump would serve as executive producer and “possibly come on air to evaluate contestants’ progress,” though the series thankfully never saw the light of day.

Trump’s opinions on celebrity relationships weren’t confined to Rosie O’Donnell and Angelina Jolie. In 2008, Trump insinuated that very successful actress Anne Hathaway was a gold digger after she split from hubby—and Trump Tower resident—Raffaelo Follieri right before he was indicted for fraud. “She hasn’t remained very loyal to him, has she?” Trump told Access Hollywood’s Billy Bush. “So when he had plenty of money, she liked him, but then after that, not as good, right?” He also ripped Huffington Post founder Arianna Huffington, tweeting, “[Arianna Huffington] is unattractive both inside and out. I fully understand why her former husband left her for a man—he made a good decision.” That same year—2012—Trump became temporarily obsessed with Kristen Stewart’s breakup from her Twilight co-star Robert Pattinson, tweeting, “Robert Pattinson should not take back Kristen Stewart. She cheated on him like a dog & will do it again—just watch. He can do much better!”

If that weren’t enough, during a 2013 interview with Howard Stern, Trump critiqued the looks of several A-list women, including Halle Berry (“I love her… upper body”), Kim Kardashian (“Does she have a good body? No. Does she have a fat ass? Absolutely.), Jessica Chastain (“she’s certainly not hot”), and more.

In 2009, Miss USA contestant Carrie Prejean released a memoir entitled, Still Standing: The Untold Story of My Fight Against Gossip, Hate, and Political Attacks. Prejean wrote about what is allegedly known as “The Trump Rule”—that Miss USA pageant contestants are forced to flaunt their wares in front of pageant owner Trump so that he could play his own personal game of Hot or Not. 

“Many of the girls found this exercise humiliating,” Prejean wrote. “Some of the girls were sobbing backstage after [Trump] left, devastated to have failed even before the competition really began . . . even those of us who were among the chosen couldn’t feel very good about it—it was as though we had been stripped bare.”

And lest we forget the incident in 2012 when Trump called in to TMZ and threatened to show defense attorney Gloria Allred his penis. “I think Gloria would be very very impressed with [my penis],” bragged Trump

Back to The Apprentice. In 2010, two of the reality series’ former contestants complained to the New York Post about creator/host Trump’s “sexist” behavior.

“So much of the boardroom discussion concerned the appearance of the female contestants—discussing the female contestants’ looks—who he found to be hot,” Apprentice hopeful Mahsa Saeidi-Azcuy told the Post. “He asked the men to rate the women—he went down the line and asked the guys, ‘Who’s the most beautiful on the women’s team?’”

“I think it was most uncomfortable when he had one [female] contestant come around the board table and twirl around,” contestant Gene Folkes added.

Then there was the statement invoked by Kelly in the debate wherein Trump, on a 2013 episode of NBC’s Celebrity Apprentice, was busy grilling contestants Bret Michaels and Brande Roderick. Michaels described how Roderick had gotten down on her knees and begged the rocker not to be fired. “Excuse me, you dropped to your knees?” an amused Trump asked Roderick. “Yes,” she replied. Cue Trump: “It must be a pretty picture—you dropping to your knees.”

Last month, The New York Times reported that Trump had a meltdown during a deposition when a lawyer requested a brief break from the proceedings to pump breast milk.

“When the lawyer, Elizabeth Beck, asked for a medical break, Mr. Trump and his lawyers objected, demanding that the deposition continue. Ms. Beck said it was urgent—she needed to pump breast milk for her 3-month-old daughter, and she took the pump out to make a point,” wrote the Times. “Mr. Trump erupted. ‘You’re disgusting,’ he told Ms. Beck, in a remark that is not disputed by either side. He then walked out of the room, ending the testimony for the day.”

Now, Trump is receiving backlash from his own party for his series of misogynistic comments directed at Fox News’ Kelly. Strangely enough, writer Anna Holmes predicted that Trump’s antiquated attitudes towards women would be his downfall in a Washington Post op-ed from 2011.

“Perhaps this legacy of unapologetically gleeful misogyny—not his reputedly shady business practices or his absurd questions about President Obama’s birthplace—will end up being Trump’s electoral Achilles’ heel,” wrote Holmes. “Despite his protestations over the years that he ‘loves’ and ‘respects’ women, the fact of the matter is that whatever their party identification or their positions on the economy, foreign policy or abortion rights, women don’t take kindly to being defined by their body mass index, their mothering skills or their supposed disposability.”