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Story highlights

Clinton criticized Trump for his words about women during Monday's debate

He has a long history

(CNN) —  

As Hillary Clinton on Monday night reeled off a litany of insults he had leveled against women through the years, including some nasty nicknames for a former Miss Universe, Donald Trump leaned into his microphone and asked repeatedly, “Where did you find this? Where did you find this?”

The Clinton campaign need not have looked far, or particularly hard, to turn up instances of the Republican presidential nominee speaking in cold or cruel ways about women. Trump has made a habit of it over the years, targeting public figures, even his own wives and girlfriends.

On Tuesday, Trump even added to the list, calling into Fox News and explaining why he’d alternately described former Miss Universe Alicia Machado as “Miss Piggy” and “Miss Housekeeping.”

“She was the winner (of the pageant), and, you know, she gained a massive amount of weight, and it was a real problem,” Trump said. “We had a real problem.”

The Trump campaign has pushed back against suggestions his past comments betrayed any lack of respect for women.

“Mr. Trump has tremendous relationships with women,” spokeswoman Hope Hicks told CNN in an email, noting the presence of high-ranking female officials within his campaign and company. “To say otherwise is wholly inaccurate and based on unsubstantiated claims from publicity hungry individuals.”

But many of Trump’s nastiest affronts are matters of public record. And voters have noticed – even as he gained in recent polls, Clinton’s lead among women remained considerable, usually up around 20 points.

Here is an incomplete list of his insults over the years:

Critical women

During the first Republican primary event in August 2015, Fox News’ Megyn Kelly challenged him over his past comments about women. Trump didn’t like it.

“You could see there was blood coming out of her eyes,” he told CNN’s Don Lemon after the fact. “Blood coming out of her … wherever.”

His feud with Kelly would stretch on. Before it was informally settled, he would retweet another Twitter user who posted images form Kelly’s GQ Magazine photo shoot and called her a “bimbo.”

Trump and Rosie O’Donnell have sparred for years – right through Monday night. During her time on ABC’s “The View,” O’Donnell had disparaged Trump as a “snake-oil salesman” and discussed his bankruptcy. Trump has been especially harsh in return.

In this clip from a 2006 Entertainment Tonight segment, he called O’Donnell a “slob.”

“If I were running ‘The View,’ I’d fire Rosie. I’d look her right in that fat ugly face of hers, I’d say, ‘Rosie, you’re fired,’ ” he said, channeling his reality TV tagline. “We’re all a little chubby, Rosie is just a little worse than most of us. But it’s not just the chubbiness. Rosie is a very unattractive person, both inside and out.”

In August 2012, he mocked Arianna Huffington, whose ex-husband Michael revealed he was gay a year after their marriage ended in 1997, tweeting that she was “unattractive both inside and out. I fully understand why her former husband left her for a man- he made a good decision.”

Better Midler, too, has come under fire from Trump. In the space of six minutes on October 28, 2012, he tweeted at the singer and actress twice, first calling her “grotesque,” then adding: “While @BetteMidler is an extremely unattractive woman, I refuse to say that because I always insist on being politically correct.”

A year earlier, New York Times columnist Gail Collins wrote about a note she had received from Trump.

“During one down period, I referred to him in print as a ‘financially embattled thousandaire,’” Collins recalled, “and he sent me a copy of the column with my picture circled and ‘The Face of a Dog!’ written over it.”

On their mental health

More recently, he responded angrily to another Times columnist, Maureen Dowd, who suggested during an interview on CNN that Trump “thought the violence (at his rallies) added a frisson of excitement.”

First, Trump tweeted that Dowd was “wacky” and a “neurotic dope.” In a second post, he called her “Crazy Maureen Dowd.”

Earlier in the summer, he had used similar terms to smear now-former Democratic National Committee Chairwoman Debbie Wasserman Schultz and MSNBC host Mika Brzezinski.

Wasserman Schultz was “highly neurotic,” while he described Brzezinski, who had been critical on her show, as “off the wall, a neurotic and not very bright mess!”

And don’t forget Supreme Court Justice Ruth Bader Ginsburg. During a brief back-and-forth for which she eventually apologized, Trump tweeted: “Her mind is shot - resign!

Crude gender stereotypes

In a clip turned up by HBO’s John Oliver, Trump discusses with a female reporter how contestants at his beauty pageant are judged. Then comments on her own appearance (at 4:56).

There is a pattern. The future GOP nominee offered this assessment in his 1997 book, “Trump: The Art of the Comeback”:

“Women have one of the great acts of all time,” he wrote. “The smart ones act very feminine and needy, but inside they are real killers. The person who came up with the expression ‘the weaker sex’ was either very naive or had to be kidding. I have seen women manipulate men with just a twitch of their eye – or perhaps another body part.”

When discussing whether he might want more children with his third wife during a 2005 visit to radio host Howard Stern, Trump explained his paternal role as such: “I mean, I won’t do anything to take care of them. I’ll supply funds and she’ll take care of the kids. It’s not like I’m gonna be walking the kids down Central Park.”

More recently, as he again considered a run for office, Trump tweeted that the presence of women, simply by their presence in the ranks, were to blame for sexual assault in the military.

“26,000 unreported sexual assaults in the military-only 238 convictions,” he tweeted in May 2013. “What did these geniuses expect when they put men & women together?”

Public, sex-specific insults

Before he turned on Maureen Dowd, Trump last summer told the columnist that, “sadly,” the supermodel Heidi Klum is “no longer a 10.”

A few months earlier, the not-yet-candidate retweeted a fan who posted a question: “If Hillary Clinton can’t satisfy her husband what makes her think she can satisfy America?”

Trump deleted his own post, blaming it on a rogue staffer.

By the fall of 2015, Trump was a leading candidate for the Republican nomination. During an interview with Rolling Stone he commented on his primary rival, Carly Fiorina.

This was the scene, as reporter Paul Solotaroff described it in his story: “When the anchor throws to Carly Fiorina for her reaction to Trump’s momentum, Trump’s expression sours in schoolboy disgust as the camera bores in on Fiorina. ‘Look at that face!’ he cries. ‘Would anyone vote for that? Can you imagine that, the face of our next president?!’

What he said to the face of “Celebrity Apprentice” contestant and former Playboy playmate, Brande Roderick, during a 2013 show left her blank-faced.

“It must be a pretty picture,” Trump said. “You dropping to your knees.”

Disgust at normal bodily functions

At a campaign event in December 2015, he remarked on Clinton’s slightly delayed return from a bathroom break during a recent Democratic primary debate.

“I know where she went, it’s disgusting, I don’t want to talk about it,” Trump said. “No, it’s too disgusting. Don’t say it, it’s disgusting, let’s not talk, we want to be very, very straight up.”

It wasn’t the first time Trump had expressed some revulsion at something so mundane.

In July 2015, attorney Elizabeth Beck told CNN’s Alisyn Camerota that Trump a few years earlier had suffered an “absolute meltdown” after she requested a break to pump breast milk.

“He got up,” Beck said, “his face got red, he shook his finger at me and he screamed, ‘You’re disgusting, you’re disgusting,’ and he ran out of there.”