28 years of Donald Trump insulting women

1988
Ivana Trumpformer fashion model and first wife of Donald Trump
$1 a year plus all the dresses she can buy.
How Trump paid his wife's salary when he put her in charge of the Plaza Hotel (New York Times)
1990
Ivana Trumpformer fashion model and first wife of Donald Trump
I would never buy Ivana any decent jewels or pictures. Why give her negotiable assets?
Trump during the early years of his marriage to Ivana (Vanity Fair)
Ivana and Donald Trump at the Met Gala in 1985
Tom Gates/Getty Images
early '90s
Jill Harthpageant promoter
Are you sleeping with her?
Trump stared at a pageant promoter throughout a meeting and then asked her boyfriend and co-worker if she was sexually available. (Harth says Trump later sexually assaulted her; Trump claims Harth pursued him.) (New York Times)
1992
Gail CollinsNew York Times columnist
The Face of a Dog!
Trump's response to a column in Newsday calling him a "financially embattled thousandaire" (New York Times)
mid-'90s
Barbara Resconstruction executive
Not her.
Trump sent back an employee who was supposed to take lunch orders because she wasn't pretty enough (New York Times)
Barbara Res was a longtime employee of Donald Trump
New York Daily News
Barbara Resconstruction executive
You like your candy.
Trump's remark on a construction executive who'd gained weight working for him (New York Times)
1996
Jodie SealMiss Australia 1996
Suck your stomach in. Suck your gut in.
How Trump commented on the body of a beauty pageant contestant (Interview with Inside Edition)
1997
Brook Antoinette Mahealani LeeMiss Universe 1996
Don’t you think my daughter’s hot? She’s hot, right?
Trump asked the reigning Miss Universe about his daughter Ivanka, then 16 (New York Times)
Alicia MachadoMiss Universe 1996
We've tried diet, spa, a trainer, incentives. ... Forget it, the way she's going she'd eat the whole gymnasium.
Trump on Alicia Machado when she gained weight as Miss Universe (Newsweek )
Trump kissing Machado on the cheek during one of her workouts
Jon Levy/AFP/Getty Images
Princess DianaPrincess of Wales
I have only one regret in the women department — that I never had the opportunity to court Lady Diana Spencer ... a dream lady.
 (The Art of the Comeback)
2000
Princess DianaPrincess of Wales
She had the height, she had the beauty, she had the skin – the whole thing. … She was crazy, but these are minor details.
Trump on The Howard Stern Show discussing how much he'd like to sleep with Princess Diana, who had died three years earlier (BuzzFeed)
Princess Diana
Anwar Hussein/Getty Images
2004
Kristi FrankThe Apprentice contestant
You mean the one with the [gesture to indicate breasts]
How Trump referred to a contestant he was deciding whether to fire on The Apprentice. "He didn't even know her name," producer Katherine Walker said. (Associated Press)
mid-2000s
Rebecca ArndtThe Apprentice camera operator
There is a beautiful woman behind that camera, so I only want to look at that.
How Trump would talk to camera operators on The Apprentice (Associated Press)
2005
Nicollette Sheridanactress
A person who is very flat-chested is very hard to be a 10.
Trump on The Howard Stern Show, rating the beauty of the actors on ABC's Desperate Housewives (BuzzFeed)
Marcia Cross, known for her role on Desperate Housewives
Jon Kopaloff/Getty Images
Marcia Crossactress
Would you go out with Marcia Cross, or would you turn gay, Howard?
Trump on The Howard Stern Show, rating the beauty of the actors on ABC's Desperate Housewives (BuzzFeed)
mid/late 2000s
Maral Bolsajianwaitress at Trump National Golf Club
How's my favorite girl. … Are you still happily married?
How Trump would greet a waitress, who described herself as a "grown woman in her 40s," at his golf club (Los Angeles Times)
Nancy O'Dell, then Access Hollywood co-host
Jeff Kravitz/Getty Images
Nancy O'DellAccess Hollywood co-host
I did try and fuck her. She was married. I moved on her very heavily. In fact, I took her out furniture shopping. … I moved on her like a bitch, but I couldn’t get there and she was married… Then all of a sudden I see her, she’s now got the big phony tits and everything.
Trump commenting on O'Dell to her co-host Billy Bush on leaked audio from Access Hollywood (Washington Post)
2006
Nicole [last name unknown]waitress at Trump National Golf Club
See, you don't have to go to Hollywood to find beautiful women. … Do you like Jewish men?
How Trump introduced another waitress to a table of guests at his golf club (Los Angeles Times)
Rosie O'Donnell and then-wife Kelli Carpenter
Mathew Imaging/Getty Images
Rosie O'Donnellcomedian
Can you imagine the parents of Kelli ... when she said, ‘Mom, Dad, I just fell in love with a big, fat pig named Rosie’? Can you imagine the expression on their face?
How Trump talked about Rosie O'Donnell's relationship during their ongoing feud (Fox News)
Rosie O'Donnellcomedian
Rosie’s a loser. A real loser. I look forward to taking lots of money from my nice fat little Rosie.
Rosie O'Donnellcomedian
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 O'Donnell and fellow hosts of The View
ABC
Sue Kwiatkowskirestaurant manager at the Trump National Golf Club in Rancho Palos Verdes until 2009
I want you to get some good looking hostesses here. People like to see good looking people when they come in.
How Donald Trump hired waitresses for his golf club (Los Angeles Times)
Angelina Jolieactress
She's been with so many guys she makes me look like a baby, OK. … And, I just don't even find her attractive.
Trump criticizing Angelina Jolie's treatment of her father (Larry King Live)
Ivanka Trump
Andy Katz/Pacific Press
Ivanka TrumpDonald Trump's eldest daughter
If Ivanka weren’t my daughter, perhaps I’d be dating her.
Trump later said this comment was a joke. (The View)
2007
Rosie O'Donnellcomedian
She came to my wedding. She ate like a pig. And — I mean, seriously, the wedding cake was — was — it was, like, missing in action.
Trump to Larry King in 2007 (Larry King Live)
Angelina Jolieactress
Angelina Jolie is sort of amazing because everyone thinks she's like this great beauty. And I'm not saying she's an unattractive woman, but she's not a beauty, by any stretch of the imagination. I really understand beauty. And I will tell you, she's not — I do own Miss Universe. I do own Miss USA. I mean I own a lot of different things. I do understand beauty, and she's not.
How Trump described Angelina Jolie to Larry King in 2007 (Jezebel)
Angelina Jolie at the 2007 Cannes Film Festival
Tony Barson/Getty Images
Gloria Allredlawyer
I think Gloria would be very very impressed with [my penis].
Trump on TMZ after Gloria Allred sued him on behalf of a transgender woman barred from the Miss Canada pageant. Allred had said Trump didn't have to show his genitals to prove his sex. (TMZ)
Gloria Allred
Gregg DeGuire/Getty Images
2008
Anne Hathawayactress
She hasn’t remained very loyal to him, has she? So when he had plenty of money, she liked him, but then after that, not as good, right?
Trump in an Access Hollywood interview commenting on Anne Hathaway, whose ex-boyfriend had just been arrested on fraud charges (ABC News)
2009
Miss Universe contestants
Tell me, who’s the most beautiful woman here? … I don’t care if she’s sweet. Is she hot?
How Trump addressed the Miss Universe contestants, according to Carrie Prejean's book. (Trump says he never asked them to rate each other.) (New York Times)
Miss Universe 2009 and other contestants at a charity event
Marcel Thomas/Getty Images
2010
Mahsa Saeidi-AzcuyThe Apprentice contestant
Who’s the most beautiful on the women’s team?
Trump to male contestants on The Apprentice, according to a woman who competed (New York Post)
Maria NgoReporter for The Strip View Live
You wouldn't have your job if you weren't beautiful. It's very sad, isn't it?
Trump explaining to a reporter why beauty is important in beauty pageants (VegasNet TV)
2011
Brande RoderickFormer Playboy playmate, Celebrity Apprentice contestant
It must be a pretty picture. You dropping to your knees.
Trump's response when told that a contestant was so desperate to stay on the show she'd gotten on her knees to plead (Mediaite)
Brande Roderick
Carley Margolis/Getty Images
Elizabeth Becklawyer who deposed Trump
You're disgusting, you're disgusting.
How Trump reacted to a lawyer saying she needed to breastfeed, according to her deposition (Trump disputes her version of events) (CNN)
Rosie O'Donnellcomedian
I feel sorry for Rosie's new partner in love whose parents are devastated at the thought of their daughter being with @Rosie — a true loser.
2012
Bette Midlersinger
While @BetteMidler is an extremely unattractive woman, I refuse to say that because I always insist on being politically correct.
Trump and Bette Midler started a Twitter feud in 2012 that led Trump to attack her appearance (Twitter)
Bette Midler
NBC
Bette Midlersinger
.@BetteMidler talks about my hair but I'm not allowed to talk about her ugly face or body — so I won't. Is this a double standard?
Trump and Bette Midler started a Twitter feud in 2012 that led Trump to attack her appearance (Twitter)
Kristen Stewartactress
Robert I'm getting a lot of heat for saying you should dump Kristen — but I'm right. If you saw the Miss Universe girls you would reconsider.
Trump was insistent in 2012 that Robert Pattinson and Kristen Stewart should break up, firing off a string of tweets criticizing Stewart's looks and her infidelity (Twitter)
Kristen Stewart and then-boyfriend Robert Pattinson
Luca Teuchmann/Getty Images
Chersinger
@cher should spend more time focusing on her family and dying career.
Arianna Huffingtonco-founder and editor in chief of the Huffington Post
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.
2013
Beyoncésinger
When Beyoncé was thrusting her hips forward in a very suggestive manner, if someone else would have done that it would have been a national scandal. I thought it was ridiculous. … I thought it was not appropriate.
Trump comments on Beyoncé's 2013 Super Bowl performance on The Howard Stern Show (The Howard Stern Show)
Beyoncé, 2013 Super Bowl halftime performance
Kevin Mazur/Getty Images
Kim KardashianTV personality
She's really a nice person. She's gotten a little bit large. I don't think you should dress like you weigh 120 pounds.
Trump on Kim Kardashian during her pregnancy (Showbiz Tonight)
Kim KardashianTV personality
Does she have a good body? No. … Does she have a fat ass? Absolutely.
Trump on Kim Kardashian during her pregnancy (The Howard Stern Show)
Kim Kardashian
Gisela Schober/Getty Images
2014
Kim KardashianTV personality
Well, absolutely. [Her butt] is record-setting. … In the old days, they'd say she has a bad body.
Trump on Kim Kardashian's looks (The Howard Stern Show via Entertainment Tonight)
Chersinger
I promise not to talk about your massive plastic surgeries that didn’t work.
Trump after Cher referred to his trademark hairstyle as a "rug." "It's mine," he tweeted. (Twitter)
Rosie O'Donnellcomedian
Sorry, @Rosie is a mentally sick woman, a bully, a dummy and, above all, a loser. Other than that she is just wonderful!
Gail CollinsNew York Times columnist
There are many editorial writers that are good, some great, & some bad. But the least talented of all is frumpy Gail Collins of NYTimes.
Gail Collins
Jeffrey Ufberg/Getty Images
Rosie O'Donnellcomedian
Rosie is crude, rude, obnoxious and dumb — other than that I like her very much!
Chersinger
.@tedcruz must be doing something right if @cher, sadly rated the 4th ugliest celebrity according to @listverse, is attacking him.
2015
Arianna Huffingtonco-founder and editor in chief of the Huffington Post
Why is it necessary to comment on .@ariannahuff looks? Because she is a dog who wrongfully comments on me.
Arianna Huffington
Mike Pont/Getty Images
Arianna Huffingtonco-founder and editor in chief of the Huffington Post
How much money is the extremely unattractive (both inside and out) Arianna Huffington paying her poor ex-hubby for the use of his name?
Megyn KellyFox News host
You could see there was blood coming out of her eyes, blood coming out of her wherever.
Trump after Megyn Kelly moderated the Republican debate (CNN)
Olivia Nuzzireporter
Very young and very beautiful.
How Trump greeted Daily Beast reporter Olivia Nuzzi (New York magazine)
Carly Fiorina, former 2016 Republican presidential candidate
NBC
Carly Fiorinaformer CEO of Hewlett-Packard and 2016 Republican presidential candidate
Look at that face! Would anyone vote for that? Can you imagine that, the face of our next president?
Trump comments to a Rolling Stone reporter about Carly Fiorina's appearance on TV (Rolling Stone)
Heidi Klummodel
Sadly, she’s no longer a 10.
Trump to the New York Times's Maureen Dowd, while trying to explain that he can be diplomatic (New York Times)
2016
Ghazala KhanGold Star mother of Capt. Humayun Khan
Maybe she wasn’t allowed to have anything to say.
Trump speculates on why Ghazala Khan didn't speak when standing next to her husband at the DNC. Khan later said she was too upset by her son's death to speak about it publicly. (ABC News)
Alicia MachadoMiss Universe 1996
She was the worst we ever had, the worst, the absolute worst, she was impossible. She gained a massive amount of weight, and it was a real problem.
Trump after Clinton mentioned Alicia Machado (Fox News)
Heidi Cruz at a rally for her husband, Ted Cruz
Jim Watson/Getty Images
Heidi Cruzwife of Ted Cruz
No need to ‘spill the beans’ the images are worth a thousand words.
Trump retweeting an unattractive photo of Heidi Cruz (Twitter)
Mika Brzezinskijournalist
@morningmika is off the wall, a neurotic and not very bright mess!
Trump on Morning Joe's Mika Brzezinski (Twitter)
Megyn KellyFox News host
I refuse to call Megyn Kelly a bimbo, because that would not be politically correct. Instead I will only call her a lightweight reporter!
Megyn Kelly and Donald Trump before Megyn Kelly Presents
Fox
Megyn KellyFox News host
She is so average in every way, who the hell wants to woo her!
Alicia MachadoMiss Universe 1996
Did Crooked Hillary help disgusting (check out sex tape and past) Alicia M become a U.S. citizen so she could use her in the debate?
1988
Ivana Trumpformer fashion model and first wife of Donald Trump
$1 a year plus all the dresses she can buy.
How Trump paid his wife's salary when he put her in charge of the Plaza Hotel (New York Times)
1990
Ivana Trumpformer fashion model and first wife of Donald Trump
I would never buy Ivana any decent jewels or pictures. Why give her negotiable assets?
Trump during the early years of his marriage to Ivana (Vanity Fair)
Ivana and Donald Trump at the Met Gala in 1985
Tom Gates/Getty Images
early '90s
Jill Harthpageant promoter
Are you sleeping with her?
Trump stared at a pageant promoter throughout a meeting and then asked her boyfriend and co-worker if she was sexually available. (Harth says Trump later sexually assaulted her; Trump claims Harth pursued him.) (New York Times)
1992
Gail CollinsNew York Times columnist
The Face of a Dog!
Trump's response to a column in Newsday calling him a "financially embattled thousandaire" (New York Times)
mid-'90s
Barbara Resconstruction executive
Not her.
Trump sent back an employee who was supposed to take lunch orders because she wasn't pretty enough (New York Times)
Barbara Res was a longtime employee of Donald Trump
New York Daily News
Barbara Resconstruction executive
You like your candy.
Trump's remark on a construction executive who'd gained weight working for him (New York Times)
1996
Jodie SealMiss Australia 1996
Suck your stomach in. Suck your gut in.
How Trump commented on the body of a beauty pageant contestant (Interview with Inside Edition)
1997
Brook Antoinette Mahealani LeeMiss Universe 1996
Don’t you think my daughter’s hot? She’s hot, right?
Trump asked the reigning Miss Universe about his daughter Ivanka, then 16 (New York Times)
Alicia MachadoMiss Universe 1996
We've tried diet, spa, a trainer, incentives. ... Forget it, the way she's going she'd eat the whole gymnasium.
Trump on Alicia Machado when she gained weight as Miss Universe (Newsweek )
Trump kissing Machado on the cheek during one of her workouts
Jon Levy/AFP/Getty Images
Princess DianaPrincess of Wales
I have only one regret in the women department — that I never had the opportunity to court Lady Diana Spencer ... a dream lady.
 (The Art of the Comeback)
2000
Princess DianaPrincess of Wales
She had the height, she had the beauty, she had the skin – the whole thing. … She was crazy, but these are minor details.
Trump on The Howard Stern Show discussing how much he'd like to sleep with Princess Diana, who had died three years earlier (BuzzFeed)
Princess Diana
Anwar Hussein/Getty Images
2004
Kristi FrankThe Apprentice contestant
You mean the one with the [gesture to indicate breasts]
How Trump referred to a contestant he was deciding whether to fire on The Apprentice. "He didn't even know her name," producer Katherine Walker said. (Associated Press)
mid-2000s
Rebecca ArndtThe Apprentice camera operator
There is a beautiful woman behind that camera, so I only want to look at that.
How Trump would talk to camera operators on The Apprentice (Associated Press)
2005
Nicollette Sheridanactress
A person who is very flat-chested is very hard to be a 10.
Trump on The Howard Stern Show, rating the beauty of the actors on ABC's Desperate Housewives (BuzzFeed)
Marcia Cross, known for her role on Desperate Housewives
Jon Kopaloff/Getty Images
Marcia Crossactress
Would you go out with Marcia Cross, or would you turn gay, Howard?
Trump on The Howard Stern Show, rating the beauty of the actors on ABC's Desperate Housewives (BuzzFeed)
mid/late 2000s
Maral Bolsajianwaitress at Trump National Golf Club
How's my favorite girl. … Are you still happily married?
How Trump would greet a waitress, who described herself as a "grown woman in her 40s," at his golf club (Los Angeles Times)
Nancy O'Dell, then Access Hollywood co-host
Jeff Kravitz/Getty Images
Nancy O'DellAccess Hollywood co-host
I did try and fuck her. She was married. I moved on her very heavily. In fact, I took her out furniture shopping. … I moved on her like a bitch, but I couldn’t get there and she was married… Then all of a sudden I see her, she’s now got the big phony tits and everything.
Trump commenting on O'Dell to her co-host Billy Bush on leaked audio from Access Hollywood (Washington Post)
2006
Nicole [last name unknown]waitress at Trump National Golf Club
See, you don't have to go to Hollywood to find beautiful women. … Do you like Jewish men?
How Trump introduced another waitress to a table of guests at his golf club (Los Angeles Times)
Rosie O'Donnell and then-wife Kelli Carpenter
Mathew Imaging/Getty Images
Rosie O'Donnellcomedian
Can you imagine the parents of Kelli ... when she said, ‘Mom, Dad, I just fell in love with a big, fat pig named Rosie’? Can you imagine the expression on their face?
How Trump talked about Rosie O'Donnell's relationship during their ongoing feud (Fox News)
Rosie O'Donnellcomedian
Rosie’s a loser. A real loser. I look forward to taking lots of money from my nice fat little Rosie.
Rosie O'Donnellcomedian
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 O'Donnell and fellow hosts of The View
ABC
Sue Kwiatkowskirestaurant manager at the Trump National Golf Club in Rancho Palos Verdes until 2009
I want you to get some good looking hostesses here. People like to see good looking people when they come in.
How Donald Trump hired waitresses for his golf club (Los Angeles Times)
Angelina Jolieactress
She's been with so many guys she makes me look like a baby, OK. … And, I just don't even find her attractive.
Trump criticizing Angelina Jolie's treatment of her father (Larry King Live)
Ivanka Trump
Andy Katz/Pacific Press
Ivanka TrumpDonald Trump's eldest daughter
If Ivanka weren’t my daughter, perhaps I’d be dating her.
Trump later said this comment was a joke. (The View)
2007
Rosie O'Donnellcomedian
She came to my wedding. She ate like a pig. And — I mean, seriously, the wedding cake was — was — it was, like, missing in action.
Trump to Larry King in 2007 (Larry King Live)
Angelina Jolieactress
Angelina Jolie is sort of amazing because everyone thinks she's like this great beauty. And I'm not saying she's an unattractive woman, but she's not a beauty, by any stretch of the imagination. I really understand beauty. And I will tell you, she's not — I do own Miss Universe. I do own Miss USA. I mean I own a lot of different things. I do understand beauty, and she's not.
How Trump described Angelina Jolie to Larry King in 2007 (Jezebel)
Angelina Jolie at the 2007 Cannes Film Festival
Tony Barson/Getty Images
Gloria Allredlawyer
I think Gloria would be very very impressed with [my penis].
Trump on TMZ after Gloria Allred sued him on behalf of a transgender woman barred from the Miss Canada pageant. Allred had said Trump didn't have to show his genitals to prove his sex. (TMZ)
Gloria Allred
Gregg DeGuire/Getty Images
2008
Anne Hathawayactress
She hasn’t remained very loyal to him, has she? So when he had plenty of money, she liked him, but then after that, not as good, right?
Trump in an Access Hollywood interview commenting on Anne Hathaway, whose ex-boyfriend had just been arrested on fraud charges (ABC News)
2009
Miss Universe contestants
Tell me, who’s the most beautiful woman here? … I don’t care if she’s sweet. Is she hot?
How Trump addressed the Miss Universe contestants, according to Carrie Prejean's book. (Trump says he never asked them to rate each other.) (New York Times)
Miss Universe 2009 and other contestants at a charity event
Marcel Thomas/Getty Images
2010
Mahsa Saeidi-AzcuyThe Apprentice contestant
Who’s the most beautiful on the women’s team?
Trump to male contestants on The Apprentice, according to a woman who competed (New York Post)
Maria NgoReporter for The Strip View Live
You wouldn't have your job if you weren't beautiful. It's very sad, isn't it?
Trump explaining to a reporter why beauty is important in beauty pageants (VegasNet TV)
2011
Brande RoderickFormer Playboy playmate, Celebrity Apprentice contestant
It must be a pretty picture. You dropping to your knees.
Trump's response when told that a contestant was so desperate to stay on the show she'd gotten on her knees to plead (Mediaite)
Brande Roderick
Carley Margolis/Getty Images
Elizabeth Becklawyer who deposed Trump
You're disgusting, you're disgusting.
How Trump reacted to a lawyer saying she needed to breastfeed, according to her deposition (Trump disputes her version of events) (CNN)
Rosie O'Donnellcomedian
I feel sorry for Rosie's new partner in love whose parents are devastated at the thought of their daughter being with @Rosie — a true loser.
2012
Bette Midlersinger
While @BetteMidler is an extremely unattractive woman, I refuse to say that because I always insist on being politically correct.
Trump and Bette Midler started a Twitter feud in 2012 that led Trump to attack her appearance (Twitter)
Bette Midler
NBC
Bette Midlersinger
.@BetteMidler talks about my hair but I'm not allowed to talk about her ugly face or body — so I won't. Is this a double standard?
Trump and Bette Midler started a Twitter feud in 2012 that led Trump to attack her appearance (Twitter)
Kristen Stewartactress
Robert I'm getting a lot of heat for saying you should dump Kristen — but I'm right. If you saw the Miss Universe girls you would reconsider.
Trump was insistent in 2012 that Robert Pattinson and Kristen Stewart should break up, firing off a string of tweets criticizing Stewart's looks and her infidelity (Twitter)
Kristen Stewart and then-boyfriend Robert Pattinson
Luca Teuchmann/Getty Images
Chersinger
@cher should spend more time focusing on her family and dying career.
Arianna Huffingtonco-founder and editor in chief of the Huffington Post
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.
2013
Beyoncésinger
When Beyoncé was thrusting her hips forward in a very suggestive manner, if someone else would have done that it would have been a national scandal. I thought it was ridiculous. … I thought it was not appropriate.
Trump comments on Beyoncé's 2013 Super Bowl performance on The Howard Stern Show (The Howard Stern Show)
Beyoncé, 2013 Super Bowl halftime performance
Kevin Mazur/Getty Images
Kim KardashianTV personality
She's really a nice person. She's gotten a little bit large. I don't think you should dress like you weigh 120 pounds.
Trump on Kim Kardashian during her pregnancy (Showbiz Tonight)
Kim KardashianTV personality
Does she have a good body? No. … Does she have a fat ass? Absolutely.
Trump on Kim Kardashian during her pregnancy (The Howard Stern Show)
Kim Kardashian
Gisela Schober/Getty Images
2014
Kim KardashianTV personality
Well, absolutely. [Her butt] is record-setting. … In the old days, they'd say she has a bad body.
Trump on Kim Kardashian's looks (The Howard Stern Show via Entertainment Tonight)
Chersinger
I promise not to talk about your massive plastic surgeries that didn’t work.
Trump after Cher referred to his trademark hairstyle as a "rug." "It's mine," he tweeted. (Twitter)
Rosie O'Donnellcomedian
Sorry, @Rosie is a mentally sick woman, a bully, a dummy and, above all, a loser. Other than that she is just wonderful!
Gail CollinsNew York Times columnist
There are many editorial writers that are good, some great, & some bad. But the least talented of all is frumpy Gail Collins of NYTimes.
Gail Collins
Jeffrey Ufberg/Getty Images
Rosie O'Donnellcomedian
Rosie is crude, rude, obnoxious and dumb — other than that I like her very much!
Chersinger
.@tedcruz must be doing something right if @cher, sadly rated the 4th ugliest celebrity according to @listverse, is attacking him.
2015
Arianna Huffingtonco-founder and editor in chief of the Huffington Post
Why is it necessary to comment on .@ariannahuff looks? Because she is a dog who wrongfully comments on me.
Arianna Huffington
Mike Pont/Getty Images
Arianna Huffingtonco-founder and editor in chief of the Huffington Post
How much money is the extremely unattractive (both inside and out) Arianna Huffington paying her poor ex-hubby for the use of his name?
Megyn KellyFox News host
You could see there was blood coming out of her eyes, blood coming out of her wherever.
Trump after Megyn Kelly moderated the Republican debate (CNN)
Olivia Nuzzireporter
Very young and very beautiful.
How Trump greeted Daily Beast reporter Olivia Nuzzi (New York magazine)
Carly Fiorina, former 2016 Republican presidential candidate
NBC
Carly Fiorinaformer CEO of Hewlett-Packard and 2016 Republican presidential candidate
Look at that face! Would anyone vote for that? Can you imagine that, the face of our next president?
Trump comments to a Rolling Stone reporter about Carly Fiorina's appearance on TV (Rolling Stone)
Heidi Klummodel
Sadly, she’s no longer a 10.
Trump to the New York Times's Maureen Dowd, while trying to explain that he can be diplomatic (New York Times)
2016
Ghazala KhanGold Star mother of Capt. Humayun Khan
Maybe she wasn’t allowed to have anything to say.
Trump speculates on why Ghazala Khan didn't speak when standing next to her husband at the DNC. Khan later said she was too upset by her son's death to speak about it publicly. (ABC News)
Alicia MachadoMiss Universe 1996
She was the worst we ever had, the worst, the absolute worst, she was impossible. She gained a massive amount of weight, and it was a real problem.
Trump after Clinton mentioned Alicia Machado (Fox News)
Heidi Cruz at a rally for her husband, Ted Cruz
Jim Watson/Getty Images
Heidi Cruzwife of Ted Cruz
No need to ‘spill the beans’ the images are worth a thousand words.
Trump retweeting an unattractive photo of Heidi Cruz (Twitter)
Mika Brzezinskijournalist
@morningmika is off the wall, a neurotic and not very bright mess!
Trump on Morning Joe's Mika Brzezinski (Twitter)
Megyn KellyFox News host
I refuse to call Megyn Kelly a bimbo, because that would not be politically correct. Instead I will only call her a lightweight reporter!
Megyn Kelly and Donald Trump before Megyn Kelly Presents
Fox
Megyn KellyFox News host
She is so average in every way, who the hell wants to woo her!
Alicia MachadoMiss Universe 1996
Did Crooked Hillary help disgusting (check out sex tape and past) Alicia M become a U.S. citizen so she could use her in the debate?