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15 Ugly CEOs With Smoking Hot Daughters

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According to TIME Magazine, CEOs with daughters score higher in tests on “corporate social responsibility” metrics such as diversity, community, employee relations, product, environment, and human rights. That’s good news for the major global companies headed up by some of the following men, because they do have daughters, and their daughters are hot. Really hot. Unbelievably hot, because these CEOs have some pretty ugly mugs to look at in the mirror every morning. It is truly by some miracle of genetics that such ugly men can have such beautiful daughters.

At this point, there’s no scientific research into any possible correlations between a company’s social responsibility metrics and the attractiveness of the CEOs daughter, but if a positive correlation were to be discovered, it would mean that Green Peace and the Nobel Prize committee can step aside, because Bloomberg, Microsoft, Apple Inc, Dell, Hilton, Virgin Group, and the Trump Organization among others are easily the most socially responsible organizations to ever exist!

15. Richard Hilton and Paris Hilton

Who has f— you money? Richard Hilton has f— you money. He’s the grandson of the man who started the hotel chain that bears their name, and with a net worth of $300 million, from his real estate brokerage firm, he’s a chip right off the old block. Lucky for him, because he’s one ugly dude.

There’s different variations of ugly, like hideously ugly and medically ugly, well Richard Hilton is the dorky kind of ugly. He looks like the unfortunate love child of Quentin Tarantino and Screech from Saved by The Bell. But his daughter, Paris, on the other hand, is absolutely gorgeous.

She’s done well for herself too, as a reality television personality, though many critics say she is the epitome of someone who is “famous for being famous,” and cite how her show The Simple Life was helped along by the release of the sex tape with the best name any sex tape has ever had: “One Night in Paris.”

14. Michael Bloomberg and Georgina Bloomberg

Michael Bloomberg is a billionaire business magnate and served as Mayor of New York City from 2002 – 2013. He made his money in financial data and media. He became mayor of New York City in the immediate aftermath of the 9/11 terrorist attacks, and presided over a balanced agenda of progressive social policy and conservative fiscal policy.

The man is very rich, powerful, and famous, but he’s not exactly a male model. Though his daughter, Georgina Bloomberg, could be a model if she wanted to be.

Georgina (born 1983) is not, however, a model. She’s a professional equestrian, that is she rides horses for a living. Of course, she probably doesn’t have to do anything for a living, but she does ride horses for sport, earning a corporate sponsorship with Ariat International.

She’s good friends with Ivanka Trump, and has gone on the record to say many kind things about Donald Trump and what a great father he is, and how proud Georgina is of his accomplishments.

13. Bill Gates and Jennifer Katharine Gates

Bill Gates. He won. He just plain won. What does DJ Khaled say? “All I do is win.” Nah, man. You’re cool, make no mistake, and we all love you, but you do not win. Bill Gates wins. Maybe no one in the history of this planet has won as much as this nerdy kid from Washington.

Nerdy, yeah. Also fiercely, viciously, cut-your-throat ambitious to climb to the top of an industry that he knew was going to dominate the planet. So ambitious in fact, that he was willing to make a deal with Satan that he’d get to be the richest man in the world, but that he’d have to look like a turtle for the rest of his life.

Did you even know Bill Gates has a daughter? I didn’t either until I started writing this article. I was like: Oh snap! Bill Gates has a daughter. Oh snap! She’s gorgeous. She must be getting that from Melinda.

12. Steve Jobs and Eve Jobs

Who’s your daddy? Steve Jobs is your daddy. You’re probably reading this on a device his company designed and manufactured. This man created the most valuable company in the world. They’ve got just literally billions and billions of dollars cash on hand, just sitting in bank accounts.

The late Jobs wasn’t as slick a business man as Gates, but a way slicker designer. His stated goal with his design team in creating the iPhone, was to make something that looked so sexy, that people would want to lick the icons off the screen.

Was Steve Jobs ugly? You be the judge. This picture of him above is off of his authorized biography, so it’s pretty much the best he could muster. Look, there are worse looking CEOs on this list, but it’s still a marvel of nature that the beautiful young lady pictured on the left sprang forth from that caveman’s loins.

Yes, Steve Jobs actually has a daughter named Eve Jobs. No joke. And as you can see above, she hangs with Bill Gates’ daughter. The two take their fathers’ rivalry onto the sporting range with horse competitions.

11. Michael Dell and Alexa Dell

Michael Dell once called and scheduled a test proctor to come to his house and administer tests for him to get his GED so he could skip high school and move on with life. He was eight years old at the time.

A sign of things to come, Dell was so successful selling phonebook subscriptions in high school, he used the money to buy a brand new white BMW and drove that to college with a bunch of computers and computer parts, where he promptly dropped out after the first semester. He was making too much money selling computers to keep doing college.

But you can’t win ’em all. Michael Dell, who hails from Texas, is a slightly better looking George W. Bush. That’s the best you can say about him.

His daughter Alexa, on the other hand, is stunning. She’s made a lot of headlines for apparently compromising her family’s security by inadvertently tweeting their locations and for dating the CEO of Tinder.

10. Bernie Ecclestone and Petra Ecclestone

Bernie Ecclestone, have you heard of this guy? Dude is what they call a magnate. Net worth is $3.1 billion (USD). That’s a lot of cat wax. How’d he make all that money? Bernie Ecclestone was the CEO of the Formula One Group, which owns and manages Formula One racing.

And yeah, Mr. Ecclestone is, to say the least, ugly as sin itself. He looks like he fell off the ugly tree and hit every branch on the way down. I mean there’s ugly, and then there’s Bernie Ecclestone ugly, and Bernie Ecclestone ugly is something gone horribly, terribly wrong.

So how on earth? Look at the two people pictured above. The one on the right is 50% derived from the one on the left. How the actual hell is that possible? When her husband makes out with the lovely Petra Ecclestone Stunt, he’s making out with 50% of Bernie. Somehow. It just defies all reason, science, and philosophy combined.

She has extravagant tastes, got married in a $15 million wedding, and lives in an $85 million dollar home in Los Angeles, and a $90 million home in London.

9. Bernie Ecclestone and Tamara Ecclestone

There’s no way he pulled that off twice! But he did. He actually had another hot daughter in a winning streak of genetic oddity that should be studied by science. His daughter Tamara is absolutely gorgeous.

He’s so ugly, he could have been one of the scary people in the Home Alone movies that Kevin McCallister has to realize isn’t evil just because they’re so bad looking that they’re seriously terrifying.

What more is there to say about Bernie? Is there anything uglier than Mr. Ecclestone’s looks? Yes. There actually is. His views about women and Hitler. Speaking about IndyCar racer Danica Patrick, he said, “You know I’ve got one of those wonderful ideas… women should be dressed in white like all the other domestic appliances.”

In a 2009 interview with the Times, he had this to say: “Terrible to say this I suppose, but apart from the fact that Hitler got taken away and persuaded to do things that I have no idea whether he wanted to do or not, he was – in the way that he could command a lot of people – able to get things done.”

8. Bud Walton and Elizabeth Paige Laurie

James “Bud” Walton was the brother of Sam Walton and co-founder of Walmart. Ever heard of it?

Those guys are so rich from that little retail outfit that started in a bean field in Bentonville, Arkansas, that if you look at the Forbes list of richest people in the United States, Walton heirs make up half the top ten after splitting all the money up amongst themselves!

It’s truly unreal. But not as unreal as the fact that the cute, sassy thing you see pictured on the right is actually the granddaughter of the ugly old man you see pictured on the left. She’s like a tall glass of sweet iced tea. He’s like a sip of water from the creek.

Back in 2005, she had to return her degree to University of Southern California after a student made allegations that Laurie paid her $20,000 to do her homework. When she filed for divorce from her husband in 2015, citing irreconcilable differences, he claimed he would need $400,000/month to maintain the lifestyle he had become accustomed to.

7. David Rockefeller Jr. and Ariana Rockefeller

The great grandson of great American oil baron, John D. Rockefeller, David Rockefeller Jr. sits on the many boards of the Rockefeller family’s various institutions and of course, is a member of the elite and secretive Bohemian Club and the Council on Foreign Relations, the New York City-based think tank whose research supports globalist hegemony.

He looks like a pallid, sad Papa Smurf. On a scale of 1 to 10 of man attractiveness, I am not just saying this to be mean, he’s a 1. Objective reporting. Somehow, the lovely girl with the model looks you see pictured above emerged from the womb of the poor woman David impregnated.

In her early thirties, Ariana is among the latest generation of Rockefellers, with big expectations of them by their elders. While her namesake ancestor made the Rockefeller name famous drilling for and distributing oil to the Industrial Revolution, Ariana is going to make a name for herself in fashion.

6. Donald Trump and Ivanka Trump

Donald Trump has already had great television experience playing a no-nonsense capitalist on The Apprentice, so the role he’s currently playing is perfect for him.

Trump is now CEO of the entire United States, but before that he was CEO of the Trump Organization, with billions of dollars in marketing and real estate holdings. So he’s definitely qualified to be on this list in terms of being a CEO. And he’s supremely qualified to be on this list for being ugly. In a perfect world, we would all look as ugly or beautiful on the outside as we are on the inside. So technically, Trump’s corner of the world is actually perfect. Because this miserable, gloating, petty billionaire, who never laughs and seldom cracks a smile, has a pitiably ill-proportioned face that for some reason just seems… crusty.

But through some stroke of good luck, his glamorous daughter, Ivanka Trump, dodged a seriously dangerous ugly bullet. Just imagine Donald’s face with long hair and some makeup. Now check out Ivanka. You know she’s grateful every day of her life she turned out like she did.

5. Donald Trump and Tiffany Trump

Never in the spotlight until the recent election of her father to the White House, Tiffany Trump is also incredibly lucky to look the way she does with a father that looks the way Donald Trump does.

There’s something about his wispy hair and the complexion of his skin. He looks like one of those biology textbook pictures of a dust mite up close under a microscope. The man is hideously, tragically ugly.

A frequent poster to Instagram, with over 750,000 followers, Tiffany Trump released a single in 2014 and told Oprah Winfrey she was considering whether to try to take her musical career to the next level.

With her father in the White House, and having recently graduated with her undergrad degree from the University of Pennsylvania, Tiffany has now set her sights on law school.

4. Richard Branson and Holly Branson

Sir Richard Branson, a billionaire many times over from his conglomerate that began in the 1970s as Virgin Records and expanded to include Virgin Airlines and many other businesses, is a remarkable man. He’s also remarkably ugly.

Being charitable, Branson looks like an albino chimpanzee with down syndrome. Or some kind of alien reptoid / mammal hybrid. His eyes are weirdly far apart on his head, and his sloping forehead really makes him look like a neanderthal or something.

But all jokes aside, how the hell does someone go from a retail store that sells records to just starting an airline? Bit of a jump isn’t it? And he’s so good at both that he’s a billionaire. And tops it all off by not passing on his ugly genes to his daughter.

Holly Branson, who already has kids of her own, two toddler twins, is cute as a button. And has such a friendly, approachable demeanor to her smile. So lovely. So lucky she doesn’t look a thing like dad.

3. Ralph Lauren and Dylan Lauren

Ralph Lauren, the New York fashion icon, with a multi-million dollar global brand of clothing that bears his name, is not much of a looker. Sure, he looks glamorous in any picture you’ve ever seen of him. He is glamorous. But that doesn’t mean he’s not ugly.

Just look at that picture above. The man is seriously running a looks deficit. “Aww, come on, that’s an old picture.” Calm down. Exactly. It’s an old picture because I wanted to give him a fighting chance in this, and show a young Ralph Lauren. This is him at his best. Golden age of his life and all. And he looks like a science experiment combined ET and the actress that played Carol Brady.

His daughter, Dylan Lauren, on the other hand is still smoking hot into her 40s. She’s the CEO of her own little business, Dylan’s Candy Store in New York City, which claims to be the largest candy store in the world. She had the inspiration for the store when she was five years old and saw Willy Wonka and the Chocolate Factory.

2. Stanley Ho and Josie Ho

Ever heard of Stanley Ho? You’re looking at him. You’d be laughing like that too if you’d made $2 billion (USD) off a gambling empire in China, lived to be 95 years old (he’s still alive, going for that triple digits!), and still had four wives decades after Hong Kong banned polygamy in the 70s.

How does a Chinese guy end up with a name like Stanley? Pay attention. I said he was from Hong Kong, mate. Lots of English influence in that neck of the woods. After building his business up from gambling, he naturally grew it to massive proportions on entertainment, tourism, real estate, and shipping.

That is actually one of his better looking pictures I selected for this article. The man is seriously giving Donald Trump and Bud Walton a run for their money on ugliness. But his youngest daughter, Josie Ho, a singer and actress, is drop dead stunning. Her eldest sister, a no-nonsense business woman, who followed in Stanley’s footsteps, encouraged her singing career over Stanley’s objections.

1. Paul Tudor and Caroline Jones

Paul Tudor Jones II is worth $4.7 billion off of the Tudor Investment Corporation, his hedge fund management company. Want to know what it takes to be a billionaire?

This guy Paul Tudor Jones actually dropped out of Harvard Business School thinking they wouldn’t be able to teach him what he really needed to know to make it in investing. He packed up, moved to New York and found a commodities trader who mentored him in trading cotton futures on the New York Stock exchange.

Smart, ballsy guy. Also ugly. Too ugly to have a daughter as beautiful as Caroline Jones without doing some kind of voodoo rituals to invoke beauty spirits over the bed where Caroline was conceived. Or something. He’s lucky he’s got his wife Sonia there to even out all his rough edges.

Caroline isn’t just a beautiful face. She’s got a beautiful voice. Sing on, Caroline! We’re rooting for you!

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