Donald Trump is a winner. Just ask him. He won’t boast about failed business ventures, but he also can’t deny them. This isn’t an attack on the guy running for POTUS. Clearly, he is running one of the craziest, most surreal and surprisingly successful campaigns in American political history. However, there’s another side to this coin boasting the bust of The Donald. Not everything goes as Donald plans—not even when he’s 100% sure something will be a wild success. Here are 12 examples of Donald Trump’s oopsies.

12. Trump Shuttle (Airlines)

In the late 1980s, The Donald decided he’d give the airline industry a go, and purchased a very successful commuter line, Easter Air Shuttle. The small airline offered east coast travel to Boston, Washington D.C. and New York City. At the time Donald purchased the airline, the company had enjoyed a solid, 27 year track record of simple, east coast link, with no frills and a fast, convenient, fairly priced commute. The Donald thought, “Hey, these east coasters are highfalutin, what they want is faux luxury.” So, Donald turned the airline into Trump Shuttle, painted big Ts on the tails, decked out the cabins with luxury materials, and even inlaid the bathrooms with gold and premium fixtures. Along with the increase in amenities came an increase in price. By 1992, Donald had defaulted on his loans and the airline went kaput.

11. Trump Fashion Line

Was this a failure, or a moderate success? It is still selling, so we’ll agree that it is making some coin. But how is Donald maximizing his profits on his clothing line? All his crap is manufactured in China and Mexico. Not to put the guy in the corner with the dunce cap, but how about the one labeled hypocrite? Here’s the deal: Donald would have everyone believe that his brand should be on the shelves, and hanging from the racks of the stuff he actually wears. Not even close. Donald may have personal suits that boast his label, but make no mistake, he’s wearing custom garb. The first thing you do as a billionaire is have all of your stuff tailored. So, what does that mean for the future of Donald’s clothing line if he walls off Mexico, and sticks it to China?

10. Trump Vodka

Trump and Tonic, anyone? Love him or hate him, Donald Trump will stand firm behind his ideas, even if he knows they’re terrible, and he’s relegated to simply selling a service or product. Such was the case with Donald’s foray into the beverage industry with Trump Vodka. The slogan: Success Distilled. Sadly for Donald, this hit with the force of distilled water, and the vodka brand didn’t last a full five years. Why did Donald think the world would want to drink his vodka? Well, really, he just wanted to mix up the business competition with his “friends” at Grey Goose (Grey Goose being more overrated than any vodka on the market…it proves people will believe anything if you price it high enough). Donald predicted Trump and Tonic would become a very popular drink in high-end restaurants, bars and social functions. Nope.

9. Trump Entertainment Resorts

When you think of gambling away your child’s college fund, think Trump Casinos! What exactly are Trump Casinos? They’re a company officially under the umbrella of Trump Entertainment Resorts in Atlantic City, New Jersey, which have filed for bankruptcy protection four times. According to Donald, the entities bear his name because of his influence, but as a businessman he only holds stake in the company, and has nothing to do with the day-to-day operations of any of the facilities. Obviously. If Donald were in charge, these locations would be wildly successful—like the Wynn properties in Las Vegas. In reality, Donald can attempt to distance himself from the failed entity as much as he likes, but he owns 28 percent of the stake. When you own more than a quarter of a company, it’d only make sense you’re offering some input.

8. Trump The Game

Here comes the first Donald double whammy. And this isn’t a knock on the guy. If you had a chance to market a board game with your personal brand attached, how could you not give it a go? For Donald, he tried to market a board game entitled Trump the Game in the late 1980s, but it didn’t sell. It was too much like the classic Monopoly, and it doesn’t matter who you are: you’re not competing with Monopoly. Some 25 years later, Donald decided to give board gaming another go, following up on the success of The Apprentice. They used the same model of the game that didn’t sell in 1989, and surprise, surprise, The Apprentice version also sold a few sets, then was promptly discontinued. How much money was lost on these ventures is up for wild guess. Surely, the games were manufactured in China.

7. Trump Mortgage

How easy is it to dupe Donald Trump? His mortgage venture is alarming and disconcerting. It’s a sign that Donald really does delegate, and allow “his people” to do their thing. If they don’t, he gives them the boot. Trump Mortgage was another Donald misadventure. The fruit of popularity from The Apprentice. Seriously, Donald put his name on a mortgage company in 2006, and hired E.J. Ridings as CEO, a man who claimed to have an illustrious investment banking career, but in reality had only worked on Wall Street for a week as a broker. At least the guy was registered. Eighteen months later, Trump Mortgage ceased to exist due to poor management, and a general lack of knowing how to run a mortgage company. In fairness, E.J. had skill, he simply didn’t have the clout to lead, regardless of the Trump name.

6. Trump Fragrances

When you think smelling your best, you probably think Aqua Di Gio by Armani, or Bleu de Chanel. What you don’t think: Donald Trump. Again, love him or hate him for his politics, there is nothing about the guy that makes you want to get up close and have a sniff. He doesn’t exude scent-sationalism, rather sensationalism. The difference between the two is staggering. We have to offer Donald props for the fact that his fragrances are still selling to retailers, and imaginably, flying off the shelves. There are three options to choose from: Donald Trump, Success, and Empire. Empire is so fine, it goes for more than 50 bucks per bottle. And because we can’t make this up—the smell of Success: “Top notes of coriander, iced red currant, and juniper with middle notes of bamboo leaf and geranium with a base of birch wood, musk, tonka bean and vetiver.”

5. GoTrump.com

Have you even heard of GoTrump.com? It was a luxury travel website that was powered by Travelocity. You can’t deny Donald’s ability to network. We just saw a bunch of pastors and a rabbi praying over him the other day. The guy scores connections with the lucrative lure of financial prosperity, even if there’s no way he can make good when he reels in the line. GoTrump.com was launched in 2006, pretty much due to the popularity of The Apprentice. The guy knows how to milk a cash cow. The service was to provide luxury travel options and amenities to people who are shopping for travel and vacations online in an effort to score the best possible deal. We’re starting to think Donald might surround himself with “Yes Men.” While other investments make logical sense, this one…? What’s difficult about buying first class airfare on Priceline.com?

4. Trump Magazine

Who did Donald think he was…Oprah? In 2007—yes, once again, banking on the success of The Apprentice—Donald threw another iron into the fire, this time in the form of a publication. Not to be confused with the original Trump magazine, the cult, late 1950s magazine that died before it started because it took shots at big publishers like Hugh Hefner, Trump Magazine was a Donald idea that was pandering to wannabe affluent types who could only appreciate what was between its two glossy covers. According to the press release that served to launch the magazine, it focused on reflecting the “passions of its affluent readership by tapping into a rich cultural tapestry.” And by that, we take it to mean the magazine had no focus and contained a lot of ads. After those contracts ended with advertisers, so did the magazine, one year later.

3. Trump University

Is this real life? Again…milking the cash cow, The Apprentice, Donald Trump thought it would be a good idea to get into the big business of education. Private education—unaccredited…private education. In 2005, Donald “opened” Trump University, and surprisingly, it enjoyed a small enrollment for five years before students started complaining. Apparently, the classes amounted to little more than “informercials.” What these students thought they would get from an unaccredited institution, who knows? Either way, they sued, and Donald changed the name of the institution to The Trump Entrepreneur Initiative. They killed its operations a year later. In 2013, the New York Attorney General’s Office sued Donald and the university for fraud…to the tune of $40 million. This suit is still in process, and the court has announced that it will proceed. That might throw a wrench into any presidential plans.

2. Trump Steaks

This has to be a joke, right? In 2007, while Donald was enjoying the fruits of his empire in the form of a soon-to-fail magazine, mortgage business, vodka and university, he decided he’d go whole hog, open a steakhouse restaurant, and also offer mail order steaks—the best steaks in the world. Hey, it has worked well for Omaha Steaks, why wouldn’t it work for The Donald? Well, here’s one reason: In 2012, Donald’s Las Vegas steakhouse was hammered by the health department and was closed due to 51 health code violations. One of the most glaring…? Serving duck that had been delivered some 150 days prior. When Donald was interviewed to push his mail order steaks, he had this to say, “One bite and you’ll know exactly what I’m talking about. And believe me: I understand steaks. They’re my favorite food.”

1. The USFL

There is nothing like competition to breed excellence: this was the hope of the United States Football League, and the league founder, David Dixon. For those who are too young to really remember the USFL, it was a professional football league that offered players an alternative to playing in the NFL. The league played for three seasons, from 1982-1986, and attracted some of the best talent coming out of college, including Herschel Walker, Jim Kelly and Boston College standout, Doug Flutie. To avoid direct competition with the NFL, the USFL played its games in the spring. Donald Trump infamously owned the NYC area team, the New Jersey Generals, and he is most often fingered for the league’s demise. He championed a move to the fall, brazenly stating, “If God wanted football in the spring, he wouldn’t have created baseball.” In effect, the move killed the league.