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Donald Trump
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If there’s one thing celebrities love, it’s talking about themselves on social media and the brands they love — or love to hate. But what social media giveth, it can taketh away. One ill-timed tweet, photo, or status update can upset everything in a flash, embarrassing celebs and brands alike. These 12 famous folks learned that lesson the hard way.

DONALD TRUMP AND HARLEY-DAVIDSON

Harley-Davidson
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President Trump’s decision to impose tariffs on the European Union (and the EU’s tit-for-tat response) prompted motorcycle maker Harley-Davidson to announce in June that it would move some production overseas. Trump fired back on Twitter, suggesting in an Aug. 12 tweet that Harley owners were planning a company boycott in response. On Oct. 25, Harley-Davidson announced a third-quarter decline in sales of 13.3 percent from the same period last year. But profits rose over the same period, and while some economists say it’s doubtful Trump can be blamed, others say his tweets may have had a temporary impact on sales.

KATHY GRIFFIN AND SQUATTY POTTY

Kathy Griffin
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Comedian Kathy Griffin made her name with crass comments about famous folks just like Donald Trump. But it’s doubtful that the makers of the Squatty Potty, a toilet stool, expected anything like what happened in 2017 after they hired Griffin to tout their product. On May 30, after Griffin decided to post a photo of herself holding a bloody fake decapitated head of the president, things really hit the fan. A Twitter storm ensued, and Squatty Potty responded soon thereafter by firing Griffin.

KEVIN SMITH AND SOUTHWEST AIRLINES

Kevin Smith
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In 2017, director Kevin Smith did something he didn’t think he’d ever do: fly Southwest Airlines. In 2010, Smith (who freely admits to being overweight) says the airline booted him off a flight he was on as a standby passenger. Why? Because he was, he says, “too fat” to fit comfortably in one seat. Smith tweeted angrily about his experience and later recorded a podcast with a woman who suffered a similar fate. But two years later, Smith decided to fly Southwest again and tweeted the results. Southwest happily tweeted back.

DONALD TRUMP AND MACY’S

Donald Trump
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The president is no stranger to controversy or Twitter, as the entire Internet knows. Long before he was president, Donald Trump had inked a deal with Macy’s to sell a line of menswear branded with Trump’s name. After making disparaging remarks about illegal immigrants in 2015, Macy’s pulled the entire line from its stores that July. Trump quickly called for a boycott of Macy’s via Twitter. Was it effective? It’s hard to say, but Macy’s stock currently is trading for about half what it was at the time of the tweet.

LEBRON JAMES AND SAMSUNG

Lebron James
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When you’re the spokesman for tech giant Samsung, you’d better be careful what you tweet from the phone you’re being paid to promote. LeBron James was touting the new Galaxy smartphone in 2014 when he was a star member of the Miami Heat. When James tweeted on March 12 that his phone had just erased everything, it was pretty obvious what he was using. Though embarrassing, James deleted the tweet and shrugged it off. He continued to endorse Samsung products until 2017.

TEYANA TAYLOR AND ADIDAS

Teyana Taylor
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Don’t mess with Rihanna because the company you endorse is going to take her side. Singer Teyana Taylor found that out in 2013 when she was a spokeswoman for Adidas. A spat with then-bestie Rihanna quickly escalated online, and Taylor posted graphic police photos of Rihanna’s bruised face (allegedly caused by her boyfriend of the time, Chris Brown). Adidas, not wanting the bad publicity, dropped Taylor as a spokesperson shortly thereafter. This story has a happy ending, though; by 2016, the two women were BFFs again and Taylor tweeted about it.

OPRAH WINFREY AND MICROSOFT

Oprah Winfrey
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What could possibly go wrong when one of the world’s most beloved celebrities endorses your product? Microsoft Surface tablet earned a coveted place in Oprah’s Favorite Things in 2012. But when she actually used it, the technology didn’t lie. She tweeted “Gotta say love that SURFACE!” Too bad she used an Apple product to do so. The tweet contained a tag that read “via Twitter for iPad.” In the long run, the blunder didn’t seem to cause lasting damage to the popularity of either Microsoft or Winfrey. The Surface continues to be a big seller for Microsoft, and Oprah’s name has been floated as a 2020 Democratic presidential candidate.

ALEC BALDWIN AND WEGMANS

Alec Baldwin
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Actor and sometimes-talk show host Alec Baldwin is known for having a short temper, and in 2011 it was on full display during a flight. Baldwin was engrossed in a game of Words With Friends and wouldn’t turn off his phone for takeoff. After being ejected from the flight, he took to Twitter to rant. But if venting made Baldwin feel better, it also embarrassed the Wegmans supermarket chain, which Baldwin was endorsing at the time. They dropped him shortly thereafter.

RIHANNA AND NIVEA

Rihanna
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Rihanna got her revenge on Nivea when they dropped her as a spokesmodel in 2012. When Stefan Heidenreich took over as Nivea CEO, he decided the company’s image did not mesh with Rihanna’s sexy popstar lifestyle. Rihanna responded by tweeting a picture of Heidenreich with the caption “No caption necessary.” Nivea and the singer have both moved on, and Rihanna remains one of the most powerful celebs when it comes to commercial endorsements.

GILBERT GOTTFRIED AND AFLAC

Gilbert Gottfried
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The voice of the Aflac Insurance duck was the role Gilbert Gottfried was born to play, but he blew it with some tasteless jokes about the 2011 tsunami in Japan. The company, which at the time did most of its business in Japan, quickly fired Gottfried. The actor hasn’t had a major endorsement deal since, but continues to appear in film and television.

WILL.I.AM AND I.AM.CLOTHING

Will.I.am
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Black Eyed Peas singer and producer Will.I.Am. signed a six-year deal in 2010 to create and promote his own fashion line, I.Am.Clothing. But after 2012, he stopped tweeting promotions and later was sued for breach of contract. The fashion label quickly went bankrupt, and the pop star now limits his clothing sales to T-shirts on his website.

DAVID BECKHAM AND MOTOROLA

David Beckham
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After taking the rest of the soccer world by storm, David Beckham crossed the Atlantic to the U.S., where he joined the Los Angeles Galaxy in 2008 and quickly began amassing endorsement deals. One of those deals was for Motorola phones, so when a photographer caught him in 2009 sitting with an iPhone, the pics went viral. Beckham later said he was holding the iPhone for a friend. Motorola didn’t seem too upset; they retained Beckham as a spokesman for three more years.

KENDRA WILKINSON AND OLIVE GARDEN

Kendra Wilkinson
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Remember MySpace? The Playboy model and one-time Hugh Hefner girlfriend took it upon herself to endorse Olive Garden in 2008, praising the restaurant chain on her MySpace page. Olive Garden didn’t especially want an adult personality associated with their product, and certainly didn’t pay her for it, although they stopped short of asking her to stop. Instead, they chose to keep mum and waited for the kerfuffle to blow over. Wilkinson’s career since has been mostly in obscure reality TV shows.

Meet the Writer

Fred Topel has been an entertainment journalist since 1999, after he graduated film school at Ithaca College. After freelancing for a local paper, Fred became a full time entertainment journalist and has written for About.com, E Online, Hollywood.con, Syfy, Crave Online, Slashfilm, Rotten Tomatoes, Monsters & Critics, We Live Entertainment and many others.

There’s more to Fred than movies and TV though so he came to Cheapism to write about business, pets and other ways to save you money. Fred has three cats at home and volunteers at a shelter. Before journalism he worked as a movie theater usher and projectionist, so make sure to check out his reports on the best theaters to visit around the country.