Top 10 Most Embarrassing Presidential Family Members

The oldest daughter of Theodore Roosevelt, Alice was 17 years old when she moved into the White House, and like her father, she had a rebellious side to her. She smoked, gambled, partied, and even kept a pet snake. She also lived a controversial lifestyle – allegedly having an affair with an Idaho Senator, who was also believed to be the father of her daughter Paulina. Known as “Princess Alice,” she was loved by the press for her provocative wit and charm. However, President Roosevelt saw her as a handful. When he was asked how he could keep her in line, he supposedly responded, “I can be President of the United States, or I can control Alice. I cannot possibly do both.”

This son of Franklin Roosevelt didn’t mind exploiting his family’s name for personal gain. He wrote a slew of mystery novels starring his mother, Eleanor, and a 1973 memoir, which discussed his father’s adulterous affairs. During his service in World War II, he rose quickly to brigadier general, prompting critics to accuse him of receiving special treatment. However, of greater concern was his involvement in numerous scandals. These included allegedly being part of a deal in 1934 to sell planes to the Soviet Union, as well as a shady loan arrangement and accusations of corruption related to Elliott’s broadcasting businesses.
 

Unlike the Bush twins or his drug addicted daughter Noelle, Jeb never did anything to embarrass his brother and father while they were president. However, he managed to disappoint the entire Bush family with his failed presidential bid in 2016. While Jeb started out as the front-runner for the Republican nomination, he quickly found his poll numbers dwindling to the bottom when Donald Trump got in the race. Toward the end, his campaign became sadder and sadder, proving that the Bush legacy was dead. Well, he did his best… so please clap. 

Also known as “Omar,” this half-uncle of Barack Obama was arrested for drunk driving in 2011, and he was detained by authorities when they found out he was living in the U.S. illegally. The White House claimed that the President had never actually met his uncle, but then had to walk back the statement when it was discovered that the two had lived together while President Obama was attending Harvard Law School. Onyango Obama’s sister, Zeituni Onyango, was also a political liability when her illegal immigrant status became public shortly before the 2008 election.

A White House official once said: “you never wanted to hear their name come up in any context other than playing golf.” These two brothers-in-law to Bill Clinton wanted to use their ties to the president to cash in. Hugh and Tony tried to corner the hazelnut market in the republic of Georgia, a 118 million dollar deal that involved working with the Georgian president’s rival. To prevent an international incident, Bill Clinton and his National Security Advisor had to convince the two brothers to drop the deal. In 2001, Hugh received 400,000 dollars from a client for whom he sought a pardon, but he had to return the money because of the blowback.

This daughter of Ronald Reagan not only disagreed with her father’s conservative policies; she also accused her parents of being emotionally distant from her. Besides being an outspoken activist in the anti-nuclear movement, she published a novel in 1986 called “Homefront,” getting inspiration from her personal life. Patti’s 1992 tell-all autobiography, “The Way I See It,” cast her family in a negative light and went into detail about her mother’s prescription drug abuse. In 1994, she appeared nude on the cover of Playboy and again for More magazine in 2011. Luckily, Patti and her family eventually settled their differences before Ronald Reagan passed away in 2004.

Son of George H. W. Bush and brother of George W. Bush, Neil was always getting into trouble in one way or another. He was a member of the board of directors of the Silverado Savings and Loan, which received a 1.3 billion dollar bailout from taxpayers. For his actions, the Federal Deposit Insurance Corporation sued Neil and his partners for negligence. From divorce proceedings in 2003, it came to light that he had slept with prostitutes from Thailand and Hong Kong, though he denied they were sex workers because he didn't give them money. Whatever you say, Neil.

The younger half-brother of Bill Clinton, Roger had a fitting Secret Service code name during Bill’s time in office: “Headache.” Roger took advantage of his brother’s fame and borrowed a bit of the spotlight, getting small parts in movies throughout the ‘90s and trying to make a name for his band, Politics. In 2001, he received a pardon from his brother for a 1985 cocaine conviction after serving a year in prison, and got arrested one month later for drunk driving. He then tried to pay it forward by advocating the pardon of a drug-dealing friend from whom he received money for services. 

We go from one troublesome little brother to another with this sibling of Jimmy Carter. Despite being well educated, Billy played up his own brand of hillbilly shtick, which included taking a leak on an airport runway in the presence of dignitaries and reporters. After his brother was elected, Billy took advantage of his newfound celebrity by opening his own line of Billy Beer, but it went bust within a year. While his brother was president, he became a registered agent for the Libyan government and was given a 220,000-dollar loan, which resulted in a Senate investigation that the press referred to as Billygate.

Before we unveil our number one pick, here are a few honorable mentions.

Oscar Cleveland

Mary Todd Lincoln 

Donald Nixon

So many embarrassing Kennedys to choose from, whether it’s William Kennedy Smith who was accused of rape or Michael Kennedy who was accused of statutory rape. But we’re giving our top honor to Senator Ted Kennedy, whose drinking and womanizing were highlighted in a 1990 GQ profile, aptly titled “Ted Kennedy on the Rocks.” And who can forget the drunk driving incident at Chappaquiddick Island where he drove off a bridge and left a young woman to drown in his car? In 1980, Kennedy tried to put the tragedy in the past and made a run for president in an unsuccessful attempt to unseat Jimmy Carter. Even with his distinguished political career, that alone is more than enough reason for him to be #1 on our most embarrassing presidential family memberslist.

Do you agree with our list? Which presidential family member do you think was the most embarrassing? For more political top 10s published every day, be sure to subscribe to WatchMojo.com.