8 Most Embarrassing Presidential Family Members

Which president had the most embarrassing relative? From drunkards to doofuses, here is our list of the 8 worst offenders.

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Some presidents have had the good luck to be surrounded by relatives who helped build their public image. Other presidents aren’t so lucky. They continually wonder what their wife, child, brother, or in-law will next do to poach the news cycle and embarrass the administration.

Here are eight presidential family members who proved more of a liability than an asset.

John Payne Todd portrait
John Payne Todd, 1817 
(The Metropolitan Museum of Art)

1. John Payne Todd, Dolly Madison’s son from her first marriage, seemed to have been trouble from the start. John was often jailed for assault, disturbing the peace, and “shooting incidents.” He also had a serious gambling problem that landed him in debtor’s prison until his stepfather, James Madison, bailed him out.

President Madison gave John a chance to prove himself when he sent the young man with a diplomatic team to Russia in 1812. Diplomacy didn’t interest Todd. Women did. He ceased contact with his parents and spent his time with a countess. When the diplomatic team moved on to Germany, Todd decided to go to Paris instead. For the next three months, he spent a fortune at restaurants, casinos, theaters, and other places of Parisian entertainment.

He came home in 1815 after staying a year in Europe without doing anything except piling up $10,000 in debt.

Mary Lincoln (Library of Congress)

2. Mary Lincoln was a complex character. She undoubtedly helped promote Abraham’s career, prodding him to pursue higher offices and playing the hostess at party gatherings. But Mary also craved luxuries. In Springfield, Illinois, it might have been easy to control her spending, but when she and her husband arrived in Washington, things got out of hand. At a time when many Americans faced the hardships of life during the Civil War, she began an extensive redecoration of the White House, overspending her budget by 30%. She also blew a small fortune on her wardrobe and feared if her husband wasn’t re-elected, he’d have time to see her bills.

Insiders also claimed she stole from the White House. “Stealing was a sort of insanity in her,” said a lawyer who knew the family. She billed the government for materials she kept and even billed for a nonexistent employee so she could pocket the income.

Had Lincoln lived, she would have come under scrutiny for her lavish self-indulgence, but in the wake of the assassination, the country was ready to forgive her anything.

Alice roosevelt
Alice Roosevelt
(Library of Congress)

3. It was clear to America that Alice Roosevelt was certainly the daughter of her impetuous, noisy, and attention-seeking father, Theodore. After arriving in Washington, she soon earned a reputation for her rebellious spirit, flirtatious manner, reckless behavior, and talent for shocking people. She smoked cigarettes in public and was seen placing bets with a bookie. Attending receptions in gowns of her own personal color, “Alice Blue,” she would flirt with men while her garter snake wriggled on her blouse. Far from being a gracious, sweet-tempered first daughter, she was witty or, as some said, she had “quite a mouth on her.” At parties, she would say to newcomers, “If you haven’t anything good to say about someone, come and sit by me.” After repeatedly walking in to the Oval Office to give her dad political advice, Teddy told an advisor, “I can either run the country or I can attend to Alice, but I cannot possibly do both.”

Sam Houston Jonhson
Sam Houston Johnson (Wikimedia Commons)

4. Brother to President Lyndon Johnson, Sam Houston Johnson had a problem with alcohol. It became Lyndon’s problem because brother Sam, when intoxicated, spoke freely with anyone, particularly reporters. After leaking confidential information once too often, Johnson brought Sam into the White House, which he was unable to leave without the Secret Service following him and his conversations.

5. Donald Nixon, Richard’s brother, had dreams of becoming a fast-food king. In 1957, with his hamburger stand in trouble, Donald borrowed $200,000 to shore up his business. The lender was Howard Hughes, a major defense contractor. Richard Nixon had trouble convincing anyone that he, then vice-president, had not traded favors with Hughes for the loan. During the Watergate investigation, investigators learned that Donald had been a conduit for illegal campaign contributions to Richard. Yet Richard didn’t trust his brother and ordered the Secret Service to monitor Donald’s phone calls.

Jimmy Carter and his brother
Jimmy and Billy Carter (Wikimedia Commons)

6. Probably no brother caused a president more embarrassment than Billy Carter, who was nearly the complete opposite of his brother, Jimmy. Billy was a beer drinker of Olympian status who was always available to the press for a regrettable comment, or shameful behavior, like public urination at the Atlanta airport. His fame for beer consumption led a brewer to create Billy Beer. The brewer soon went bankrupt. To raise money, Billy opened his own diplomatic relations with Libya, hosting Libyan officials while they visited the U.S. Two years later, the Justice Department discovered the Billy was a paid lobbyist for the Muammar Gadaffi’s government and had accepted nearly a quarter million dollars for his services.

7. Roger Clinton Jr. is Bill Clinton’s half-brother but a complete embarrassment. When Bill was Arkansas’ governor in the 1980s, Roger served a year in prison for dealing cocaine. When Bill was president, Roger spent much of his time vainly striving to become a rock singer or movie star. (You may not remember him from such films as Pumpkinhead II: Blood WingsSpy Hard, and Bio-Dome.) As Bill neared the end of his presidency, Roger was also under FBI investigation for allegedly accepting money to get brother Bill to pardon six drug felons. Fortunately, Bill pardoned Roger’s drug conviction before he left office. Unfortunately, Roger was arrested for DUI one month later.

8. And then, there’s Neil Bush, son of one president, brother to another. He was accused of insider trading and selling his influence with presidential relatives. While brother George was president, he received $2 million in stock and $10,000 every time he attended a board meeting at Grace Semiconductor. Since Neil admitted he knew nothing about semiconductors, it was believed that Grace had hired him to influence his presidential relatives.But he is perhaps best remembered for his connection to Silverado Savings and Loan. After it collapsed in the late 1980s, Silverado was taken over by the government, which arranged a $1 billion bailout. Neil was eventually charged by the FDIC with negligence and conflict of interest and required to pay a $50,000 fine. He was also banned from the banking industry.

Featured image: Alice Roosevelt Longworth, daughter of Theodore Roosevelt, launching the USS Theodore Roosevelt on October 3, 1959. (U.S. Navy)

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  1. It looks like Donald Trump Jr. and Jared (Trump’s son-in-law) may make the numbers 1 and 2 spots in the near future–if they aren’t already there.

  2. The relatives of former presidents were certainly embarrassing but not nearly as embarrassing as our current pres and his obnoxious family. He’s over there kissing up to Putin , a vile despot who who is trying to destroy democracy all over the world. Trump even denied the credibility of our own intelligence agencies while he was on foreign soil. The great deal maker didn’t have the guts to stand up to Putin. Instead he said “it’s an honor to meet you.” Whaaaat? The stuff that he says and does should have landed him in prison, not our sacred White House. I still cannot believe he is the president. No wonder he’s sucking up to Putin. Putin’ s meddling probably got him elected. I’m just waiting for the truth bomb to explode. Then we’ll know the whole story. And the truth will come out!

  3. I like Bob’s short, succinct comments on each person. We can only make decisions for ourselves, not others, especially not family members. It all makes for interesting lives.

  4. John Pain Todd is more like it, and the first paragraph was the worst! Other than the interest in women and living the good life for awhile in Paris, this guy was indeed bad news. $10,000 of debt would be equivalent $148,000 now!

    Mary Lincoln was indeed complex, but also a tragic figure having only one of her four son’s outlive her, not to mention being next to Lincoln at the time of his assassination. Her extravagances at the time were out of control and she was quite cunning as well.

    If she had tendencies toward mental illness, the stress and sorrow almost put her over the edge. I certainly believe she had depression, and possibly have been bi-polar. Today, these would have been diagnosed and treated with therapy in addition to adjusted medications both pharmaceutical and hopefully natural treatments.

    As far as Alice Roosevelt goes, I KNOW I would have gotten a kick out of her! I like the idea of being of Alice’s husband and being supported in a lifestyle to which I’d become accustomed to, until the divorce of course.

    Sam Johnson apparently needed to be kept on a pretty short leash. Leaking confidential information while intoxicated. It seems the Secret Service did a good job keeping him in line.

    With Donald Nixon we have the ’50s and the ’70s intertwined with each other yet again, don’t we? What is it with those two? 1957/1972. Nixon & scandal, a fraudulent Hughes biography by Clifford Irving, Chuck Berry, Elvis back on the charts with hit songs. How often has THAT ever happened?!

    Moving to a completely different section of the ’70s, we have Billy Carter; best known for for that Atlanta airport incident and Billy Beer. It wasn’t good, but 40 years later we have never-ending daily drama and chaos by the President himself that makes that seem almost charming.


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