You Can Choose a Cabinet, But Not Your Family
Being president comes with enough public pressure without having a relative who turns every family gathering into a potential headline. Long before social media made every embarrassing moment permanent, presidential families had their share of dramatic, unconventional, and occasionally scandalous characters. These 20 relatives gave their presidential family members plenty of reasons to wish they could quietly change the subject.
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1. Billy Carter, Jimmy Carter’s Brother
Jimmy Carter’s younger brother Billy garnered fame through outspoken interviews and his own drink brand. Billy’s celebrity status would have been enough to create problems, but he also got the U.S. involved in Billygate when he started working with Libya. The president had no choice but to endure every scandal his brother caused on his own.
2. Elliott Roosevelt, Theodore Roosevelt’s Troubled Brother
Theodore Roosevelt’s younger brother Elliott Roosevelt was quite popular in social circles. Behind closed doors, however, Elliott was another story. His drinking, public outbursts, and affair with a family employee created a scandal that Theodore tried hard to contain.
B.J. Falk (1853-1925) on Wikimedia
3. Alice Roosevelt, Theodore Roosevelt’s Wild Daughter
Teddy Roosevelt once said he could take his sons out behind the sled and no one would notice, but you couldn’t keep Mrs. Roosevelt away from Alice. She was a vocal, bizarre child who refused to act like a proper presidential daughter. Rumor has it she carried around a snake named Emily Spinach.
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4. Eleanor Roosevelt, Theodore Roosevelt’s Niece
Eleanor wasn’t technically embarrassing, but her personality definitely didn’t fit in with her presidential relatives. She was the daughter of Theodore’s troubled younger brother Elliott and later became one of the most famous first ladies in American history. The family connections became even more unusual when Eleanor married her distant cousin Franklin Roosevelt.
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5. Sara Roosevelt, Franklin Roosevelt’s Overbearing Mother
As Franklin Roosevelt’s mother, Sara Roosevelt had many opinions on her son’s life and choices. When Franklin decided to marry Eleanor Roosevelt, she completely disapproved of the marriage. Franklin’s mother followed him around, giving his new wife a hard time until the day she passed away.
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6. Grover Cleveland’s Embarrassing Brother
President Grover Cleveland’s younger brother Richard Cecil Cleveland had a much more difficult relationship with public respectability. Known for his drinking and personal problems, Richard caused concern within the family and became another source of unwanted attention for the future president. Grover Cleveland spent much of his career dealing with his own scandals, so he was used to it.
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7. Mary Todd Lincoln’s Expensive Shopping
Mrs. Lincoln developed a reputation for extravagant spending on clothing and other goods during her husband’s term in office. People were seriously concerned about her spending habits during the Civil War. Apparently, budgeting for the White House was easier than keeping up with Mary Lincoln.
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8. John Todd Stuart, Lincoln’s Ambitious Brother-in-Law
Lincoln’s wife had relatives who were more than happy to meddle in his political and professional affairs. John Todd Stuart was Mary Lincoln’s cousin and former partner of Lincoln. As you can imagine, dealing with politics, business, and family all at once can get messy.
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9. Rachel Jackson’s Infamous Marriage Controversy
Andrew Jackson’s wife became extremely embattled by public scrutiny during their time in the public eye. Because Jackson’s wife Rachel’s divorce wasn’t finalized when she married Jackson, opponents accused them of indecent behavior. Andrew never got over the public attacks against his wife.
John Chester Buttre (1821–1893) on Wikimedia
10. Emily Donelson and the Petticoat Affair
Andrew Jackson’s niece Emily Donelson filled the role of White House hostess when his wife Rachel passed away. She became socially pressured during the Petticoat Affair scandal when she had to decide whom she would and wouldn’t accept socially. Imagine trying to manage a presidential household while everyone argues about who is invited to dinner.
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11. Randolph Jefferson, Thomas Jefferson’s Party-Loving Brother
Thomas Jefferson’s younger brother Randolph was described as much lighter in nature than his brother. Stories tell of Randolph visiting Jefferson at Monticello during evenings to play the fiddle and dance. For a president famous for serious intellectual pursuits, Randolph was the relative who seemed determined to keep things lively.
12. John Wayles, Thomas Jefferson’s Complicated Father-in-Law
Thomas Jefferson’s father-in-law, John Wayles, had children with multiple women during his lifetime. Some of these children were born into slavery, resulting in connections that Jefferson would later have to explain. The Jefferson family tree had enough branches to keep historians busy for generations.
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13. John Adams and His Unconventional Son Charles
Parents of presidential children know that sometimes children don’t live up to their potential. John Adams Sr. worried about the drinking and debt that plagued his son Charles. Even presidential families have difficult children.
14. Thomas Boylston Adams and His Unusual Politics
John Adams’ younger son Thomas Boylston Adams never reached the political heights of his father or older brother John Quincy. He spent much of his life moving between jobs, business ventures, and diplomatic work. Compared with the famously ambitious Adams family, his uncertain career path made him the less predictable branch of the dynasty.
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15. John Quincy Adams and His Unhappy Son George
John Quincy Adams’ eldest son, George Washington Adams, struggled with personal problems despite coming from one of America’s most prominent political families. He briefly pursued a political career but never reached the heights of his father or younger brother Charles Francis Adams. His troubled life and early passing became a sad chapter in the Adams family history.
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16. George Washington Parke Custis, Washington’s Difficult Stepson
George Washington took in his wife Martha’s children as his own, and his step-grandchildren followed suit. But once he passed, his step-grandson G.W.P. Custis took his connection to Washington to another level. He built Arlington mansion on land Washington left him and spent his life dramatizing his relationship to his stepfather.
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17. Martha Washington’s Grandchildren and the Family Drama
Martha Washington didn’t have children of her own but raised two of her own kids and four grandchildren. Life got hectic once the kids grew up and started having marital problems and drama of their own. George Washington may have been able to run a country, but nobody can control their grandchildren.
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18. Henry Lee III, Robert E. Lee’s Father and Washington’s Friend
American Revolutionary War hero General Henry Lee was a close friend and supporter of George Washington. Little known is that Washington’s future military opponent, Robert E. Lee, was Henry Lee’s son. Henry Lee later faced serious financial and legal troubles, but his friendship with Washington remained an important part of his legacy.
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19. John Payne Todd, Dolley Madison’s Chaotic Son
James Madison’s stepson John Payne Todd became notorious for debts and financial trouble. His behavior repeatedly caused headaches for Dolley Madison and drained family resources. Being the president’s stepson apparently didn’t make him any more interested in acting responsibly.
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20. William B. Randolph, Jefferson’s Scandalous Relative
Jefferson certainly had his fair share of political drama during his lifetime, but his in-laws were something else. The Randolph family was connected to everything from financial struggles and political scandals to family feuds. Jefferson may have been one of America’s greatest writers, but even he couldn’t edit his relatives out of the family story.
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