© Getty Images

John Payne Todd (1792-1852) -

The stepson of President James Madison, John Payne Todd 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 bailed him out.

© Public Domain

John Payne Todd (1792-1852) -

James Madison (pictured) gave his stepson a chance to prove himself when he sent him with a diplomatic team to Russia in 1812. However, diplomacy didn't interest him. John ceased contact with his parents and went to Paris instead. There, he spent a fortune at restaurants, casinos, and theaters. He came home to the US in 1815 with a debt of US$10,000.

© Getty Images

Mary Todd Lincoln (1818-1882) -

Abraham Lincoln's wife, Mary, was a complex figure. While she helped promote his career, she also craved luxuries. In Springfield, Illinois, it might have been easy to control her spending, but when she arrived in Washington, things got out of hand. 

© Getty Images

Mary Todd Lincoln (1818-1882) -

At a time when many Americans faced the hardships of the Civil War, she began an extensive redecoration of the White House and spent a small fortune on her wardrobe. This was a source of much consternation.

© Getty Images

Alice Roosevelt Longworth (1884-1980) -

A controversy magnet, the oldest daughter of Theodore Roosevelt Alice was 17 years old when she moved into the White House.  

© Getty Images

Alice Roosevelt Longworth (1884-1980) -

Alice smoked, gambled, partied, and even kept a pet snake. Known as "Princess Alice,"  she was loved by the press for her provocative wit and charm.

© Getty Images

Elliott Roosevelt (1910-1990) -

The son of Franklin D. Roosevelt and Eleanor Roosevelt published a book about his attendance at several major Allied war conferences and a controversial exposé of his parents' private life, which discussed his father's adulterous affairs. He also wrote 22 mystery novels. 

© Getty Images

Elliott Roosevelt (1910-1990) -

During his service in World War II, he rose quickly to brigadier general, prompting critics to accuse him of receiving special treatment. He is pictured here with his father and Winston Churchill. 

© Getty Images

Sam Houston Johnson ( 1914-1978) -

Brother to President Lyndon B. Johnson, Sam was an alcoholic. One of the issues was that when he was intoxicated, he would speak freely with anyone, particularly reporters.

© Getty Images

Sam Houston Johnson ( 1914-1978) -

After leaking confidential information once too often, he was brought into the White House, which he was unable to leave without the Secret Service following him.

© Getty Images

Ted Kennedy (1932-2009) -

In 1969, Senator Ted Kennedy crashed off a small bridge on the tiny Massachusetts island of Chappaquiddick and landed in the water. With him was 28-year-old Mary Jo Kopechne, who was left in the car and drowned. The incident derailed his presidential ambitions for good.

© Getty Images

Ted Kennedy (1932-2009) -

Apart from the tragic Chappaquiddick incident, Ted was known for his drinking and womanizing ways, which were highlighted in a 1990 GQ profile, aptly titled "Ted Kennedy on the Rocks."

© Getty Images

Billy Carter (1937-1988) -

President Jimmy Carter's brother had a string of public embarrassments. His multiple incidents of public drunkenness became so famous that he launched his own brand of Billy Beer. 

© Getty Images

Billy Carter (1937-1988) -

Things took a serious turn in 1980 when Billy registered as a paid agent of the Libyan government, and accepted a US$220,000 payment from Tripoli. This triggered an investigation by the Senate Judiciary Committee, which included a young Senator Joe Biden.

© Getty Images

Patti Davis (1952-) -

Ronald Reagan's daughter Patti Davis spoke out publicly against her father's politics and even published a tell-all book. She was active in the anti-nuclear movement before her father was elected president, and continued her activism through his term. 

© Getty Images

Patti Davis (1952-) -

In the July 1994 issue of Playboy, Davis posed for the magazine with a full-frontal pictorial. The issue is considered to be one of the magazine's most controversial covers.

© Getty Images

Hugh (1950-) and Tony Rodham (1954-2019) -

Hillary Clinton's brothers, Hugh and Tony Rodham, were both accused of shady business dealings with the Georgian president's rival while their brother-in-law, Bill Clinton, was in office.

© Getty Images

Roger Clinton (1956-) -

Meanwhile, Roger Clinton, Bill's half-brother, had a string of drug-related incidents that earned him the Secret Service codename "headache."

© Getty Images

Neil Bush (1955-) -

During the presidency of his father,  George H. W. Bush, Neil voted to approve US$100 million in what were ultimately bad loans to two of his business partners. In voting for the loans, he failed to inform fellow board members at Silverado Savings & Loan that the loan applicants were his business partners. For his actions, the Federal Deposit Insurance Corporation sued Neil and his partners for negligence. 

© Getty Images

Neil Bush (1955-) -

From divorce proceedings in 2003, it came to light that Neil had slept with several sex workers in Thailand and Hong Kong. He said he didn't know they were sex workers, claiming they never asked for money and he didn't pay them.

© Getty Images

Omar Onyango Obama (1944-) -

Barack Obama's Kenyan half-uncle, Omar, was arrested for drunk driving in 2011. He was detained by authorities when they found out he was living in the US illegally.

© Getty Images

Zeituni Onyango (1952-2014) -

Omar's sister, Zeituni Onyango, was also a political liability when her illegal immigrant status became public shortly before the 2008 election. She became a legal resident in 2010.

© Getty Images

Jeb Bush (1953-) -

Although Jeb Bush didn't embarrass his brother and father while they were president, he did disappoint the Bush family with his failed presidential bid in 2016. 

© Getty Images

Jeb Bush (1953-) -

While Jeb started out as the front-runner for the Republican nomination, he quickly found his poll numbers declining when Donald Trump joined the race. 

© Getty Images

Donald Trump Jr. (1977-) -

President Donald Trump's son Don Jr. has earned his share of headlines for meeting with Russian operatives offering dirt on Hillary Clinton.

© Getty Images

Donald Trump Jr. (1977-) -

Don Jr. also pushed Trump's business overseas, with deals that may have benefited from his father’s position.

© Getty Images

Hunter Biden (1970-) -

In June 2024, President Joe Biden's son, Hunter, was convicted of three federal firearms-related felony charges after he had admitted to illegally owning a gun while a drug user in 2018. 

© Getty Images

Hunter Biden (1970-) -

Hunter is the first child of a sitting president to be the subject of a criminal trial. His trial is scheduled for September 2024. 

Sources: (BBC) (The Saturday Evening Post) (Fox News) 

© Getty Images