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Hunter Biden, the son of President Joe Biden whose plea deal on federal tax and gun charges was made public Tuesday, is by no means the first presidential relative whose personal troubles have brought unwelcome headlines and headaches for a White House.

The younger Biden will plead guilty to misdemeanor tax offenses in an agreement that also allows him to avoid full prosecution on a felony charge of illegally possessing a firearm as a drug user, as long as he abides by certain conditions. The deal closes a long-running Justice Department probe into Hunter Biden, long known to struggle with substance abuse.

Children of U.S. presidents, like Hunter Biden, have long been subjects of fascination and curiosity, with their every move under public scrutiny.

Former President Donald Trump’s son Donald Jr., for one, was in the news for meeting with Russian operatives offering damaging information on Hillary Clinton during the 2016 presidential campaign.

Sometimes the behavior is pure mischief, such as little Quentin Roosevelt (son of Teddy) running his toy wagon through a painting of a first lady. Or Alice Roosevelt, Quentin’s sister, who swore, showed up at parties with her pet snake and was so determined to smoke at the White House that she once called a news conference on its roof and lit a cigarette there.

“I can either run the country or I can attend to Alice, but I cannot possibly do both,” the president famously lamented.

Other misbehavior by presidential children has been more serious, and run afoul of the law.

Jenna and Barbara, the twin daughters of President George W. Bush, were each busted for underage drinking during a five-week span in 2001. Jenna Bush Hager, who now works as a television host for NBC, described during a conversation on “Today with Hoda & Jenna” how her father responded with regrets of his own as she tried to apologize.

“When I called my dad to say, ‘I’m really sorry’ … he said, ‘No, I’m sorry,’” Bush Hager said. “He said, ‘I’m sorry, I told you you can be normal, and you can’t. You can’t order margaritas.’” She added of her parents: “We embarrassed them, although they never said it, on the world stage.”

Both John Adams, the second U.S. president, and his son John Quincy Adams, the sixth, had children who suffered from alcoholism. George W. Bush, himself a future presidential child, was arrested for drunken driving in 1976 at the age of 30, and decided to give up alcohol a decade later.

For several presidents, the financial dealings of relatives have caused unpleasant publicity.

One notable example was Billy Carter, the beer-loving younger brother of President Jimmy Carter who was already known for making racist and anti-Semitic remarks when he registered as a paid agent of the Libyan government and accepted $220,000 from Tripoli that covered his bills and various expenses.

Calling the Libyans “the best friends I’ve got in the world right now,” Billy Carter’s actions came under scrutiny of the Senate Judiciary Committee, which unanimously voted to establish a panel to look into the first brother’s business dealings abroad. The committee at the time included a young Sen. Joe Biden, D-Del.

Richard Nixon once asked the CIA to put a “full cover” on his brother Donald, whose business connections the president blamed hurting him in elections, according to books written by former Nixon aides. Although the CIA declined, the Secret Service agreed to keep watch on Donald, who had ties to the billionaire Howard Hughes and once received a $205,000 loan from him.

Neil Bush, one of President George H.W. Bush’s six children, was an outside director at a failed savings and loan association that came under scrutiny of federal regulators in the 1990s. He did not face criminal charges but did agree to help settle a civil case brought by the Federal Deposit Insurance Corp. as one of a dozen defendants in a negligence suit.

Neil Bush had faced accusations of conflict of interest through his position at Silverado Banking, Savings and Loan Association in Denver, which he repeatedly denied. He asserted that he was unfairly targeted because he was a son of a president.

The brothers of former first lady Hillary Clinton — Tony and Hugh Rodham — were publicly rebuked by their brother-in-law’s administration for a planned business venture that would entail exporting hazelnuts from the republic of Georgia with assistance from a political rival of Eduard Shevardnadze, who was the country’s president at the time.

Though the Clinton White House distanced itself from those dealings, it didn’t hesitate to offer presidential help to other family members.

Shortly before leaving office in 2001, President Bill Clinton pardoned his half-brother, Roger, for a 1985 drug offense in which he conspired to distribute cocaine. The president credited the conviction for helping to turn Roger Clinton’s life around and told then-U.S. attorney Asa Hutchinson, the prosecutor in the case, that the episode probably saved his brother’s life.

“The prosecution was very tough on the family and then-Governor Clinton responded to it as a loving brother would,” Hutchinson, who is now running for the Republican presidential nomination, told the Associated Press at the time. “I haven’t followed Roger that closely, but I know he’s made an effort to change directions.”

Originally published by Federal Times, our sister publication.