The scion of one of America's most prominent political dynasties, he was almost kicked out of Harvard for getting drunk and running naked through the campus with some of his buddies.
Later, he descended into alcoholism, losing thousands of dollars in shady land-speculation schemes and was rejected by his father, who considered him morally deficient, "a Madman possessed of the Devil."
A Kennedy or a Rockefeller? A Gore or a Bush?
No, an Adams. Charles Adams, one of the sons of President John Adams, was the black sheep of his family, whose outrageous behavior and alcohol-fueled hijinks were a continual source of embarrassment to his parents and siblings.
Long before Al Gore III was arrested for marijuana possession and the Bush daughters were busted for underage drinking and a slew of Kennedys had made headlines for committing crimes, America's most important families were plagued by embarrassing relatives.
Of course, every family has a few bad apples, the source of hushed gossip behind closed doors. While political dynasties have always commanded attention, when one of their ranks stirs trouble, breaks the rules or falls down drunk, the incident becomes irresistible fodder. Famous black sheep are held to a different standard. Sometimes they can even do irreparable damage to the political fortunes of family members.
So far, the arrest of former Vice President Al Gore's son, Al Gore III, Wednesday morning for allegedly possessing marijuana and prescription drugs, doesn't seem to pose a threat to his father's potential political ambitions. The elder Gore has repeatedly claimed that he is not interested in running for president again. But his son's plight and his announcement that he is entering a rehabilitation program seem to be drawing sympathy from political pundits and observers.
Other families have not been as lucky, especially the Kennedy dynasty, several of whose members have seen their careers stunted due to their behavior. Most noteably Ted Kennedy's presidential ambitions were permanently thwarted in 1969 by the Chappaquidick scandal in which he drove a car off a bridge on Martha's Vineyard. His female companion drowned, and so did his highest political aspirations.
His son Patrick Kennedy, a congressman from Rhode Island, crashed his Ford Mustang into a barricade at Capitol Hill last year, claiming that he was disoriented from the prescription medications Ambien and Phenergan, although officers at the scene said that he smelled of alcohol. The younger Kennedy, who has acknowledged being treated for cocaine use as a teenager, later admitted himself into a drug rehab clinic in Minnesota. He had recently expressed interest in running for the Senate, but since the accident, Kennedy seems to have lowered his ambitions to simply getting re-elected.
And in the category of famous black sheep, it's hard to leave out William Kennedy Smith, Patrick's cousin. Both Patrick and his dad were hanging out with William at a bar in Palm Beach, Fla. in 1991, the night their relative allegedly raped a young woman. Kennedy Smith was later acquitted of all the charges against him.
Are political dynasties really more prone to having black sheep in their ranks?
"It's hard to tell, but it does seem that it crops up in some ways in almost every political family," said Noemie Emery, the author of "Great Expectations: The Troubled Lives of Political Families."
She explained that the pressures of being in the public eye can work both ways on the families of prominent politicians. "It seems to drive them into opposite directions -- either perfection or absolute disillusion," said Emery, noting that Al Gore III was already getting into trouble as a high-schooler when his father was the vice president in the late 1990s. "It certainly seems to fit a pattern that goes back to 1790 when John Adams had a son that drank himself to death. … Some feel that they can't live up to those expectations, and they pre-emptively give up at the beginning. I kind of feel that happened to David Kennedy, the son of Bobby, who died of a drug overdose in 1984."
Emery believes that it's easier to be a daughter than a son in such families. "Girls don't have that direct competition with the father. Fathers don't look at the baby girl in the cradle and say, 'You'll grow up to be president,' whereas Al Gore and John F. Kennedy's older brother, Joe, were appointed to the presidency from the cradle."
According to Emery, the day that Al Gore was born, his grandfather held a press conference announcing that he was going to become president, and his father planted a story on the front page of the local paper about Gore's birth.
One exception to the rule about boys was a member of the Roosevelt dynasty. "Teddy had a rambunctious daughter named Alice, a Paris Hilton before her time," said Allan J. Lichtman, a presidential historian who teaches at American University. "She wasn't doing anything illegal but pushing the envelope of what was acceptable in terms of drinking and partying."
Decades before the Bush twins were drinking underage and embarrassing their parents, President Roosevelt famously remarked about his daughter, "I can be president of the United States, or I can control Alice. I cannot possibly do both."
Lichtman can recite a long list of dynastic black sheep, claiming that the children of the powerful often suffer from the pressure to live up to success.
President William Henry Harrison had an embezzler and an alcoholic as sons. One of Franklin Roosevelt's five sons married five times and actually became a Republican, to the great embarrassment of his mother.
"It's a constant throughout American political history," said Lichtman. "It may have something to do with absentee fathers. Look at the kinds of personalities that go into politics -- they tend to be hard-driving and ambitious, and their kids are under a lot of pressure."
And of course the entire family is on the public stage. "Alice Roosevelt was no different than thousands of other women out there, but she was the daughter of the president, so it was on the front page," said Lichtman.
Knowing that their behavior is being watched by millions, why do so many children and relatives of political dynasties get into trouble?
Psychologists say that black sheep are rebelling against their family's values, whether they value religion or social respectability or public service. "If money is a family value, then the kid might become a ne'er-do-well," said Louis Wynne, the author of "Healing the Hurting Soul: A Survivor's Manual for the Black Sheep in Every Family."
"This is a phenomenon quite common across the board. I don't think the Bushes and the Gores are any different from my family or yours. But if you're a prominent family like the Kennedys and Chappaquiddick [happens], there is no way to sweep that under the rug."
It's impossible to know what's really going on inside someone else's family, and yet since the Gores have displayed such a commitment to public service, Wynne speculated that Al Gore III's behavior may be an act of rebellion. "He knew that it would break the rules and go against the family values."
Elizabeth Stone, the author of "Black Sheep: Kissing Cousins" argued that Al Gore III's behavior seems to be a direct contradiction of his father's "goody-goody" image.
"His son is something of a bad boy, always getting into scrapes, but with a vulnerable streak," she said. "American folklore, at least, always shows a begrudging admiration for the good-hearted bad boy. At the very least, the prodigal son can't make a comeback without something to make a comeback from. Remind you of anyone, say, a current president?"