Top 10 Second-Generation Political Screw-ups—Including Jesse Jackson Jr.

Jesse Jackson Jr. joins a long list of political scions who landed cushy jobs before losing them.

Former Rep. Jesse Jackson Jr. enters U.S. District Court in Washington, DC, Feb. 20, 2013. Jackson and his wife, Sandi Jackson, are expected to plead guilty to federal charges after being accused of spending more than $750,000 in campaign funds to purchase luxury items, memorabilia and other goods.

Former Illinois Democratic Rep. Jesse Jackson Jr. pleaded guilty to felony charges this week, admitting to violating a slew of laws by buying luxury items with political funds.

While most politicians caught up in scandals have humble beginnings, Jackson does join a sizeable list of second-generation politicians who became embroiled in scandal.

Jackson's plea deal, which includes jail time, comes a few months after he was re-elected in a heavily Democratic Chicago district, despite spending no time campaigning.

[RELATED: Jackson Jr. Resigns From Congress]

Most members of American political families are savvy enough to avoid embarrassing public spectacles, but a few seem to have assumed their political power grants them carte blanche to misbehave.

Below are nine politicians who—along with Jackson—have stumbled following a previous generation's footsteps.

Former Detroit Mayor Kwame Kilpatrick appears in Wayne County Circuit Court for his sentencing in Detroit, Mich., Oct. 28, 2008. Kilpatrick will spend 4 months in jail as part of a plea deal he accepted back in September in which he plead guilty to two felonies and no contest to a felony assault charge. (Bill Pugliano/Getty Images)

Kwame Kilpatrick: Kilpatrick served as mayor of Detroit from 2002 to 2008. His mother, Carolyn Cheeks Kilpatrick, was a congresswoman from 1997 to 2011. The mayor's downfall began in 2008 after he engaged in an affair with a subordinate—and sent her x-rated text messages using city phones. His mother memorably defended her son, telling supporters at a campaign rally, "don't let nobody talk about ya'lls boy, too many people have died!" After spending time in the slammer for the texting scandal, Kilpatrick's legal problems have continued with parole violations and an ongoing corruption prosecution.

Patrick J. Kennedy leaves his home May 5, 2006 on Capitol Hill in Washington, DC. During a press conference later in the day, Kennedy acknowledged his addiction and announced plans to seek treatment at Mayo Clinic. He also said he does not remember driving his vehicle into a security barrier near the Capitol. (Win McNamee/Getty Images)

Patrick Kennedy: Kennedy represented Rhode Island in Congress from 1995 to 2011. His father was Sen. Ted Kennedy. In 2006 Kennedy was apprehended by police after crashing his car into a roadblock near the Capitol at 2:45 a.m. He told officers that he was arriving for a vote, but later blamed the sleeping pill Ambien for his confusion. Not long after, Kennedy pleaded guilty to driving under the influence of prescription drugs and checked himself into rehab.

Edward Kennedy addresses the Democratic National Convention in Denver, Aug. 25, 2008. (PAUL J. RICHARDS/AFP/Getty Images)

Ted Kennedy: The longtime Massachusetts senator is somewhat of a sacred cow in American politics. His 1962 to 2009 tenure in the Senate was punctuated by the 1969 death of Mary Jo Kopechne. After a party on Massachusetts's Chappaquiddick Island, Kennedy drove his Oldsmobile off a bridge, then left the scene as Kopechne died. He was charged with leaving the scene of an accident, but denied that he was drunk at the time of the accident. Kennedy was the son of Boston powerbroker Joseph Kennedy, who served as Ambassador to the United Kingdom and who helped engineer the political rise of his sons, including President John F. Kennedy.

Former Sen. Chris Dodd (D-CT) speaks during the wake for R. Sargent Shriver at Holy Trinity Catholic Church in Washington, DC, Jan. 21, 2011. (Alex Brandon-Pool/Getty Images)

Chris Dodd: A longtime drinking buddy of Sen. Kennedy, Chris Dodd—a Democratic senator from Connecticut from 1981 to 2011—was accused of shenanigans of his own. In 2003, Dodd received mortgages from Countrywide at below-market rates allegedly as a special favor given because of his position on the Senate Banking Committee. He currently is the chairman and CEO of the Motion Picture Association of America. Dodd's father, Thomas J. Dodd, was a senator from 1959 to 1971.

Connie Mack speaks during a markup hearing before the U.S. House Budget Committee, March 15, 2010. (Alex Wong/Getty Images)

Cornelius Harvey McGillicuddy IV: Popularly known as "Connie Mack," the former Florida congressman—whose father was a senator—had a wild reputation in his youth. Highlights from these years include road rage incidents and bar fights, which featured prominently in 2012 attack ads. In November Mack lost his bid for the Senate seat represented by Democrat Bill Nelson.

President Franklin D. Roosevelt, with his son James, attend the state funeral for Sen. Thomas J. Walsh, March 6, 1933, who was to have been Attorney General in his cabinet. First lady Eleanor Roosevelt is seen at right. (AP Photo)

James Roosevelt: The son of former President Franklin D. Roosevelt, James Roosevelt was frequently in the news for the wrong reasons. In 1938 he resigned from a White House job as his father's assistant after being accused in news reports of improperly steering business toward his insurance company. Roosevelt was a California congressman from 1955 to 1965. In 1987 a political action group led by Roosevelt was investigated for frightening elderly people into paying for Social Security information available for free from the government.

A 1974 photo of Nelson A. Rockefeller, Vice President of the United States. (AP Photo)

Nelson Rockefeller: Although not a second-generation politician per se, the son of oil baron John D. Rockefeller Jr. entered politics with deep roots among the political class. Rockefeller served as governor of New York from 1959 to 1973 and as Vice President from 1974 to 1977. He died of a heart attack under peculiar circumstances in 1979. It was widely speculated that he died while having sex with a young woman who was not his wife.