Taylor Swift has been unlucky in love and now she’s making her riskiest bet yet. Her budding romance with Robert F. Kennedy Jr.’s son, Conor Kennedy is gaining steam, despite all the strife and dysfunction ripping through the Kennedy clan.

The Kennedy men have horrible reputations for the way they treat their wives and girlfriends, going back to family patriarch Joseph P. Kennedy, whose wife, elegant Rose Kennedy, bore a U.S. President, two U.S. Senators among nine children.

The Kennedys: A Legacy of Sex Scandals

Money, power and sex have not served the Kennedy clan well over the generations. Here are a sampling of scandals.

John F. Kennedy: The sexual escapades of the nation’s 35 present are legendary. The include flings with Marilyn Monroe and gangster moll Judith Exner Campbell. Kennedy was assassinated on Nov. 22, 1963.

Robert F. Kennedy: Also noted for legendary philandering, he had an affair with Monroe as well. He was secretly seeing her at the time of her death in Aug. 1962. Some speculate she committed suicide after Bobby broke up with her. He was shot and killed in 1968 while campaigning for president.

Edward M. Kennedy: Drove off a bridge at Chappaquddick after a raucous party, killing his passenger Mary Jo Kopechne. Kennedy saved himself, fled the scene and didn’t report the accident until after it was discovered the next day. Kopechne was found in the car without underpants. His wife, Joan Bennett Kennedy, became a raging alcoholic.

Kerry Kennedy:Daughter of Robert Kennedy, she was caught in a love affair with a married man in 2002, wrecking her marriage to New York Attorney General Andrew Cuomo and derailing his run for governor. She was recently arrested for driving under the influence of drugs.

Michael Kennedy: The son of Robert Kennedy was married to Victoria Gifford, the daughter of sports legend Frank Gifford, with three children, when he was caught in an affair with the family babysitter. He started having sex with her when she was 14. He died in a family skiing accident in Dec. 1997.

Robert F. Kennedy Jr.: He’d been married for 12 years to Emily Ruth Black when he started an affair with Mary Richardson. He left Black after Mary became pregnant. He admitted in court papers to numerous affairs during his marriage to Richardson, which became a source of friction leading to their divorce in 2010.

Joe Kennedy:, The son of Robert Kennedy was able to convince the Pope to annul his marriage of 12 years to wife Sheila Rauch. He never told her. That allowed him to remarry and stay in the church. Rauch only found out years later when he remarried. Her two sons with him were disowned.

Joe, who made a fortune on illegal whiskey, movies and real estate, has flamboyant affairs with a bevy of movie stars, including actress Gloria Swanson. Joe’s philandering has marked every generation since, up to and including the most recent scandal, involving Conor’s mother.

Mary Richardson Kennedy, estranged wife of Robert Kennedy Jr. and mother to Conor and three other children, hanged herself in May amid a bitter divorce. Robert Jr. was flaunting his relationship with actress Cheryl Hines at the time.

The Kennedy clan coldly cut off Mary, when her marriage crumbled, even though they had been as close to her as family since she was 15. Her family is so bitter at the Kennedys they tried to prevent Mary from being buried in a Kennedy family plot in Massachusetts.

Swift’s young psyche has already been roughed up by relationships with John Mayer, Joe Jonas and actor Jake Gyllenhaal. Getting involved with a Kennedy is like asking to be abused, but she’s clearly enamored by the Kennedy mystique.

The country singer was spotted in Nashville this week with Conor, 18, in tow. She reportedly introduced him to her parents as her boyfriend. The two have been dating since right after Mary’s death. She met the Kennedy family at their Cape Cod redoubt, and Ethel Kennedy praised their union.

She described meeting the 84-year-old matriarch as “the only time in my life I have ever been starstruck,” according to a Vogue interview.

But whether she can escape the Kennedy curse that has destroyed so many other Kennedy girlfriends and spouses remains to be seen. See the list above.