Showdown of the Scions? Chelsea Clinton and Caroline Kennedy Could Vie for New York Senate Seat

Many Democrats expect Sen. Kirsten Gillibrand (D., N.Y.) to mount a run for president in 2020. If she does, and ends up vacating her seat in the Senate, the race to replace her could feature a showdown between political scions Chelsea Clinton and Carolina Kennedy, according to the New York Daily News, which (dubiously) describes the pair as “the two biggest names in the Democratic Party.”

A prospect of a political showdown between the two former first daughters could be more than just fantasy. Democratic insiders have previously suggested that Chelsea is being groomed to run for Congress in 2018, which could provide a launching pad for a Senate campaign.

Chelsea’s increasingly saucy tweets have fueled speculation that the Clinton heiress is preparing to enter the political arena. “What you’re witnessing is the beginning of Chelsea Clinton’s political career, a family source told the Daily News.

If Clinton and Kennedy are both interested in filling Gillibrand’s seat, they wouldn’t actually have to run against each other and win an election, but would have to prevail in the political jockeying behind the scene if Gillibrand decides to run in 2020. If that happen, her successor would be chosen by the governor.

Kennedy was actually the first choice of former Gov. David Paterson to fill the Senate seat vacated by Hillary Clinton in 2009, but was forced to withdraw, citing “personal reasons.” Critics complained that Kennedy was devoid of charisma, lacked political experience and, like most Kennedys, could be weighed down with embarrassing family baggage.

Kennedy was forced to settle for an appointment as President Obama’s ambassador to Japan, from which she recently return home. Kennedy recently told NBC’s Matt Lauer she was in the process of “looking around to figure out what I would do next.”

Chelsea has not been shy about her political ambitions, telling Sky News in 2015 she would “absolutely” consider running for office in the future.

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