Almost a year to the day before the 2000 presidential election, Beltway insiders met at a comedy club in Washington, D.C., to roast one another at the annual “Funniest Celebrity in Washington Contest.” At the previous event, Kellyanne Conway, now counselor to President Donald Trump, had performed stand-up and sang an awkward a cappella version of a song, “I’ve Got the Pundit Blues,” while wrapped in a feather boa. At the 1999 gathering, Billy Bush, of Trump “hot mic” infamy, joked that a theoretical President Trump would clean up the federal budget since “he’s already managed to cover 90 percent of his head with only 3 percent of his hair.”
Joe Lieberman, then a Democratic senator for Connecticut, also joked about what a Trump presidency might look like. “The Donald is quite a ladies’ man,” Lieberman said. “He’s going to have, if elected, an all-female cabinet…. Secretary of Energy Carmen Electra, Secretary of Defense Xena the Warrior Princess.” The audience roared with laughter. Trump would “probably turn the White House into luxury high-rise co-ops,” Lieberman said, “but it would be very hard for any Jews to get in.”
Almost two decades later, Lieberman is reportedly Trump’s top pick to replace James Comey as FBI director. Some might find the news surprising, given Lieberman’s ties to the Democratic party. He was Al Gore’s running mate in the 2000 presidential election and ran as a Democratic presidential candidate early in the 2004 race.
But Lieberman has been shifting to the right for years. Jim Manley, a longtime Democratic strategist and a former senior communications adviser for former Senator Harry Reid, points to the impeachment proceedings of President Bill Clinton as a turning point for Lieberman and the Democrats. “He spent a lot of time moralizing about [Clinton’s] actions, which kind of ticked some people off,” he says.
That chasm widened under President George W. Bush, when Lieberman supported the Iraq War. Then in 2006, after entering the Connecticut senate primary race as a Democrat and losing, he switched affiliations to Independent so he could run in the general election. He won, thanks to Republican voters, who were dissatisfied with their own candidate.
The ordeal soured the Democrats on Lieberman, according to Scott McLean, a political science professor at Quinnipiac University and an observer of Connecticut and national politics. “There was no way he was ever going to get back in the good graces of the Democratic party,” he says. The election soured Lieberman on the Democrats, too. “They just sort of let him go down in flames in that primary,” McLean says. “He never forgot that.”
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