Joseph Lieberman was a Democrat who somehow belonged to both parties without fully fitting in with either. This is another way of saying that Lieberman’s true party was the Inside Party. To the extent that Republicans and Democrats have to answer to outsiders who want to change Washington, the Connecticut senator couldn’t be entirely at home on either team.

Ironically, Lieberman won national office in the first place because change-minded conservatives wanted to purge one of the last fossils of the GOP’s old “Eastern establishment.” Sen. Lowell Weicker was a Rockefeller Republican who irked the likes of William F. Buckley Jr. so much that Buckley—a Connecticut resident—endorsed his Democratic challenger in 1988. The state went Republican in that year’s presidential election: George H.W. Bush beat Michael Dukakis by more than 5 points. Lieberman, the Democratic challenger, beat Weicker by less than a single point in the Senate race.

Conservatives made the difference, but they paid a price. Connecticut has never again elected a Republican to the United States Senate. And the state—which voted for Ronald Reagan twice in the 1980s and even for Gerald Ford in 1976—has been won by the Democrat in every presidential election of the last 32 years. Rockefeller Republicans and conservative Republicans together could win federal elections in the state. But conservatives preferred a Democrat like Lieberman to a Republican like Weicker, and Rockefeller Republicans likewise came to prefer Democrats to any halfway conservative Republican.

Lieberman’s election was a disaster for conservatives in another way. The newly minted senator helped to accelerate the rise of the “New Democrats,” who presented themselves as more market-oriented than the big-government Democrats of old and less culturally radical than the left wing of the party. Bill Clinton and Al Gore were among the champions of this new movement, and the Clinton-Gore ticket would win both presidential elections of the 1990s. 

But from the start, the New Democrats were a fraud. In his first two years in office, while his party controlled Congress, President Clinton pursued left-wing policies on every front, from the FACE Act, which restricted the free speech and assembly rights of pro-life protesters, to gun control, gays in the military, and socialized medicine (“Hillarycare”). Lieberman was as socially liberal as Clinton, and later in the decade he even voted against a ban on partial-birth abortion. Yet he maintained an appearance of moderation by substituting the personal for the political: He voted radically, but he was serious about his Jewish faith and was outspokenly critical of violent video games and Clinton’s affair with Monica Lewinsky—though that didn’t stop Lieberman from voting against Clinton’s removal from office after he was impeached for lying under oath about the tryst. 

Lieberman demonstrated how character can disguise morally radical politics. He was a kind of whitewash, and that won him a spot on the Democratic presidential ticket in 2000. Vice President Al Gore didn’t need Lieberman as his running mate to provide policy experience or factional balance—they were both New Democrats—and the Connecticut senator wasn’t going to win Gore any state he couldn’t already count on. What Lieberman did was to lend his good character to absolve the vice president from association with Clinton’s sins. 

If New Democrats like Lieberman were not so different from the earlier McGovernite left where abortion and other cultural issues were concerned, however, they were indeed a break with the progressive tradition when it came to foreign policy and neoliberal economics. Lieberman, like his close Republican friend John McCain, was one of the most consistently bellicose figures in American politics. He was an early supporter of the Iraq War—and a late one, too, which cost him his party’s nomination for the Senate in 2006. But he again used Republicans to win a general election that he would otherwise have lost. 

That November, the Republican nominee for Senate received less than 10 percent of the vote—and while Connecticut was very much a blue state by then, it wasn’t so blue that a Republican could expect to draw only single-digit support. The Republican vote simply went to Lieberman instead of the GOP candidate, and enough of the Democratic vote did so as well that Lieberman, running as an independent, beat the antiwar Democratic nominee. 

America as a whole turned against the Iraq War in that election, causing Republicans to lose both the House and the Senate. But Lieberman secured re-election with plurality support in a three-way race by representing the establishment positions within both parties—the hawkishness of the Bush-era GOP and the social liberalism of Democrats then and now.

He continued to vote and caucus with the Democrats, but Lieberman increasingly exploited his Inside Party prestige with Republicans as well. He endorsed John McCain for president and spoke at the 2008 Republican National Convention. McCain seriously contemplated making Lieberman his running mate and was only dissuaded by the unavoidable fact that social conservatives in the GOP would never countenance such a thing. But if the choice had come down solely to Inside Party preferences, Lieberman would have been the pick. There was no other politician in America closer to McCain’s priorities. They were warhawks of a feather.

Lieberman retrospectively recognized that voters wouldn’t have bought what he and McCain wanted to sell. He joked that if he’d been selected by McCain he’d have had “the opportunity to take a unique place in history to have run for vice president on two different party tickets—and to have lost twice.” He was glad that “God saved me from that—or the Republican delegates saved me from that.”

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Yet up to his death on Wednesday, Lieberman still dreamed of making the Inside Party a force that could win elections. He became the founding chairman of “No Labels,” a project aspiring to field a centrist presidential candidate without a traditional party apparatus. Democrats, especially this year, perceive the initiative as a threat, given the conflicts within Joe Biden’s coalition over Israel and the risk that No Labels would split socially liberal voters with the Democrats while leaving social conservatives united within the GOP.

He will be remembered for being the first Jew on a major party presidential ticket. But he’s also significant as an archetype of his time. No politician better embodied the overlap between the Clinton and George W. Bush eras. Military adventurism, crony capitalism, and “character” as a quality that could spellbind social conservatives without inconveniencing social liberals—this was the Lieberman formula, and it’s still employed today, not least by those ex-conservatives who invoke “character” as their justification for siding with the party of the cultural left over the party of Donald Trump.

Lieberman was not a moderate. From war to abortion, his views were extreme. Those who only imagine a political spectrum with moderates in the middle and maniacs at the ends are wrong: Sometimes the middle is precisely where the culture of death is strongest. The senator was a man of good character but bad politics, and only voters more committed to the left and the right prevented him from doing greater harm in higher office.