Lieberman still caucuses with Democrats on the Hill, but conducting Senate business has become a delicate dance. The Democratic caucus meets every Tuesday. “If they’re discussing civil rights, gun control, he’ll be there. If it’s politics, he’ll leave,” says a high-level Capitol Hill staffer. The exclusive, bi-partisan chairman’s lunch, where committee chairs mingle, is held every other Wednesday. The Democratic Policy Committee lunch is on Thursdays. Lieberman usually skips that one altogether.
There’s also tension within the senator’s staff. “He’s well liked, he’s a good boss,” observes a Senate insider. “But some of them started working for a Democrat … and ended up with this.” One staffer, Melissa Winter, Lieberman’s trusted executive assistant and scheduler for ten years, and a member of his and his wife Hadassa’s inner circle, quit to join the Obama campaign.
The relationship between Lieberman and Obama goes back to 2005, when Lieberman found himself a mentor to the incoming Illinois senator. “The mentorship program was set up to reduce partisanship in the Senate,” Lieberman says, chuckling at the irony. His first impression of Barack Obama? Lieberman takes a long, lip-chewing pause. “Someone very smart and very likable.” For a couple of years, the relationship between the two men was said to be collegial. It is now quite obviously fraying. In the summer, an incident made rounds in the press wherein Obama supposedly buttonholed Lieberman on the floor and loomed over him in an intimidating way. A leak from Obama’s campaign suggested that the candidate confronted Lieberman on his insufficiently forceful rejection of Obama-as-Muslim rumors. One insider has another guess—that the conversation had to do with Obama’s unrequited support of Lieberman in the 2006 Connecticut Senate race. “Obama, once you get beneath his patina of aloofness, is a real guy. He talks very directly in private conversation. I wouldn’t be surprised if that was a conversation about that—‘Hey, bro, what’s the deal?’ ”
Lieberman’s strange road from the Democratic ticket to rumors of a place on the Republican one goes straight through Iraq. After he emerged from the 2000 presidential campaign with a cache of national name recognition and Democratic goodwill, it was only natural that Al Gore’s former running mate would ponder a presidential campaign of his own in 2004. Early polling put Lieberman among the front-runners, but there was one problem: the war. In 2002, Lieberman had called George Bush’s case for the invasion “powerful” and “eloquent.” And despite the fact that the war was now wildly unpopular, its pretext debunked, and its handling demonstrably terrible, Lieberman was still unapologetically cheerleading for it as the 2004 race began. The hawkishness boxed him in. “It’s just amazing when you look at where he was and what he squandered,” says Trippi. “He was in a position to be formidable, to be the guy you needed to get by. Instead, he positioned himself in a completely nonviable way. He just made himself untenable as a Democrat.” The campaign never gained traction, and staffers’ claims of “Joementum” became an instant media joke. Annoyed party elders, coalescing around Dean and Kerry, began hinting that Lieberman should bow out; he hung on instead, protracting the run far past its natural expiration date in his first open show of intra-party defiance. “I don’t want to say ‘ridiculous,’ ” recalls one veteran of the campaign, “but there were people who thought he should get out for his own dignity.”
The 2004 debacle was Lieberman’s first introduction to a new force, the netroots, a loose collection of leftist blogs including MoveOn.org and DailyKos. The way the senator sees it, those groups have been “taking the party in a direction that’s bad for America: take-no-prisoners, partisan attack politics.” Their influence, he says, has made the Democrats “litmus-testy” and “reflexively antiwar.”
But Lieberman hadn’t felt the full wrath of the blogs until his 2006 reelection bid. Online activists, including the coalition Trippi had built for Dean, were united behind Ned Lamont, a young businessman with no national-office experience but a vocal antiwar stance. To Lieberman, the blogs’ power in online fund-raising and event organizing—and the vitriol used to fuel it all—came as a shock. (The senator’s own Website, by contrast, crashed on the eve of the primary; his campaign blamed it on Lamont hackers until an FBI probe concluded that shoddy programming was the culprit.) On August 8, 2006, Lamont won the primary with 52 percent of the vote. “For the sake of our state, our country, and my party,” proclaimed Lieberman, “I cannot and will not let that result stand.” The inclusion of “party” in that sentence was jaw-dropping. There would be no concession in the name of unity: Lieberman had anointed himself the savior of the party, and he had to quit it to save it.