The Audacity of Hillary

Hillary Clinton might be the Dems' presidential front-runner, but the trip to the White House makes a stop in Obama Country. Can the hometown girl beat the state's favorite son on what's now his home turf?

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On the night of March 17, 1992, St. Patrick's Day, Bill and Hillary Clinton took the stage of the Palmer House Hilton ballroom, amid flags and colorful confetti, to celebrate Bill's campaign primary victory. Clinton got more than half of the statewide vote, beating out the former California governor Jerry Brown and U.S. senator Paul Tsongas, of Massachusetts, who had weeks earlier upset Clinton in the influential New Hampshire primary. Clinton's triumph here (and also in Michigan the same day) helped him rebound from that stinging New Hampshire loss and effectively sealed the presidential nomination for him. 

Returning to the Palmer House in early 2001 for a farewell appearance on one of the final days of his presidency, Clinton recalled that key win in the Illinois primary: "Ever since then, I have known that when the chips were down, Chicago and the state of Illinois would be there," he said, adding, "It's doubtful I could have been president without the support of Illinois and Chicago."

A large framed photograph of the Clintons onstage that primary night in 1992 hangs on a wall in the downtown law office belonging to attorney Kevin O'Keefe. The office is like a photo gallery devoted to the Clintons, "but this one's the best of all," O'Keefe says of the St. Patrick's Day shot. The picture is signed by Hillary Clinton: "To Kevin, with gratitude for all your support and friendship over the years and for all of the laughs along the way."

A close friend of Hillary's since they double-dated in college, O'Keefe later served in the Clinton White House and ran Bill Clinton's first presidential campaign here. Today, O'Keefe is leading Hillary's Illinois campaign, and with Obama in the race, he knows his task is harder. "I think if the primary were held today, Senator Obama would win," says O'Keefe. "He's from Illinois, he got 70 percent of the statewide vote in the Senate race, just about every elected official in the state is supporting him, and a lot of major donors and activists in the state know him and are supporting him—and they oughta be."

A dead ringer for Dick Cheney, O'Keefe sat in his office recently—on the same couches, he reminds me, where he sat discussing tactics with Bill and Hillary in the 1992 campaign—and explained how his candidate would challenge Obama in his home state: "Job one is fundraising—we have to raise more money here. Job two is to get her on the ballot, the petition drive. Job three is to select and slate a full field of delegates pledged to her and get them on the ballot." Any secret weapons to winning? "Yeah," he replies, "Bill and Hillary Clinton." 

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This year illinois Democrats think that the state can become a bigger influencer in the nomination process, now that state lawmakers have moved up the primary six weeks to February 5th, on what's being dubbed Super-Duper Tuesday, when 22 states are holding their primaries. The move in Illinois was part of an effort by Illinois Democratic leaders to boost Obama's prospects. Up for grabs are 185 Illinois delegates, but more important, a win here would reverberate, which is why O'Keefe and others are so eager to position Clinton's Illinois race as an "insurgent campaign." He points out that in 1988, when Illinois senator Paul Simon won the Illinois Democratic presidential primary, he trailed all three of his main rivals—Michael Dukakis, Al Gore, and Jesse Jackson; he hadn't won any of the early-state primaries; and his campaign was deep in debt. "That shows you the strength of an Illinois senator in Illinois in the presidential primary," says O'Keefe. "So, if we were to defeat Senator Obama in the Illinois primary, it would be a monumental upset."

In fact, the race here may be closer than it appears. Obama's huge lead in endorsements, for example, may not mean muscle in an actual election. U.S. senator Chris Dodd, also one of Clinton's 2008 presidential rivals, has racked up endorsements in his home state of Connecticut from every statewide official and legislative leader, plus the backing of 89 town committees. Yet, in every statewide poll, Dodd is far behind in the crowded Democratic pack, according to the Quinnipiac University Polling Institute, which is based in Connecticut.

Clinton supporters in Illinois refer to an independent poll taken in July that shows Obama holding only a slim four-point lead over Clinton in the state, 37 percent to 33 percent. In January, the same poll had Obama up by six. After her late start in the statewide money chase, Clinton's fundraising apparatus seems to have finally moved into full swing. And today, the Clinton camp is recruiting some of the state's best and brightest political operatives and fundraisers, including some old White House hands, plus, they say, a list of 5,000 potential volunteer foot soldiers.

Still, Clinton doesn't have an official campaign office here. O'Keefe says volunteers work out of their homes, and local campaign meetings are held in the business or law offices of various supporters. Compare that with Obama, whose national headquarters is downtown on Michigan Avenue, staffed by some 200 full-time workers. The Obama campaign also claims a list of more than 23,000 volunteers statewide.

Stacey Zolt Hara admits that Clinton's base of political support might be "a small group," compared with Obama's, but, she adds, "it's also a very passionate group, and it's definitely growing every day." In July, for example, Terrence Duffy, chairman of the CME Group—the newly merged Chicago exchanges—and a major Republican fundraiser twice appointed to federal posts by President Bush, endorsed Clinton and pledged to raise money for her.

Other Clinton campaign insiders claim that—despite what appears to be near across-the-board local support for Obama's presidential bid—a good number of political leaders, donors, and activists are privately saying that they'll actually vote for Clinton, not Obama. Without naming names, Pritzker says: "What we hear a lot is—‘Look, as you can imagine, I have to be with Senator Obama.' But most people believe that [Clinton] will become the nominee for president, and most people believe that, actually, she'll win the presidency. So there's an awful lot of people who are finding it easy to stay publicly with Barack Obama in the primary, knowing that they'll be supporting her in the general [election]."

Ben LaBolt, an Obama campaign spokesman, scoffs at that suggestion: "Support in this state has been very unified behind Senator Obama," he says, "and we're not taking anything for granted. Senator Obama is also, by the way, competing in New York and has secured endorsements and found significant support there."

State representative Jack Franks is one Obamamaniac who's had a recent political change of heart. Franks once served on Obama's presidential exploratory committee and encouraged his friend to run, telling his district's local paper: "He's the right guy at the right time." But now Franks says his timing wasn't right, choosing Obama even before evaluating the rest of the presidential field. Franks started having second thoughts about Obama after watching his performances in the first couple of debates. "I thought that Hillary was by far the better candidate and the only one ready to lead from day one," he recalls. "But when my kids say, ‘Then why are you with Barack?' I couldn't give them a good answer—except friendship."

After his defection became public, Franks says, he got an earful from more than a few of his constituents and other outraged local Democrats, not to mention an angry phone call from one Obama staffer. "They were unhappy—they were aggressive in how they responded," he says, of the Obama team. "But I don't blame them." Franks says Obama hasn't spoken with him since he jumped ship. "I don't think Barack is vindictive," he says. "I think there are some people in his campaign organization who'd like to be, but I don't think [Barack] operates that way." Franks frowns, and then adds, "I hope not."

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Shortly after the AFL-CIO forum, Hillary Clinton arrived at Grace O'Malley's Grill & Tavern in the South Loop to greet the 150 supporters who had come for a debate-watching party. She showed up to deliver a short pep talk and to schmooze with the crowd, but first, she also had other business at hand: signing the formal papers declaring her candidacy in the Illinois primary. In a ceremony carefully choreographed for the local media, Clinton's old childhood pals joined the candidate, and one by one hugged her. The only thing missing was a Cubs hat. It was a poignant tableau—a moment not lost upon Clinton. "This is so exciting," she exclaimed. "Oh, my goodness—wow. This is fabulous." As Clinton drew her pen and was about to sign, Clinton's high-school buddy Betsy Ebeling told the group that she had cried earlier that day after seeing her best friend's name for the first time on the presidential nomination petitions. Everybody clapped, and Clinton paused for a moment, and then, looking at Ebeling with puppy-dog eyes, said to her, "You're going to make me cry."

And then she signed the papers, with a big grin.

This article appears in the October 2007 issue of Chicago Magazine.

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