Illustration: Jason Seiler

A couple of hours before Hillary Clinton squared off against her Democratic primary rivals at the AFL-CIO–sponsored presidential debate held in August at Soldier Field, a few dozen of her ardent volunteers, clad in blue "Hillary for President" T-shirts, gathered at a card table outside the stadium. With the temperature near 90 degrees, they huddled beneath the beating rays of the summer sun to begin the petition drive to get the New York senator on the Illinois ballot. Soon, 15,000 or so union members were lining up to enter the stadium: an ideal pool in which to fish for the 3,000 signatures Clinton needed. While the volunteers signed up supporters, the cochairman of Clinton's nationwide grassroots organization, J. B. Pritzker, the billionaire heir to the Hyatt hotels, passed out bottled water to his helpers.

Meanwhile, just a football field away, at the stadium's far south parking lot, Senator Barack Obama's campaign held a get-together of its own: a big tailgate rally, with 500 or so supporters, clapping to the Bears' fight song, "Bear Down, Chicago Bears!" Obama's campaign was also collecting signatures, but just for its volunteer rolls.

The crowd that turned out for Obama's rally had Clinton volunteers feeling outnumbered but not discouraged. In just a couple of hours, the Clinton team says, it collected around 800 signatures for its nominating papers. "It was really important to us to use the AFL-CIO debate to actually get some real work done, instead of just screaming for our candidate," says Stacey Zolt Hara, a former press secretary for U.S. Senator Dick Durbin who is helping Clinton's campaign with its local press operations. "We're very much a substance-over-style campaign."

Maybe so, but the differences between the two campaigns in Illinois could also be summed up another way—the same way one Obama supporter put it on a sign he held up at the Soldier Field tailgate rally: "Home field advantage."


With a commanding double-digit lead in many early nationwide pre-primary polls, Hillary Clinton is widely viewed as the presumptive Democratic presidential nominee, at least for now. But here in Illinois, despite her hometown roots in Park Ridge, and even with the powerful, deep-pocketed local political network she formed during her eight years as First Lady and six as a U.S. senator, Clinton finds herself in an unusual position: as the underdog—fighting what her backers are calling an "insurgent campaign" against the state's favorite son. It's hard to tell how "underdog" she really is: Early polls in Illinois show that Clinton is trailing Obama here, but not by much, and seems to be gaining on him, though many pundits and insiders dismiss such early surveys. 

In any case, the race has many Illinois Democrats feeling deeply divided, even those who have already taken sides: Do they go with their old friend Hillary, whom they've followed through the highs and lows of Clinton campaigns and the Clinton White House, or stay loyal to their home-state senator? U.S. representative Bobby Rush (1st) chose Obama early on, but told the press at the time that it was "one of the most difficult decisions that [he's] had to make in politics." The intense competition has divided families—witness the Pritzkers: J. B. Pritzker's older sister, Penny, is Obama's national finance chairwoman. The race has also proved awkward for the Jackson clan. Reverend Jesse Jackson and his congressman son, Jesse Jr. (2nd), are in Obama's camp; Yusef, the youngest son, is going with Clinton, while the middle son, Jonathan, is still "undecided." When U.S. representative Rahm Emanuel (5th), a former aide to President Bill Clinton who is also close with Obama, was asked where he stood in the race, he reportedly replied, "I'm hiding under my desk."  (As of press time, in late August, he remained officially uncommitted.)

So far, the political establishment sides overwhelmingly with Obama—publicly, at least. Almost every Democratic elected official in Illinois—Mayor Richard M. Daley, Governor Rod Blagojevich, and Senator Durbin, to name a few—has endorsed Obama. Only a handful of elected officials, mostly political small fry compared with Obama's supporters, have come out for Clinton. State representative Jack Franks of Woodstock, for one, is the only state lawmaker to buck the Barack bandwagon so far, joined by lesser-known politicians like Aldermen Bernard Stone (50th) and Danny Solis (25th); Solis's younger sister Patti Solis Doyle is Clinton's national campaign manager.

Most of the state's best-known Democratic benefactors are already backing Obama, even a few longtime Clinton family friends who slept in the Lincoln bedroom or sipped coffee on the Truman balcony during the Clinton White House years—people such as Marc Schulman, of Eli's Cheesecake, Thomas Hynes, the former Cook County assessor turned lobbyist, and former commerce secretary William Daley. Lewis Manilow, who was Bill Clinton's Illinois campaign finance chairman in 1992, and gave $3,000 to Hillary for her New York Senate races, has pledged his support and his money to Obama. "Hillary's terrific—if she wins [the nomination], I'll support her," says Manilow. But he thinks Illinois will be solidly behind its hometown senator come February 5th, primary day. "If I were Hillary, I wouldn't waste my time here," he says. 

Obama had also outraised Clinton by a margin of more than four to one in Illinois—$6,907,641 to $1,717,370—after the first six months of the campaign, according to Federal Election Commission records. (By comparison, Clinton held a little more than a two-to-one fundraising edge in New York, $13,808,121 to $5,828,524.) The fundraising gap in Illinois was at one point even larger; after the first three months of the campaign, Clinton had raised next to nothing here—a meager $373,432 to Obama's $3,742,757.

Other local Democratic bigwigs have tried to stay neutral. Some are hedging their bets by giving cash to both candidates or they are sitting out the primary race entirely, not wanting to choose sides. "I'm kind of staying out of it," says North Shore businessman Lou Weisbach, a major Democratic donor, who has doled out nearly $850,000 to Democratic candidates and party committees since 1990.

Although Obama has lured most of the Clinton network's longtime local supporters, Hillary's list of political friends and upper-echelon donors still makes up an impressive roster. It includes the television mogul Fred Eychaner, one of the nation's heaviest-hitting Democratic donors, who has written checks totaling more than $8 million since 1990; Kendall College president Howard Tullman, another top-tier donor; mega-lawyer Myron Cherry, a major so-called bundler of campaign donations; talk show host Jerry Springer; and Ted Tetzlaff, chairman of the McPier authority.

But some Clinton backers are finding it tough being on the "wrong" side of the campaign. "It's kind of dicey—there are people who consider you a traitor or a Judas," says Valerie Alexander, Senator Durbin's former Chicago chief of staff, who initially supported Obama but switched after Clinton's strong performances in the early debates. "If you meet somebody and say, 'I'm for Hillary,' they look at you kind of puzzled, like, 'How can you do this?' There's this automatic assumption that you're supposed to be supporting Barack." Alexander's husband, Michael, a lobbyist and also a former Durbin aide, surely thought so. A staunch Obama supporter, he thought his wife was joking when she announced her switch. "And when it became clear that she wasn't kidding," he says, "in all honesty, it was a little awkward. For the first time in the four years or so that we've been married, we've kind of started talking about the weather; presidential politics became a little taboo." 

Valerie Alexander felt particularly anxious about telling her old boss and political mentor, Dick Durbin, one of Obama's most vocal boosters. "I couldn't just pick up the phone and tell him—I didn't want to appear disloyal," she recalls. Instead she broke the news in an e-mail to Durbin's wife, Loretta, asking her, "How can I tell Dick that I'm with Hillary without him punching me in the face?"

J. B. Pritzker knows how that goes. "You get the feeling that you're in a bubble here," he says. "It's strange, 'cause I talk to my friends at the Obama campaign and they're like, 'Oh, isn't he doing great?' And I'm like, 'Actually, why don't you head over the border to Wisconsin, where she's up 15, 20 points, whatever the latest are, and then you'll get a sense for how he's doing nationally.'"

Clinton herself, who was born in Edgewater and lived in Park Ridge through high school, has vowed to challenge the Hawaii-born Obama on what is now considered his home turf. "I am not ceding any voter, anywhere, to anyone," she told local reporters in May, during a campaign stopover in Chicago. She added: "I don't consider Chicago or Illinois off limits to me."

Certainly, it used to be just the opposite: Before Illinois got swept up in Obamamania, the state—particularly the Chicago area—was true-blue Clinton Country. Bill Clinton defeated George H. W. Bush (and Ross Perot) in 1992, collecting 49 percent of the statewide vote and 72 percent in the city. Four years later, he won re-election with 54 percent support in Illinois and nearly 80 percent citywide. Donors in the state have been big supporters of both of Hillary's Senate campaigns—even after the lifelong Cubs fan donned a Yankees cap before her first race in 2000. In that election, Illinois Democrats gave her $717,000, fifth most among all the states. And last year, Illinois donors fattened her campaign coffers by more than $887,000.

"The people in Illinois who are choosing to go with Hillary Clinton are choosing to do so because they've known her for a long time," says Pritzker. "She's a homegrown girl. She's a favorite daughter. If there's anybody in this race that can also claim favorite status here, it's her. She loves Illinois, and she would like to win Illinois."


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." 


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."


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.