Emanuel’s campaign focused on rebranding him as a Chicago guy, kind of like the Daleys—who, for all their wealth and power, still oozed the South Side, rough-spoken Bridgeport neighborhood from which they hailed. The campaign played up the ties Emanuel did have to working-class Chicago: His life until fourth grade in an apartment in the Uptown neighborhood. Sunday evenings at his grandparents’ Chicago home, in an unspecified location near a big park. His maternal grandfather, Herman Smulevitz, who came to Chicago as a child fleeing religious persecution. His Uncle Les, a twenty-three-year veteran of the Chicago Police Department. The Chicago Reader noted that a slick, lengthy campaign mailer mentioned Emanuel’s investment banking not at all but devoted a full page to Uncle Les.17
Even a decade before “Wall Street versus Main Street” and “the 99 percent” became popular memes, Emanuel knew that voters might be turned off by the knowledge of his quick millions. So in November 2001, his staff conducted a focus group of male voters, paying them $75 each to describe how they felt upon hearing that Emanuel had become rich by “setting up deals.”
Emanuel’s wealth dwarfed that of Kaszak, who released tax returns showing she had earned $203,000 in the previous two years and had assets between $64,000 and $260,000.18 Emanuel ultimately spent $450,000 of his own money on the campaign, along with generous contributions from his corporate and political backers. Kaszak got substantial support from the organization EMILY’s List, which backs prochoice women candidates.19 But she was still outspent by Emanuel: he would raise almost $2 million during the primary campaign, compared to Kaszak’s $888,000.20 The funding gap was especially damaging when it came to expensive television ads: Emanuel started airing them in mid-February, but Kaszak couldn’t afford air time until the final week before the March 19 primary.21
As if his money and Machine backing weren’t formidable enough, Emanuel also turned out to be a surprisingly effective campaigner in his first run for elected office. He had long been known as obnoxious, abrasive, and impatient—hardly qualities that lend themselves to kissing babies and empathizing with senior citizens. But reporters and pundits remarked upon his friendly, charming demeanor and his ability to connect with voters as he put in long hours at L train stations, senior centers, grocery stores, and other public places.22 Perhaps Emanuel had picked up some tips from his former boss Bill Clinton, famed for the ease and enjoyment with which he moved among regular people.
Emanuel secured the endorsement of the Chicago Teachers Union, which would become his nemesis a decade later. The Illinois AFL-CIO also endorsed him after some nail-biting among Emanuel’s people over whom the labor federation would choose. Emanuel found out he’d secured the AFL-CIO endorsement during a breakfast interview with Reader reporter Ben Joravsky, and the newly warm-and-fuzzy candidate was so happy he jumped up, hugged, and gave a noogie to “my new best friend,” as Joravsky told it.23
Kaszak had a 94 percent approval rating from the AFL-CIO, but apparently Emanuel’s clout and Washington connections trumped her more grassroots and state-level credentials. The Nation quoted Illinois AFL-CIO political director Bill Looby saying, “She had the good labor record, but he had the record of knowing his way around Washington. The feeling was, he could be more effective in Washington.”24
Emanuel’s role in NAFTA apparently didn’t sway the AFL-CIO to support Kaszak. But EMILY’s List spent $400,000 on Kaszak’s behalf, funding ads that hammered Emanuel’s central role in NAFTA and noted that the trade agreement had cost Illinois eleven thousand jobs.25 (Emanuel media adviser David Axelrod, who would later serve as a top campaign adviser and then senior adviser to President Barack Obama, decried the ads as unfair attacks.)26 Kaszak’s campaign also spotlighted Emanuel’s involvement with welfare reform and the controversial merger that created the energy company Exelon.27
Meanwhile, Emanuel lambasted Kaszak for being soft on crime, invoking several state legislative votes wherein she appeared to oppose stiffer sentences for criminals. Kaszak’s campaign manager was Chris Mather, who would become Emanuel’s communications chief during his run for mayor. Responding to Emanuel’s line of attacks, Mather told the Chicago Tribune, “Anyone can take a vote or two out of context, out of thousands of votes taken, and try to distort someone’s record. . . . Rahm is an opposition researcher at heart and this is the type of negative thing you’re going to get from that type of individual.”28
One endorsement Emanuel failed to get might have stung: his old employer the Illinois Public Action Council decided to endorse Kaszak. At the time Emanuel worked there, researcher and strategist Don Wiener worked for Citizen Action, the national group with which the council was affiliated. By 2002 Wiener was an Illinois Public Action Council board member. Wiener had been a leader of the grassroots national labor and community coalition opposing NAFTA when Emanuel shepherded it through during Clinton’s presidency. He had promised to help secure the council’s endorsement for Kaszak before Emanuel entered the race. Outside the Illinois Public Action Council board meeting where Emanuel made his pitch for endorsement, Wiener remembered him saying breezily, “Wiener, you’re wearing the same clothes you were wearing last time I saw you”—which may have been more or less accurate, because Wiener was wearing his trademark jeans and leather jacket. Emanuel’s words could be seen as a friendly signifier of familiarity, but Wiener took it as an intentional and clever jab that “you’ve stayed in the same place—you’re still a community organizer—and look where I’ve gone.” “He’s a genius in insulting people,” Wiener said.29
A Slugfest and a Slur
In early February 2002, Bill Clinton came to Chicago to campaign for Emanuel. Clinton headlined a $100-a-ticket fundraiser at the Park West auditorium and a $1,000-per-person reception at a private lakefront home. At that point Emanuel had almost $1 million in his war chest, while Kaszak had less than $65,000.30 But Kaszak remained at least outwardly confident, saying, “The people of the Fifth Congressional District cannot be bought.”31
Kaszak was still hanging on to her lead in mid-February; one poll showed her ahead of Emanuel 33 percent to 18 percent.32 By early March, though, her lead had evaporated, and the two candidates were neck and neck. One poll found one in four voters still hadn’t made up their minds, and Emanuel led Kaszak by a statistically insignificant margin of 35 to 33 percent.33 A Chicago Sun-Times editorial called the race “a slugfest in the grand Chicago tradition, between grass-roots activist Kaszak and Washington insider Emanuel.”34
So Kaszak could hardly afford the gaffe that occurred just two weeks before the election. Casimir Pulaski Day should have been a good one for Kaszak. It is an annual holiday commemorating the Polish-born Revolutionary War hero, usually celebrated with fairs and official events in Chicago’s Polish neighborhoods. Ed Moskal, president of the Polish American Congress community group, ardently wanted Kaszak to win the seat. So Moskal presumably thought he was helping when he declared at a Pulaski Day event that Emanuel was an Israeli citizen who had served two years in the Israeli army. He took things even farther, decrying Polish American Emanuel supporters by saying, “Sadly, there are those among us who will accept thirty pieces of silver to betray Polonia.”35
Both statements about Emanuel were false, and Moskal’s address was viewed as virulently anti-Semitic, eliciting condemnations from Jewish groups.36 Kaszak was in the crowd but didn’t immediately comment; she later said she had been distracted and didn’t hear much. Once she heard the full remarks, she denounced the speech and demanded Moskal apologize. He refused.37
Emanuel called Moskal’s statements “deplorable,” and he accused Moskal of orchestrating an anti-Semitic “whispering campaign” with Kaszak’s knowledge and tacit support.38 A spokesman for the Polish National Alliance made things worse by trying to justify Moskal’s comments, saying they were just “born of frustration with Jews.”39
The day after the festival the Emanuel campaign hosted a press conference of religious leaders to denounce Moskal’s statements. A desperate Kaszak showed up pleading to make her case. Emanuel campaign staff