He's number one! Credit: Richard A. Chapman/Sun-Times

When Jesus “Chuy” Garcia announced last October that he was challenging Rahm Emanuel for mayor, the incumbent had already raised nearly $10 million for his reelection bid. An affiliated political action committee, Chicago Forward, had collected about $2.5 million more, according to state records.

As it turned out, that wasn’t the half of it—literally. By the time Emanuel won with about 56 percent, his campaign had raked in around $21 million total and his super PAC another $5 million. Inevitably, the runoff was depicted as “the cash vs. the ‘stache.”

There are, no doubt, a sizable number of Chicagoans who support Emanuel and would have voted for him regardless of who he was running against. But he was hardly the most popular man in town for most of his first term, in part because so many ordinary Chicagoans viewed him as Mayor 1%, who cared only about the rich and clout-heavy few.

In the end, though, it was the well-to-do—investment bankers, hedge fund managers, and Hollywood moguls—who poured in the lion’s share of the money to help him shape the public’s attitude.

The old Democratic machine had armies of patronage employees to deliver the vote. The new political system that controls City Hall is based on a network of wealthy campaign donors. Here are five ways that system helped Emanuel hold on to his seat.

Money helped him get the job in the first place

Most Chicagoans were taken by surprise when Mayor Richard M. Daley announced in September 2010 that he wouldn’t run for another term. But Emanuel moved fast. That day he created a new campaign fund, Chicagoans for Rahm Emanuel, and transferred more than $750,000 into it from his old congressional campaign. Then he started dialing for dollars. Within a week he had collected $2 million more, which he used to start setting up a campaign—and, just as importantly, to ward off potential rivals, including Cook County sheriff Tom Dart and Congressman Danny Davis, who both explored the race before bowing out. Emanuel’s fund-raising total rose to more than $13 million before the election in February 2011, when he won in the first round of balloting.

Money helped him clear the field again

By the midpoint in his first term, Emanuel’s school closings, handling of crime, and top-down style had battered his approval ratings. Chicago Teachers Union president Karen Lewis and other critics began looking for someone who could take him on—and then kept looking. Once again, Dart took a pass. So did Illinois attorney general Lisa Madigan. Emanuel’s progressive foes took heart as Cook County Board president Toni Preckwinkle made it clear she didn’t think much of the mayor’s school closings. But after dithering for more than a year, Preckwinkle said no thanks last summer. In each case, the potential candidates knew they’d be going up against a well-funded campaign operation that would blast them with negative commercials—and their allies, funders, and families could be attacked too. As one progressive elected official told us: “If you put your dick on the table, they’ll cut it off.”

Money helped him win over President Obama

Emanuel didn’t purchase the president’s endorsement as if it were TV time for a campaign spot. It’s more that the president is a prudent and practical politician who understands Emanuel’s ties to the Democratic Party’s national fund-raising machine, a nexus of donors from Wall Street to Hollywood who will be called upon again to help Hillary Clinton if she decides to run. So even though President Obama subtly ushered him out of the White House back in 2010, and there’s clearly no love lost between the mayor and Michelle Obama, the president made a point of flying to town to appear with Emanuel at a campaign rally. Obama had barely returned to Washington before a clip of them hugging was turned into a commercial. Along with an Obama radio spot—which seemed to run around the clock on south-side talk station WVON—the image of the presidential embrace made it exceedingly difficult for Garcia to cut into the mayor’s black vote, school closings be damned.

Money helped him counterattack Chuy

From the start, Garcia was largely unknown to everyone too young to remember—or too conservative to care about—his role as an activist and alderman allied with former mayor Harold Washington. In short, to anyone under the age of 60 or to the right of Rachel Maddow.

That meant for many voters Garcia was a blank slate. And the mayor was like a teenage tagger, eagerly spray painting his message onto that open space. In commercials and flyers, Rahm blasted Chuy for being a know-nothing rookie, in over his head, without a plan to deal with Chicago’s looming pension crisis. The mayor left it to his supporters—like Senator Mark Kirk—to drop the dreaded D-word, suggesting that a vote for Chuy was a vote for turning Chicago into Detroit.

Even when the Motor City wasn’t explicitly mentioned, the dire warnings of what could happen under Garcia locked up the votes of panicky north-siders. Garcia eventually raised $6.2 million—mostly from unions—that allowed him to get campaign ads on TV, but the media had already picked up on the theme that he was the man without a financial plan. Of course, Emanuel was nearly as vague, but his friendships with rich guys were now alluded to as an asset. As Kirk put it, the mayor can “command the respect of the bond market”—though the city’s bond rating has actually gone down on his watch.

Money helped him craft a whole new story, over and over

With no intended irony, the mayor officially launched his reelection campaign with a choreographed rally at a west-side film production studio. It signaled how he would make his case to voters in speeches and ads that were essentially a greatest-hits collection of his talking points from the previous four years, touting the “tough decisions” he’s made to lengthen the school day, move cops from desk to street duty, and create jobs. And of course he repeatedly highlighted his successful effort to hike the city’s minimum wage to $13 an hour by 2019.

After he failed to win a majority in the first round of balloting in February, Emanuel went back to his donors for more help. And they responded: over just the last six weeks, his campaign fund hauled in close to $6 million. Chicago Forward received another $2.3 million.

Flush with campaign cash, Emanuel released a series of ads intended to show that he got the election message. In one, he appeared in a V-neck sweater and admitted that he isn’t always such a great listener—but then said it’s all in the interest of “fighting for Chicago and Chicago’s future.”

In other words, he used his money to tell voters that they could find common ground on one key point: that he may be a jerk, but at least he’s Chicago’s jerk.  v