CHICAGO—It's just days before a heated election to determine Illinois' next governor, and Republican Bruce Rauner is in Chicago's South Side. He wants to know what issues matter to a convicted felon who served 22 years for laundering drug money.

They're at Fleck's Coffee, a year-old business in the working-class Chatham neighborhood, just blocks from where some of the worst violence in the city has taken place. Rauner listens as Joseph Davis, who runs an organization that helps former felons find work, and a group of black ministers—many of whom have endorsed the Republican—talk about crime, drug sentencing, and challenges for black-owned businesses.

The 57-year-old venture capitalist doesn't look out of place. But he isn't in his element either. He nods his head when Davis argues that felons need a chance to "reestablish themselves" when they get out of jail. Davis entered the meeting undecided, but said he left as a supporter of Rauner's.

When the Rev. Corey Brooks, an African-American pastor who endorsed Rauner, expresses concern about rampant unemployment in Chicago, Rauner sounds an empathetic note: "I don't see enough stores and businesses owned by African-Americans. There's a lack of economic opportunity and a lack of economic empowerment," he replies. For the most part, Rauner listens, and speaks in carefully practiced sound bites.

"African-American families today are suffering terribly with unemployment, poverty, crime, low wages, lousy schools, shredding social services. [Gov. Pat Quinn has] failed the African-American community, yet he's taken their vote for granted," Rauner tells me after the breakfast meeting. "He's assuming African Americans are voting for him even though he doesn't deserve to get their vote."

It's part of an unconventional strategy for Rauner, a billionaire venture capitalist who is spending time in an overwhelmingly African-American community that gave nearly unanimous support to President Obama and instinctively votes Democratic. Several prospective Republican presidential candidates, including Paul Ryan and Rand Paul, have engaged in minority outreach, but it has been rare for top Republican candidates to make it such a prominent part of their strategy in the final stage of an actual campaign.

Rauner is doing just that. Locked in a tight race with a Democratic governor, Rauner's campaign is convinced that if he can get about 15 percent of a usually-monolithic black vote, he's got the election locked up. "Pat Quinn is taking the African-American vote for granted. He's talking, but he's not delivering results!" he thundered at a debate that night cosponsored by the Chicago Urban League.

Rauner used the opportunity to tout the endorsement he received from the black ministers he'd met in the morning, while outside the debate hall dozens of Rauner's African-American supporters, brought in by the campaign, shouted epithets at Quinn.

"I've been a Democrat all my life," says Davis, now in his 60s, wearing a grey suit with a crucifix lapel pin. "I found out that just being a Democrat is not enough. I'm for whoever's going to help the community." He added: "Democrats have become so arrogant that they think they're the heir to black votes. We're not your children."

Democrats are perplexed by Rauner's strategy, assuming it's as much a play to win over moderate suburban white voters as it is to actually win over black votes. Even one in-state Republican operative wondered why Rauner was spending valuable October campaign time in overwhelmingly Democratic precincts, given that he needs to win over undecided suburbanites in more politically-competitive territory.

"What Rauner is trying to do is taking a 90-10 electorate, and making it 88-12," said a former adviser to Rahm Emanuel about the Republican's focus on black voters. "That's a waste of your time when there's a 60-40 [suburban] electorate that you can make 50-50."

In the three days I spent with his campaign in mid-October, the campaign stops Rauner made were all in minority areas of Chicago—the coffee shop on the South Side, a café on the city's heavily-Hispanic West Side, and at a popular Chinese restaurant in Chinatown. The vast majority of voters who attended the events were small business owners and religious leaders—two professions where Republicans perform well with white voters but still lag badly with minorities.

"Many Democratic politicians take the Latino vote for granted. They talk about Latino issues but they don't change anything for Latino families. And they don't create the real opportunity for the American dream. We're going to change that," Rauner said while campaigning at La Catedral Café on Chicago's West Side. He offers an entrepreneurial message focused on economic opportunity and education reform—that with hard work and a helping hand, anyone can succeed—sprinkled with sharp criticism of Gov. Quinn for the insidiously high unemployment rate in the minority communities throughout Illinois.

Tony Hu, the owner of the popular Lao Shanghai restaurant in Chicago's Chinatown, said the Republicans' last gubernatorial nominee, conservative state Sen. Bill Brady, made a last-minute visit to his restaurant in 2010 asking for his vote, but never engaged in any prior outreach to him or the Chinese-American community in Chicago. Rauner, by contrast, schmoozed with him when they were both part of a 2011 trade delegation (that included then-Mayor Richard Daley), and forged a relationship. Rauner kept in touch after the trip, occasionally visiting the restaurant with his family. Hu said that past engagement played a pivotal role in his support and advocacy for Rauner's campaign.

"Bruce has roots with us. I'm not a political person, I'm a community servant. But I look at someone's past. He has the ability. Look at his background. And vision," Hu said. "We don't care about Democrats or Republicans. We care about who has ability. Bruce, he has ability."

HIGH STAKES IN ILLINOIS

Even though it hasn't garnered a level of national attention on par with battleground Senate elections, the Illinois governor's race is as consequential a contest for Republicans as any other in the country. It's something of a political science experiment, testing whether Republicans have a chance to make even small inroads with minority communities.

On paper, Rauner is an appealing Republican candidate for such a mission. He has a long record of philanthropy to minority communities, even before he began his second career in politics. He was the main donor for several urban renewal projects, including a YMCA in the majority-Hispanic Little Village neighborhood and six new charter schools on the city's West Side. His work in education-reform circles has opened up a partnership with leading African-American community leaders and clergy that he's utilized in the gubernatorial campaign. He's a friend of the Rev. James Meeks, minister at Salem Baptist Church, one of the largest black churches in the city. They've gone fly-fishing together on vacation. He talks about his endowment of a professorship at historically black Morehouse College. He tapped a Latina running mate, attorney Evelyn Sanguinetti, whose experience as a first-generation immigrant is a story he highlights when speaking to Hispanic groups.

"Our outreach effort has been like no other. Businesses of every kind are suffering. So we're reaching out to Latinos, to the Indian-American communities, the Polish community, the Russian communities," said Sanguinetti. "As Republicans, the messaging is out there now. Before, I believe we had problems with messaging. But that's no longer the case. The party has a face-lift."

Last Sunday, Rauner even spent the second-to-last weekend on the trail at the New Beginnings Church of Christ on Chicago's South Side. "Our Lord God has not put us on this Earth as Democrats and Republicans," he told the congregation, according to the Associated Press. "He put us on this Earth to take care of each other."

Meanwhile, he's running against one of the least popular governors in the country, who has presided over a state with unemployment rates among minority communities well above the national average. Bill Brady, Quinn's last Republican opponent, won just 6 percent of African-American voters and 26 percent of Hispanics in the last gubernatorial election. Quinn won the race by a 32,000-vote margin out of 3.4 million votes. This year's race is shaping up to be as competitive.

One of Rauner's ads, specifically aimed at the black community, features footage of former Chicago Mayor Harold Washington in 1987, saying he regretted hiring Quinn as the city's revenue director. "He was dismissed and he should've been dismissed," said Washington, who was the city's first black mayor. "My only regret is that we hired him and kept him too long."

Quinn's campaign has been bludgeoning Rauner on the airwaves, portraying him as a vulture capitalist who laid off workers and shipped jobs overseas, and even unleashed allegations that he threatened a female manager because she declined to lay off employees.

That Democratic assault might be working. Talk to strategists with both campaigns, and Rauner hasn't made the gains with minority voters that he expected, despite his effort. He's facing a challenge hitting 10 percent support among black voters, and isn't improving much on Brady's Hispanic performance, either. In fact, the Chicago Tribune poll released last week has him winning only 3 percent of the African-American vote, just half of Brady's showing in 2010.

"He'll be lucky to get what Brady got," said Quinn pollster Mark Mellman. "Across the state, including the African-American communities, [people] see him for what he is—a guy who makes himself rich in shady business deals at the expense of everyone else. That's not what people want in a governor."

A SUBURBAN AUDIENCE

Even Republicans working for Rauner privately acknowledged that despite their candidate's optimism, they're not going to reshape long-standing voting patterns that have consigned Republicans to a sliver of the black vote. His campaign has set a goal of winning 20 percent of the vote in Chicago, something that can be accomplished with only small inroads among minority voters. But they also hope that by highlighting Rauner's minority outreach, he'll improve his showing among softer Republican voters—like married women in the suburbs and moderates. The Chicago Tribune poll, which showed Rauner narrowly ahead, reported that his gains had "been driven primarily by white suburban women, a voting bloc considered socially moderate but fiscally conservative."

Indeed, Rauner is part of a leading wave of candidates who are beginning to engage in minority outreach, even if it doesn't render immediate political dividends. Republican National Committee chairman Reince Priebus has prioritized minority outreach in the run-up to the 2016 presidential election, and has opened field offices meant to reach African-American voters in Ohio, North Carolina, Michigan, and Florida.

In Louisiana, Republican Senate candidate Bill Cassidy has discussed his work as cofounder of free dental and health care clinics for the uninsured—many in heavily black neighborhoods. Cutting into Sen. Mary Landrieu's huge support within the black community would be devastating to her already tenuous reelection hopes. Early in the cycle, Sen. Marco Rubio's political action committee aired Spanish-language ads in support of Republican Cory Gardner in the Colorado Senate race. Representing a swing seat, Republican Rep. Mike Coffman has become omnipresent throughout his cosmopolitan suburban Denver district, from Korean community meetings to Hispanic groceries.

"When I worked for Rudy Giuliani, we recognized we never were going to get the votes from the Dominican community, but we did that outreach because it was important to do. Doing well while doing good. It's the model that Rauner's picked up," said Republican media strategist Rick Wilson, who cited the former New York City mayor as one of several Republicans to aggressively engage in minority outreach in the late stages of a campaign. "You know [they] may not vote for us, but it shows we're listening. It doesn't cost you much to see you're on a long march."

Quinn isn't taking the threat against his base lightly. President Obama headlined a mid-October campaign rally in Illinois earlier this month at Chicago State University, designed to bring black voters to the polls for the governor. "You got to find cousin Pookie. He's sitting on the couch right now watching football—hasn't voted in the last five elections. You've got to grab him and tell him to go vote… And then tell them to vote for Pat Quinn," Obama said. Obama's numbers are barely above water even in his home state, but he's still an effective surrogate for turning out African-American voters.

For Republicans, the outreach to minorities is as much out of necessity as it is out of beneficence. Mitt Romney scored an historic high for a GOP presidential challenger by winning 59 percent of the white vote in the 2012 presidential election, but his dismal showing among minorities relegated him to just 47 percent of the overall vote. With the share of minority voters increasing over time, Republican officials recognize they are destined to struggle unless they can make real inroads into communities that don't traditionally vote for them.

At the same time, if Republicans are able to take even a small bit of constituent groups that are overwhelmingly Democratic, it could be the basis for a longer-term winning coalition. Democratic struggles with working-class white voters have cratered in the second term of Obama's presidency, and have given Republicans an opening to win over disaffected voters who don't usually vote for their party.

"We need to position the black community to take advantage of the opportunities that will emerge as Republicans will need to broaden their appeal," said the Rev. Marshall Hatch, a friend of Al Sharpton's, who regularly votes for Democrats but is backing Rauner in this election. "Illinois has become like a one-party state, and it's not healthy. We need to be more sophisticated in our politics. We can't be effective if we're in the hip pocket of one party."

This article appears in the October 29, 2014 edition of NJ Daily.