As he attempts to unify the city and rebuild trust, Mayor Rahm Emanuel is encountering a number of wedge issues he’ll need to overcome if he wants a third term, say community leaders across the city. From the recent election of Donald Trump as president to the upcoming gubernatorial race in 2018, these wedge issues will likely intensify in the years leading to the 2019 mayoral race, forcing Emanuel to make new allies and tough political choices.

First, there is an increased uncertainty and anxiety among the Latino voters in Chicago, who fear that Trump will follow through on some of his most radical anti-immigration ideas. Yet, according to those we spoke to, Emanuel has a poor record among Latinos on immigration himself. He is viewed as one of the main roadblocks to immigration reform as Chief of Staff to President Barack Obama, who is also known for increasing deportations.

Second, Emanuel has struggled to get cooperation from his one-time friend, Republican Gov. Bruce Rauner, to help bridge some of the city’s biggest funding gaps, including for Chicago Public Schools. Rauner, deep in an ideological battle with Democratic legislators, has turned the budget screws even tighter for Emanuel.

Finally, the mayor opted to dramatically increase city taxes and fees to fund city worker pensions, after years of pension holidays. But Gov. Rauner hasn’t approved the payment plans for municipal and labor pension plans, making city workers uneasy, and leaving voters across the city wondering where their money is going, and bracing for the next round of increases.

The Neighborhood Perspective: A Five Part Report From The Daily Line

Monday, Part 1 – Community Leaders: Frustrated With Emanuel Administration, But Waiting, Hoping For Improvements

Tuesday, Part 2 – A New Group Of African American Influencers Taking The Stage

Wednesday, Part 3 – Challenges For Mayor Emanuel: Trust, Violence And Development

Thursday, Part 4 – Chicago’s Wedge Issues And Emerging Challengers

Friday, Part 5 – Their Words: Raw Comments From Our Interviews With Community Leaders

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This report, the fourth in a series, is the result of interviews with ground-level organizers from every corner of Chicago. Over sixty pastors, not-for-profit leaders, former aldermanic campaign staffers, a popular local restaurant manager, activists, precinct captains, and fundraisers were  interviewed in an effort to obtain a sense of Chicago’s biggest political challenges.

Wedge Issue 1: Immigration

Since Donald Trump’s election to the presidency, Mayor Emanuel has made numerous public statements defending Chicago’s status as a sanctuary city for immigrants. He personally delivered a letter to the president-elect “urging him to continue the Deferred Action for Childhood Arrivals (DACA) Program until Congress modernizes the immigration system.” He allocated $1.3 million toward a new legal defense fund that’ll provide outreach, education and assistance for immigrants faced with the threat of deportation. Along with U.S. Senator Dick Durbin and Cong. Luis Gutierrez, the mayor also created a task force that will develop a comprehensive website detailing mental health, legal, and job training resources for undocumented residents. And in the 2017 budget, the City Clerk’s Office received a $1 million appropriation to design and unveil a new Municipal ID program in the hopes of better connecting immigrants to city services.  

“For Latinos, he’s been such a champion for the sanctuary city. It’s going to play big that he’s been a vocal advocate for their current and future well-being. Regardless of your politics, for me it’s a humane issue,” said Craig Chico, Executive Director of the Back of The Yards Neighborhood Council. “In this part of town it plays pretty big.”

Beyond the Latino community’s concerns about increased deportations, concerns about President-Elect Trump’s threats to Chicago weave through practically every community leader’s concerns, providing Mayor Emanuel with a convenient foil.

“I think that the fear in the communities right now is that the Democrats, although as imperfect as they may be, they’re the protectors of the immigrant community,” said Manny Diaz, a former campaign manager for 15th Ward aldermanic candidate Rafael Yañez. “And I think that fear goes to his favor because of his stance that he is taking with [Congressman] Luis Gutierrez and other well known Latino leaders. I think that the Latino vote would overwhelmingly go to him.”

If true, this would be major constituency for Mayor Emanuel at a time when his favorability is at an all time low among the African-American community in the wake of fractured community-police relations. Chicago politics has long history of racial division, with constituencies broken up into three major fractions: White, Black, and Hispanic. Mayor Emanuel won his second term by gaining a majority of votes from two of those factions: the lakefront and downtown majority-white voting bloc coupled voters from majority African-American wards on the South and West Side. Hispanic strongholds, which stretch along the city’s Southwest and Northwest Sides, largely went for Emanuel’s challenger, Cook County Commissioner Jesus “Chuy” Garcia.

“We have to be realistic about the fact that black and Latino racism is real against each other,” explained an African-American politico from the South Side. “If they don’t know you, they go with the devil they know.”

“A lot of the progressive leaders and on the North Lakefront, they are so concerned about the Trump policies on immigration, there’s an opportunity for the mayor on down to come together. You would hear quite a bit about that on the North Lakefront,” said North Side political consultant Sean Tenner.

While Emanuel is framing himself as a big supporter of Chicago’s undocumented immigrants today, some Latino leaders have not forgotten that as chief of staff for President Barack Obama and an advisor to President Bill Clinton, Emanuel referred to comprehensive immigration reform as a “third rail” topic. A record number of people were deported from the U.S. during Obama's tenure as President, and some viewed Emanuel as a roadblock to reform while he was in D.C.

“In my mind, and in the Little Village community, he’s still vulnerable. In big pieces of the Little Village community, and it’s not lost that the kind of policies that Trump is advocating about immigration are not too far away from what Rahm himself was recommending to [President Bill] Clinton and everyone else, so he still has a lot of ground to cover there,” said Dion Miller-Perez, a Little Village-based political consultant who has worked on aldermanic campaigns. “A lot of people here blame Obama, or as they call Obama in the neighborhood, the ‘Deporter-in-Chief’...There seems to be a connection to things Rahm [Emanuel] has been saying and things Trump has advocated for. If you’re in the circles of people who are active politically, especially immigration activists, you hear that.”

“One of the biggest obstacles our community faces is we have a high concentration of undocumented people in our neighborhood. A lot of families are mixed status. Rahm is one of the main reasons comprehensive immigration reform didn’t pass, he advised Obama away from it,” one Southwest Side non-profit leader said, though they added many voters don’t know or have already forgotten.

“The average voter tends to forget easily. It was to his advantage that the Laquan McDonald video came out so early in his new term that in some way, voters have thought he’d done enough to overcome it. That’s the same thing with the immigration issue. If we made sure that part of history is not erased and we remember it, then people won’t vote for him. But if he figures out a way to change the narrative, we’re in trouble.”

President-Elect Trump’s victory could also have a chilling effect on police reform, some worry. The Department of Justice investigation into the Chicago Police Department will land after Trump’s inauguration with Alabama Senator Jeff Sessions likely at the helm as the country’s next Attorney General. As one nonprofit leader who spoke anonymously explained, “I think if we were going to try and get to some real conversations about police and community relations, we probably took some steps back once Trump won.” There will be less of a desire to talk about police misconduct or interaction if local law enforcement is working with Immigration and Customs Enforcement, she said.

Neighborhoods that have a high concentration of undocumented immigrants, like Back of The Yards, are anxious about the ripple effects this could have on the police department, as Diaz explained, “I think the fear is if Trump rallies around his promise to deport people in the community, are police officers going to serve as agents for him?”

“People are feeling incredibly insecure with the Trump administration coming in and the state is in such a shambles that people might...it’s all relative. Rahm looks perfectly reasonable next to [Gov. Bruce] Rauner and Trump,” said Jennifer Ritter, executive director of ONE Northside, a social services non-profit serving the Chicago North Lakefront.

“Who knows what it’s going to be like? Like I said, this is volatile, it’s still a volatile climate, and the fact that Trump is going to be president makes it more unpredictable than it was before. My sense is Rahm believes that because he’s not as bad as Trump that he will become more acceptable, and I don’t know if that’s true. I don’t know if people are going to make that fine distinction,” Miller-Perez said. “Leading up to November 8, people were saying ‘I’m going to vote for Hillary, but man, we really need to do something about Rahm.’ They’re still angry for him. Almost more angry now.”  

“I think the election of Trump suggests there’s some discontent. I hope we all take those results as an opportunity to reflect on the disconnect between politicians and the regular people,” said Byron Sigcho, a Pilsen activist. “Status quo politicians across the board will have a really hard time in re-election, surviving politically, if they don’t connect with the issues communities are facing.”

Wedge Issue 2: State Politics

When speaking to organizers and politicos across the city about the 2019 mayoral race, a significant number of those interviewed said they’re focusing their attention on another issue: pushing Republican Gov. Bruce Rauner out of Springfield. For these people, Gov. Rauner, not Mayor Emanuel, is the root cause for so much uncertainty in Chicago, from a lack of state funding for Chicago Public Schools and social services, to pension reform.

Said one politico from the far South Side, “You are going to have all the unions locally, nationally throwing money on the Governor’s race. I think that’s the big race. No one is talking about mayor. People who are thinking about the mayoral race in 2019 probably also have a vested interest in the governor’s race. Rahm is not stopping funding for social service programs like Rauner is.”

“[Mayor Emanuel] had a bad economic problem and Rauner made it worse,” added another South Side politico who has worked on aldermanic and county-wide races, suggesting that whoever runs for mayor will have to campaign with the backdrop of what’s expected to be an intense and expensive gubernatorial race. “Either you will have Rauner, who has been a terrorist to the city, or someone else. It’s very difficult to fix these problems in the city with a reckless governor.”

There’s also a continued movement, led by former Democratic Gov. Pat Quinn, to get mayoral term limits on the ballot when voters hit the polls for primary elections in March 2018. Their goal is to obtain 100,000 signatures by this time next year. Although it’s unlikely that long-standing Democratic lawmakers like House Speaker Mike Madigan or Senate President John Cullerton would ever allow such an initiative to make it on the ballot, some petitioners have been advertising the effort to voters as a way to block Emanuel from seeking a third term.

“It was really easy to get people to sign. We saw it as a referendum on Rahm [Emanuel],” said Pete DeMay, a one-time aldermanic candidate who is now active in the 12th Ward Independent Political Organization (IPO). “They’d say, ‘Oh this would term limit Rahm Emanuel? Where do I sign?’”

“The reaction that you got from these people is just like, ‘Yeah I don’t want Rahm Emanuel, f--- Rahm Emanuel.’ People just don’t like him… they don’t care who gets into office, they just don’t want him,” explained one canvasser, Myriam Perez, a student at Daley College who works with DeMay in the 12th Ward IPO.

Mayor Emanuel has had a rocky relationship with Gov. Rauner when it comes to getting state aid for city schools or amendments to the city’s pension payment schedule. While the mayor has touted his efforts to settle the city’s pension debt and put the four employee pension funds on a path to solvency, the state legislature and Gov. Rauner have yet to ratify the Mayor’s proposed changes to two of the four city pensions, of which city employees are very aware. For those workers and their families, which make up a significant vote on the Northwest and Southwest sides, pension solvency is paramount.

Wedge Issue 3: Increased Taxes And Funding Pensions

As state money has dried up, the city has been forced to turn to increasing property taxes and other fees to pay down its enormous pension debt. By 2019, Chicago will be paying over $1 billion a year into pensions and billions more in out years. Without a long-term solution, the mayor risks losing a massive voting bloc of city employees. But as city taxes go up, other voters lose patience with the mayor.

“I don’t know if he can mend relationships with cops, firefighters, and teachers. It’s all about pensions,” said one North Side political consultant who asked to remain anonymous. “If he could figure out a way to solve that so they weren’t getting screwed on their pension anymore, that would be one of the biggest steps he could do.”

Chris Vittorio, a former aldermanic candidate in the 41st Ward and Chief of Staff to current Ald. Anthony Napolitano, gave the mayor credit for raising property taxes for police and fire pensions, but said a perceived lack of support among police over accountability issues might be too much to overcome. “If he stands any chance to win reelection, you’re looking at 41 and 19. These are two of the heaviest voting wards, and they are a strong population of police and fire. The further he goes in the direction of more police accountability, the more scrutiny, the more votes he loses. I would not want to be in his shoes, but I give him credit because he’s making every effort he can.”

Meanwhile, homeowners across the city are already paying property tax hikes to cover the pension reforms, even those not yet approved by Springfield, providing Emanuel a Pyrrhic victory.

“We applied dutifully for our property tax rebate and we got our check for $325, and ironically, on the same day we got our new escrow notice, which is an increase of $375 a month. So we don’t even get a month from the rebate. And that’s all coming from our retirement savings,” said Thom Clark, an activist and radio host who lives in Rogers Park.

“You are getting hit hard with all these different taxes. You’ve got the garbage tax, you got the property tax, you got taxes that you have to pay now when you go to the store to use a bag, you’ve got the soda pop tax. They are taxing you left and right, and people aren’t as financially sound as they used to be. They are doing these things and it’s causing a big ripple, a tear within the African American community,” said retired Chicago police officer and one-time 6th Ward aldermanic candidate Richard Wooten.

Few Emerging Challengers

As increased violence, fractured relations with police and mistrust of the Emanuel Administration remain strong in predominantly African-American and Latino communities, while tax fatigue festers among all residents, it would seem that City Hall’s fifth floor is a reachable target for many in 2019. But as those interviewed for this series were quick to detail the obstacles Emanuel would need to overcome on his road to a third term, few could readily name a viable challenger.

The same names were repeatedly offered in our conversations, as were doubts that any could establish name recognition across a racially divided city, or the fundraising apparatus needed to challenge Emanuel.

“Unfortunately in Chicago we deal with name recognition before we deal with anything else. People vote people in because they know them, they know their name without even actually understanding what their platform is going to be or what they’re going to do,” explained Richard Wooten. “The road to the fifth floor has become so tainted by the treasure chest and the namesake that people don’t pay attention to the hurt and the pain that people have to go through paying all these extra taxes, the teachers’ pension is in jeopardy, the Chicago Police Department's pension is in jeopardy, and all these things that’s going on that’s hurting the average family. When are you gonna get your hero that’s not going to have that name recognition but that’s going to have the solution, and the people are going to honestly say, ‘I support this person?’ You know that’s a long shot.”

Armchair campaign managers and wannabe mayors have begun to map out the process to election: conduct an early poll of likely voters, build an operation by supporting a viable candidate during the 2018 governor’s campaign, then snap that organization into place before November 2018. Nomination petitions for the municipal election will go out in August 2018 and would be due in October, so voters will likely know who is running for mayor before we know the next governor.

Some of those potential challengers we heard include: City Treasurer Kurt Summers, Cook County Sheriff Tom Dart, Board of Review Commissioner Larry Rogers, Jr., Cook County Commissioner Bridget Gainer, and Cook County Commissioner Richard Boykin. Some mentioned a hope that Cook County President Toni Preckwinkle would run, but expected she would not. Others said her best opportunity was in 2015, before she increased the county sales tax by one percent making it the highest in the nation and imposed a controversial tax on sweetened beverages.  

It was the same story for Comm. Jesus “Chuy” Garcia. Several said he’d have a name recognition, but that he would need to start courting voters in predominantly black wards that went for Emanuel. Other names mentioned less frequently included: Ald. Brendan Reilly (42), Ald. Ameya Pawar (47), State Rep. LaShawn Ford, President of the Chicago Principals and Administrators Association Troy LaRaviere and Cong. Mike Quigley.  

More than most of the challengers listed, people said they are awaiting a sign from Treasurer Summers that he’s willing to challenge Emanuel directly.

As one aldermanic staffer explained, “He has been getting his name out there, but not sure if it is for mayor. Usually we see a treasurer who stays in his office, but he’s all over the place. He came here to do outreach, his office calls us regularly, they’ll come out to block parties. I can’t think of another treasurer who did that. He’s clearly trying to build a rapport.”

“I think that he’s [Summers] so tied into the political system and the machine that he won’t have the courage to challenge them. He’ll go along with the status quo. If he had the courage to step out and challenge him, I think that would be the worst nightmare ever to happen to the mayor,” said Rev. Corey Brooks.

“I’ve heard of the Treasurer wanting to be mayor, but he won’t run against Rahm. I don’t think it would happen because the fundraising mechanism comes from the same circle,” said Frank Bass.

Across Chicago, but especially in the Black community, leaders The Daily Line interviewed had heard about Summer’s Fund 77 investment program, a plan passed as part of the 2017 budget that appoints a board chaired by Summers that would invest $100 million over three years in disadvantaged neighborhoods. There’s high hopes for the program, but community leaders are not quite sure how it will help them.

“I’m always advocating for more resources and advocacy training so we can improve our corridor, said Frankye Payne, Executive Director of the Southwest Chicago Chamber of Commerce. “The Treasurer and his 77 neighborhoods plan could bring the cash flow to spur some of those things.”

The ability to secure funding could also be a deterrent. The state’s campaign finance laws are easy to work around, as was seen in 2015 when Mayor Emanuel busted the contribution caps with a $110,000 contribution from Chicago Forward, and again in 2016, when Leslie Munger accepted a $260,000 loan from her husband. Many of our sources said Mayor Emanuel’s ability to fundraise millions to spend on expensive TV spots could intimidate challengers at the grassroots level.

There’s also a great deal of doubt that Sheriff Dart will actually throw his hat into the ring in 2019. A media darling, whose jailhouse innovations have been the subject of 60 Minutes and The New York Times, Dart taunted political watchers in 2010 with public hemming and hawing about running for Mayor in 2011, with precinct captains reportedly passing his nomination petitions, but he pulled out before the filing deadline arrived. Many community leaders wonder, if he didn’t run in 2011 when it was a wide open seat, why would he run a contested campaign against a seasoned incumbent like Rahm Emanuel?

“Dart has deputies in every part of the city of all different races and ethnicities, he’s got a natural feeling for each community,” explained one aldermanic campaign manager on the southwest side. “He would probably be a good favorite. And he is based on the Southwest Side, a strong voting base.”

Cook County Board of Review Comm. Larry Rogers, Jr. has a number of interesting vectors for a candidacy. His father, Larry Rogers, Sr., is one of the city’s most successful trial attorneys and a leading advocate for African Americans in the legal profession. Rogers, Jr., who is also a trial attorney, was helped into office by then-Cong. Jesse Jackson, Jr. and never lost touch with the city’s progressive African American leaders. He has also acted as a mediator between Black leaders, as a host of a semi-regular Saturday morning gathering of the black Chicago elected officials. With his own and his father’s ties to the trial attorney community as well as his experience raising money from real estate attorneys, Rogers, Jr. would be a strong fundraiser from the start of any campaign.

The way in which Trump was elected has also gotten people to think differently: There’s no real mold any more, our sources said. And if you’re well-funded, the doors are wide open.

“I think there’s a huge opportunity for a person like Willie Wilson. Trump changed the rules. Period. While racism was at the core of electing Trump, part of that was there 30% of Latinos and 30% of Black men voted for Trump. You have the possibility of a populist,” posited South Shore activist Anton Seals, Jr. “There’s an opportunity for people that no longer have to go through the kiss-the-ring hierarchy. It will be really interesting to see.”

“I think the federal election showed us that people are really nervous and cynical of the role of big money in politics and the big money people’s role in making decisions and being the puppet masters. I could see that hurting Rahm,” said Jennifer Ritter. “People are seeing that on the state level with Ken Griffin from Citadel handpicking [Gov. Bruce] Rauner and then Rauner doing his dirty work. I think people see that with Rahm, and it could be a major vote against him.”

However, with more than two years to go to Election Day, anything could happen, and any candidate could arise. But this is Chicago, and we tend to like politicians we’ve seen before. Rev. Jedidiah Brown says his friend, comedian Michael Colyer, once complained Chicago has trouble with change. “We can’t find that person because we kill anyone who is new and organic. So whoever we pick is the same as usual.”