Credit: Maya Dukmasova

The 20th Ward of Chicago stands at a historic moment. It’s on the verge of tying with the 23rd and 31st wards, both of which have had three aldermen go to prison since 1972, for the unprestigious distinction of most aldermen convicted for corruption. Its current alderman, self-described “gangster” Willie Cochran, awaits a federal trial on bribery, extortion, and wire fraud charges. Over the last 30 years two of his three predecessors—Cliff Kelley and Arenda Troutman—have gone to prison for bribery and fraud.

It’s no surprise that constituents of the ward, which encompasses much of Woodlawn and stretches west into parts of Washington Park, Englewood, and Back of the Yards, are clamoring for new leadership. Cochran isn’t seeking reelection, and by the end of November, 15 candidates had filed to run for alderman—more than in any other ward. Among them are 20th Ward Democratic committeeman Kevin Bailey, 31, and activist preacher Andre Smith, 50, both of whom ran for alderman against Cochran in prior elections. Newcomers include Chicago Police Department officer and nonprofit founder Jennifer Maddox, 47; entrepreneur and consultant Anthony Driver, 25; Chicago Housing Authority project manager Maya Hodari, 50; consultant and former CPS teacher Nicole Johnson, 29; pastor Dernard Newell, 53; and community organizer Jeanette Taylor, 43, who’s garnered union support.

As the February 26 election draws near, some in the ward already fear that their next alderman will face the same fate as his or her corrupt predecessors, but many are also hopeful that from the overcrowded field will emerge a leader with integrity who’ll focus on remedying the socioeconomic inequities that have plagued the ward for years. Foremost on residents’ minds are the high unemployment and crime rates, underresourced schools, the lack of mental health care options and affordable housing, and the challenge of balancing the development forces spearheaded by the University of Chicago and the incoming Obama Presidential Center with the needs of deeply rooted local communities. Long-term residents are wary of repeats of the Cochran-backed expansion of the Norfolk Southern rail yard, which displaced hundreds of homeowners in the ward and whose devastation was the subject of the recent documentary The Area.

Of course, getting on the ballot is the first battle. Every candidate needs at least 473 registered voters to sign their nominating petition. Each signatory must live in the ward and not have signed for any other candidate. In the 20th Ward, which contained nearly 24,000 registered voters as of last November’s election, it is mathematically possible for 15 candidates to have gathered 473 unique signatures each. However, it’s almost certain that some of the signatures filed by candidates this year are fake, forged, or duplicated. Together the aldermanic hopefuls submitted more than 30,000 signatures to the Board of Elections.

Seasoned politicos—or those who have hired seasoned consultants—often devote significant resources to challenging their opponents’ paperwork and nominating petition signatures.

In the 20th, Bailey and Johnson were the only candidates who filed objections against their competitors. Bailey challenged everyone except for Smith; Johnson, who’s out-fund-raised everyone running in the ward thus far, challenged Hodari, Maddox, and a pair of lower-profile women contenders. Candidates who face multiple objections have to battle each of them separately.

Bailey, a tall man with an athletic build, a crop of short dreads, a goatee, and a habit of reminding people that he’s a civil engineer, has been a near daily presence over the last several weeks in two large basement rooms of the Cook County office building at 69 W. Washington. This is where petition challenge hearings are held, at plastic folding tables set up in pairs around the perimeter under harsh fluorescent lights. A hearing officer, stenographer, and clerk sit on one side of a table, the candidates, their attorneys, and the people filing objections take their seats on the other. Hearings happen all week, even on weekends, as the board rushes to finalize the list of candidates to be printed on the ballot by January 21. Unlike the candidates he’s challenging, Bailey doesn’t have a lawyer but sometimes shows up to the hearings with a staffer from his campaign and his stepfather, a veteran political operator with a reputation for less-than-scrupulous campaign strategies (more on that later).

“Kevin’s mom and dad are gonna run the office if he wins.” —Anthony Driver

Bailey’s challenges are more ax than scalpel, and one hearing officer after another is finding that they aren’t made in good faith. When people file objections to petition signatures they have to file “appendix recapitulation” sheets—essentially mirrors of a candidate’s petition signature page in which objectors indicate which signatures they’re objecting to and on what grounds: that the signer isn’t registered at the address indicated, that the address isn’t in the ward, that the signature isn’t genuine, or that the signer signed another candidate’s petition first.

The Board of Elections tries to discourage “shotgun objections,” when someone indiscriminately challenges sheet upon sheet of a candidate’s signatures as faulty without the due diligence of consulting the board’s registered voter rolls. The charge must come from the candidate, but if a board hearing officer agrees that objections aren’t made in good faith they’ll recommend that the objections be dismissed and the candidate be allowed on the ballot.

Accusations that Bailey was filing shotgun objections began flying from other candidates’ camps right away. Some hearing officers have so far agreed with the candidates he’s challenged.

Twentieth Ward aldermanic candidate and Democratic committeeman Kevin Bailey (pink shirt) with his assistant Marlon Watson. The man with the mustache is Michael Dorf, an election lawyer who represents Jennifer Maddox, also running for alderman in the ward. They’re all waiting for the beginning of a hearing at the Board of Elections during which the hearing officer will decide whether Bailey’s objections to Maddox’s petitions will stand.Credit: Maya Dukmasova

Why would a candidate or his or her proxies waste time making shotgun objections if they likely won’t stand? Because that’s time lost for opponents, too. Objections, no matter how flimsy, can take days or weeks to resolve. When they aren’t shotgun objections and are allowed to move forward they involve hours of excruciating, line-by-line examinations of each signature by board staff who hole up in stuffy rooms on the sixth floor of 69 W. Washington. Candidates and their challengers, who flank the board examiner working a computer during the process, either have to spend their own time haggling over whether the signatures should count or hire people to do it for them. If disputes come down to whether a signature is genuine the board has to schedule special examinations with a handwriting expert. This process drains time and money from the opponents’ campaigns, especially if they hire lawyers to help them survive the challenge, as most of Bailey’s competitors have. Challenged candidates can’t securely campaign and raise funds while an objection is pending—it haunts them with the threat of not making it onto the ballot.

As a five-minute hearing dismissing Bailey’s objections to Jennifer Maddox’s petitions wrapped up on December 19, Bailey calmly listened to the hearing officer’s findings in his opponent’s favor. He had objected to every one of Maddox’s 1,700 signatures, and his appendix recapitulation sheets showed clear evidence of objections made without due diligence—in many cases he or his staff had marked objections to blank lines on Maddox’s petitions first (for example, 20 objections on multiple grounds on a sheet with just four signatures), then scribbled out the number of objections to match the total number of signatures on her sheet.

Nevertheless, Bailey’s objection cost Maddox a solid 16 days of Board of Elections hassles and several thousand dollars to election lawyer Michael Dorf. Bailey had also already filed a motion with the Board challenging the hearing officer’s recommendations to dismiss his objections—something that didn’t get resolved in his favor but further foiled Maddox’s campaign.

As hearing officer David Shestokas—himself a two-time candidate for Congress and a retired prosecutor—dryly explained that he was approving Dorf’s motion to strike and dismiss the objection, Bailey attempted to argue that Shestokas was wrong.

“We’re not taking any evidence,” Shestokas said.

“So there’s no discussion on the recommendation?” Bailey asked tentatively, his lips curling into a sheepish smile. When he doesn’t get his way Bailey doesn’t get mad or raise his voice but does appear ever-ready to deliver an even-toned, often tedious defense of his position if given a chance to make it.

“No sir,” Shestokas answered. Still, he allowed Bailey a moment to speak, which he used to hold forth about the hearing officer’s “inconsistent” and “not proper” decision.

“Every mistake that was pointed out [in my objection] was considered to be in bad faith and I don’t believe those were examples of bad faith,” Bailey said. “I believe objecting to those blank lines makes all the sense in the world,” he continued, making the mind-bending argument that he had no way of knowing that Maddox wouldn’t somehow try to claim the blank lines had signatures on them.

Dorf propped his white-haired, white-mustachioed head on his hand as he waited for Bailey to complete his statements. A veteran election attorney who represented Barack Obama in his early runs for public office, Dorf, with his genteel three-piece suit and bow tie, gave the impression of someone who had seen it all over the years. In an interview a few days prior, Dorf had calmly described Bailey’s challenge as “fraudulent” but a well-known machine tactic.

Dorf had no doubt that Shestokas would decide in Maddox’s favor. He handled the hearings on his own, leaving his client, the candidate, to campaign. After the hearing I asked Bailey why he wasn’t also working with a lawyer, preferring instead to waste his own campaign time hiking to the Board offices nearly every day and sitting through hearings that may last over an hour.

“I don’t think a lawyer is super necessary at this point,” he began, “but when I believe it is, a lawyer will be used.” Bailey suggested that hearing officers are biased against pro se objectors like himself and that a cliquish “culture of civility” among the legal experts wheeling and dealing in these basement rooms puts him at a disadvantage. Yet his apparent disinterest in legal representation may be an indication of his actual motivation in filing objections: not necessarily to win a legal battle but to exhaust his competition into throwing in the towel on their campaigns.

That’s certainly how Bailey’s opponents and their representatives see his copious challenges. And many have more biting things to say about him than Dorf does.

“Kevin is a scumbag,” said Anthony Driver, the entrepreneur and consultant who’s also the youngest person running for alderman in the 20th Ward. “Kevin’s mom and dad are gonna run the office if he wins.” Driver, a Back of the Yards native, has focused on registering voters and building up support in the western part of the ward he says has long been ignored by local power brokers. Bailey had initially challenged him, but abruptly withdrew his objection midway through the first evidentiary hearing. Driver says he had discovered evidence of fraud in Bailey’s filings with the Board and Bailey withdrew his objection to avoid including it in the official record. (Bailey didn’t respond when I asked him why he’d withdrawn the objection.)

But while the procedural dramas unfold in the bowels of the Election Board, the reality on the ground is that Bailey is a front-runner aldermanic candidate in the 20th despite various allegations of impropriety.

Bailey’s campaign signs are plastered on many vacant and boarded up buildings and his political organization, the Democratic committee, has grown in strength over the last two years to include the majority of election judges serving across the ward’s 39 precincts. This is due in part to the fact that his mother, Maria Bailey (who also serves as a notary and petition circulator for his campaign), was elected the Republican committee person back in the spring of 2016, at the same time Bailey became Democratic committeeman.

Party committee people in Chicago used to rule the roost in the wards as the field marshals of the machine, commanding armies of precinct captains and keeping smoothly running patronage networks well-oiled. Though their power and influence have significantly eroded since the 1980s—as has the machine itself—their most important function remains appointing election judges. Each polling place is supposed to retain both Republican and Democratic judges, although they’re not there to represent any candidates. Having both parties represented is supposed to ensure against electioneering—which is strictly forbidden with 100 feet of polling places.

This is why Cook County Republicans raised a fuss about Maria Bailey becoming ward committee person. There was speculation that she and several other committee people in Chicago were Democratic interlopers trying to consolidate power in a city with an already meager GOP presence. As evidence they cited the fact that Maria Bailey had never pulled a Republican ticket in a primary and had displayed a J.B. Pritzker lawn sign in front of her home in the run-up to the gubernatorial primary.

The Baileys have rebuffed allegations of impropriety by arguing that party doesn’t really matter in a ward. “At this level of politics I don’t believe there’s any disagreement between any party,” Kevin Bailey told me.

But concerns about the integrity of an aldermanic election in which judges appointed by the Baileys are overseeing polling places where Bailey is on the ballot have cropped up around the ward. Since the Baileys took over both major party committees, people who’d served as election judges for years began reporting improper treatment by the mother and son team.

The Reader heard about six such instances, and spoke with two election judges who both claimed one or both of the Baileys told them that they wouldn’t appoint them to serve as judges unless they agreed to work as circulators for Kevin Bailey’s campaign. One of the judges, Quintin Jones, filed a police report and a complaint with the Board of Elections last fall.

“I thought it was a joke,” Jones, 55, told me on the phone. He’d worked the same precinct in the 20th Ward as a Democratic judge for 15 years and had never been asked to do political work in exchange for his job. (Election judges get paid between $120 and $220 by the board for each day they run a polling place.)

Jones said he asked whether he’d be paid for circulating and was told that he wouldn’t be. “I refused and they removed me,” Jones said. Ultimately, he did get an election judge assignment from the Board again, but in the 3rd Ward. He said the whole thing felt like an affront to democracy. “It’s like they’re sabotaging all the judges, saying they have to be with [Bailey], for him, or we can’t work in the 20th Ward,” he said, adding that he’s worried about how Bailey’s appointed judges might behave at the polls if they’re there as repayment for campaign work.

“I think they need to be recused from this election. They shouldn’t have to tell you who they’re supporting to be able to serve,” he said. “Unfortunately the 20th Ward has not been good with aldermen, and if [Bailey’s] starting off like this, him and his mother, it’s gonna be an office of corruption. They’re already telling you they’re willing to do things . . . to benefit them regardless of whether it’s ethical or unethical.”

65 percent of the ward’s 150 judges were Kevin and Maria Bailey’s appointees. Many of them were serving for the first time.

Board records obtained by the Reader show that in last November’s election, 65 percent of the ward’s 150 judges were Kevin and Maria Bailey’s appointees. Many of them were serving for the first time.

Collean Fuller, 86, has been a precinct captain in the 20th Ward for decades. She says she’s noticed a big turnover in election judges since the Baileys took over. When she went to vote last November, she said all the the people working her polling place were new and “didn’t know bullfrog from catfish. Some of them were asking for your social security card, some of them were asking for your driver’s license.”

Fuller said the ballot counting machine was also malfunctioning and they didn’t know how to fix it. “I went to vote and the machine pushed me out three times,” she said. In the end she said she walked out exasperated, not sure whether her vote even counted. “I said, ‘I know who I am, where I stand, I know who I serve, so fuck it.'”

Fuller apologized for being crude and added that she went to to Bailey’s office at 63rd and St. Lawrence to complain about the machine but was told that the committeeman wasn’t there. “He was riding around with  J.B. on election day,” she said, with a note of indignation. (Pritzker has donated $10,000 to Bailey’s Democratic committee, state campaign finance records show.)

Fuller didn’t want to say who she was supporting for alderman for fear of political reprisals, but she did note that she didn’t like how many of the 20th Ward candidates seemed to appear out of thin air. “The 20th Ward needs good candidates, and they need candidates who’ve lived in the ward for at least five years,” she said. “The seniors not getting theirs, the kids not getting theirs—we’re lost. We can’t get service, so we’re just out here by ourselves. And I ain’t never seen these guys until election time. I don’t even know the names.”

Fuller wasn’t alone in her skepticism. On the Saturday before Christmas, a couple dozen kids rushed a small wooden stage in the middle of a community garden plot on the 6000 block of South Vernon. They’d been brought to carol for the neighbors by Maddox’s nonprofit after school program Future Ties. As the kids wound their way through the holiday classics, wiggling and dancing, eager for their hot chocolate reward, a few passersby stopped to watch and sing along. When they were done, a man walking away with his family said “It feels good to be caroled to on some Christmases.” He paused for effect and to get the attention of the woman walking with him. “We don’t get caroled every year. Only when it’s time to vote.”

Maddox isn’t surprised by such cynicism. She said she’d probably feel the same way if she’d never met a candidate in person, and noted that the caroling wasn’t meant as a campaign event. Indeed, she hadn’t mentioned a word about the election as she led the singing dressed down in a fleece jacket and sweatpants. Neither did candidate Maya Hodari, who’d stopped by to mingle with her 11-year-old son.

“I don’t try to force no one’s hand,” Maddox explained. “I go to [voters] and explain why I’m doing what I’m doing, I give them a little background and history on myself, I ask them to google me, and I invite them to have a conversation with me afterwards to discuss moving forward with the ward.” (Googling Maddox yields a link to her CNN Heroes profile.)

Maddox hopes that her ten years of serving hundreds of kids from the Parkway Gardens low-income apartment complex with after-school and summer camp programs, mostly on her own dime, will persuade voters that she’s a person sincerely dedicated to the well-being of the community. She adds that people sometimes narrow their eyes when they discover that she’s a cop, especially given the fact that Cochran had also been a police officer. “But I explain to them all police officers aren’t the same,” she says.

Maddox sees the fact that she was challenged by both Bailey and Nicole Johnson as a sign that she’s got a good chance to win. “I do think I’m a threat to them,” she said, even without the money, party, union, or church backing some of the other candidates have. I spoke with her this week after she’d spent a grueling weekend fighting Johnson’s objections to her signatures.

“When we were going through the signatures the Board of Election [examiner] overruled a lot of the objections because clearly the people were in the ward and they were registered voters,” Maddox said. The objectors—people hired by Johnson’s camp to actually come to the Board—were “not even following along on the screen. I had four people sit with me four different times and they had their earphones in their ears, writing on their paper, and just saying: ‘Object, object.'” She said it was clear the process was meant to discourage her; if she didn’t stay vigilant and fight every objection, her valid signature count could dip below the necessary 473.

“These last three days have really drained me and I need to get myself back up and running again,” she said.

As Maddox, Hodari, Dernard Newell, Jeanette Taylor, and others trudge through the tedious procedural hurdles set up by their opponents, one of the chief contenders in the race has wasted neither his own nor other people’s time with the petition challenge process.

Operating out of a storefront office a few doors down from Cochran’s ward headquarters on Cottage Grove, Andre Smith is running a loud and visible campaign, bolstered by his advantage as a third-time candidate.

Smith has learned a lot in his previous two runs for alderman and has a campaign “war room” plastered with precinct maps in the back of his office. Dressed in a turquoise shirt and black slacks, he slammed a fat stack of papers on his desk when I asked him why he thought no one had challenged him. They were affidavits signed by every one of his petition signatories, he explained, stating that they really had signed for him first. No one would have been able to claim his signatures weren’t valid.

Twentieth Ward aldermanic candidate Andre Smith, who’s run for the seat unsuccessfully two previous times against Cochran. Here he’s showing a stack of affidavits obtained from each person he asked to sign his nominating petitions.Credit: Maya Dukmasova

“Welcome to Andre Smith,” he said with a grin as he popped open a can of soda.

In many ways Smith is already acting like an alderman. In his front office, volunteers and staff organize donations for a toy drive and take calls from residents complaining about uncut trees, unplowed streets, and criminal activity. They keep notes on follow-­up calls and whether each issue has ultimately been resolved. If the callers don’t have luck getting help from Cochran, Smith takes it upon himself to contact the ward superintendent or the city’s Streets and Sanitation department to handle potholes or broken street lights. Sometimes he’ll send his own people out to fix a resident’s problem.

Many people in the ward, and some city officials, “already treat me like I was the alderman,” he claims.

Despite a fervent base of supporters, Smith has also landed in hot water. Last fall, he was alleged to have solicited petition signatures in exchange for free Thanksgiving turkeys. Rumors persist about his campaign volunteers bullying voters. But none of that is slowing him down.

Smith has a habit of talking about himself in the third person and providing receipts for his claims. Over the course of our conversation he periodically whipped out his phone to show me videos of himself clearing brush from vacant lots with a chain saw, he dug up copies of newspaper articles citing his presence at community events, and even showed me framed report cards and certificates from a young man who he said had been a homeless high school dropout gang banging in the neighborhood before Smith gave him a job circulating his petitions and got him back into school. He proudly showed me footage of the young man fanning out a stack of hundred dollar bills on his phone.

“All legal money,” the boy could be heard saying, flashing a yellow receipt at the camera. “Real gangsters into politics.”

“This is Andre Smith over in the campaign office, helping out, giving back, taking the brothers from off the street, putting them into the political world so they can learn how to make real money,” Smith says as he turns the camera on himself in the video. “This is what we do, this is what leadership is all about.”

Smith suggested this is his year and said that no one else running has a proven track record of community service in the ward. He scoffed at the first-time candidates campaigning out of their homes and focusing on fund-raising. “These people, most of them are opportunists,” he said, jabbing his finger at a list of his opponents’ names. “We’ve been fighting Cochran for 12 years—where was you at?”

Meanwhile, on the west end of the ward, Driver may be the newest of the newcomers, but he’s developed a keen analysis of what it will take to win this election. Given that in 2015 only 6,614 people cast a vote in the election that resulted in a runoff between Cochran and Bailey—and that Cochran won the runoff by only 849 votes with a war chest ten times the size of Bailey’s—Driver said this election will come down to a “game of bases.” He believed he’d be able to get the most people out to the polls when the time came.

“The seniors not getting theirs, the kids not getting theirs—we’re lost. We can’t get service, so we’re just out here by ourselves. And I ain’t never seen these guys until election time. I don’t even know the names.” —Collean Fuller

Driver, who was a fellow in Rahm Emanuel’s Office of Public Engagement, has interned on Capitol Hill, and has been invited to the White House on multiple occasions, hopes people will see him as a viable alternative to the same-old self-serving politicians. He’s waged an issue-driven battle centered on tackling lead contamination in drinking water, creating a way for residents to drop off guns to the police anonymously 24-7, and boosting affordable housing options.

Soft-spoken and armed with what appears to be deeply researched understanding of the ward’s demographics Driver has focused his campaign on door-knocking, especially in the poorer parts of the ward where people aren’t seen as likely voters by the establishment types. Having lost two close, college-bound friends to gun violence, he says he understands the challenges locals face and that he has the right communication skills and pedigree to make their concerns matter in City Hall.

A few days before Christmas, Driver stopped at Robust Coffee Lounge on the corner of 63rd and Woodlawn dressed down in a Bulls hoodie, black beanie, and puffer coat.

“When I’m dressed like this, and I’m walking out in the neighborhood, I’m going to be mistaken for a gangbanger. I’m going to be mistaken for a criminal. No one’s gonna know I have two degrees, that I’ve studied abroad,” he said. Though he’s battling a stigma because of his youth, he adds that his age is precisely what’s helping him get through to disaffected young people who don’t see a reflection of themselves in politicians.

“I’m the only person who can go into any neighborhood in the 20th Ward—the worst neighborhoods—and speak the language, talk to people out on the street, and in the same breath turn around and call someone directly at City Hall and they’re gonna answer because of my education, because of my connections. I’m the only person who can bring those worlds together.” It helps that he comes from a family of precinct captains highly active in local politics.

Driver also admires many of the other candidates running and maintains friendly relationships with them. He thinks the fact that the majority of the candidates are trying to play fair is a good sign of the shifting political culture in the ward. On his way out of the coffee shop he ran into Hodari and exchanged commiserations about Bailey.

Hodari has been a passionate advocate for the Obama Presidential Center and wants to prioritize economic development in the community. She’s for a community benefits agreement, but says that seeing a development of national import will be a boon for local kids who only get to see their neighborhood and themselves associated with crime and poverty. She too hopes the election will yield a more vibrant civic culture in the ward.

“This is not any of our last stop,” she said, reflecting on the crowded field of candidates. “I think that this has been an opportunity to get key people who are passionate about moving things forward in the 20th Ward—now we know one another. Now we can, if we choose to, work together beyond this election.”

Back on December 19, just a few hours after Bailey’s challenge of Jennifer Maddox collapsed, he and Nicole Johnson’s attorney Andrew Finko sat before hearing officer Yamil Colon. Bailey was joined by his stepfather, Hassan Muhammad, a short, pudgy man who sat behind him and grabbed onto his shoulders to whisper intensely into his ear so frequently that Colon made him introduce himself for the record.

Muhammad is a longtime political operative on the south side who’s worked for Congressman Danny Davis and Cook County Clerk of the Circuit Court-turned-mayoral candidate Dorothy Brown. In the past, he’s been the source of controversy on campaigns. In 2009, reports surfaced that he was ordering state-funded workers who’d signed up to receive job training through his nonprofit to collect petition signatures for Brown’s run for Cook County Board president. When he was confronted about this by reporters from FOX Chicago, Muhammad appeared to snatch documents from their hands, denied any wrongdoing, and was arrested on camera, although the station didn’t ultimately press any charges.

At the hearing, Colon decided to send a sample of Bailey’s many pages of objections for examination by Board staff, which would reflect the quality of his entire objection. They’d go through 10 percent of Bailey’s appendix recapitulation sheets and decide whether he was making good-faith challenges with his 5,343 objections to Johnson’s 2,727 signatures.

“There’s a pattern that they’re looking for, OK?” Colon explained to Bailey, who began arguing that this examination wouldn’t be “holistic.”

“A pattern he’s looking for,” Muhammad mumbled loudly, jerking his head in Finko’s direction.

Colon ignored the comment and ended the hearing. But Muhammad was getting heated. “It’s subjective and arbitrary,” he grumbled. “You wanna look at part of the sheet, not the whole sheet,” he continued. “Not everything on the sheet is what I wanna look at,” he whined in a high-pitched voice, in apparent mockery of Colon.

An awkward silence descended on the people around the hearing table. “Sorry, the team has put in a lot of time and effort,” Bailey said to Colon with a smirk and a nervous laugh.

“I understand,” Colon replied. “People get frustrated and upset at these things and there’s nothing wrong with expressing your frustration.” They set a date for the next hearing.

Muhammad continued mumbling and mocking Colon. He eventually stormed out of the hearing room and, finding an audience in the hallway, escalated his complaints to a torrent of angry shouts. Finko, a veteran election lawyer with a mane of sandy hair and a gigantic silver signet ring of the Ukrainian coat of arms, scooted away with his chair to the other side of the room for a client running in a different ward.

Reflecting on Bailey’s challenge later, Finko didn’t mince words. “I think what he’s doing is an abuse of the system and an abuse of the rules,” he said. He added that Bailey’s objections were a waste of taxpayer dollars, since the board had to spend time and money on hearings that go nowhere. “I don’t mind if someone files an objection for valid reasons—that’s the rules,” he said, apparently considering his own camp’s challenges to be above board. “The stuff that Bailey is pulling—it’s not professional.”

Two days after Muhammad’s meltdown, the board found that 82 percent of Bailey’s objections didn’t stand up to scrutiny. Finko filed a motion saying that the “implications of Kevin Bailey’s actions . . . are very troubling. Residents of the 20th Ward deserve an alderman who has good moral fiber, honesty, and integrity, at all times.”

Colon wrote a recommendation to the board stating that Bailey “did not meet his burden of showing due diligence and inquiry. The objection petition appears to have been conceived in fraud, false pleading, and bad faith.”

At a meeting last week, the board adopted Colon’s recommendation and rejected Bailey’s objections. Nicole Johnson made the ballot.

Reflecting on the ordeal after a month of hearings and legal expenses, Johnson said last week that Bailey’s tactics are indicative of “the type of chicanery that we have going on, which is unfortunately in the culture of the 20th Ward.”

I asked why, given her campaign resources (she’s gotten thousands of dollars from wealthy donors connected to the University of Chicago) and her belief that Bailey isn’t playing fair, she didn’t file an objection against him and focused on trying to knock other opponents—all women—off the ballot instead. She explained it was a question of resources.

Given that Bailey filed 900 pages of petition signatures and candidates only had a week to file objections “that would have been so much energy devoted to one particular individual,” Johnson said. She and other 20th Ward candidates told me that Bailey would likely have had the 473 signatures needed to make the ballot anyway, even if more than half of those filed could have been thrown out.

Johnson, an Englewood native who’s been campaigning with plans to boost small business activity and strengthen connections between local schools and colleges, lamented the way Bailey’s shenanigans took candidates’ attention away from pressing issues in the ward. Poverty, crime, lack of educational resources, and economic disenfranchisement all went unchecked, she suggested, while local concerns that the ward’s politicians are steeped in corruption only flourished.

She said she’s come across many residents who ask, “How are you gonna make sure you don’t go to jail?” and added that any serious candidate in the 20th Ward must have a compelling answer. The way she sees it, it’s about surrounding yourself with the right advisors, being transparent, and soliciting community input when making decisions, especially about real estate and business development.

For his part, Bailey dismissed his opponents’ complaints about his tactics. He said his challenges “are all a part of challenging the status quo, increasing the quality of candidate that services our community.” He declined to explain why he didn’t challenge Smith, but talked about petition challenges almost as a civic duty, suggesting that they police candidates’ integrity and diligence in complying with the rules.

“As a person who’s pro se in this legal system I will not be the biggest challenge that whoever gets into this aldermanic office will face,” he said. “And if they can’t handle an initial fight how can they expect to excel when it comes to fighting over resources against other seasoned aldermen that know the system in and out?”

When I asked Bailey about his campaign platform, he began talking about Cochran’s inability to provide adequate basic services in the ward, such as trash cans, and claimed it’s led to the proliferation of cat-sized rats. He also talked about shootings and illegal evictions as he sat in the front area of his office, wallpapered with pictures of his face.

“The schools are still on the chopping block, some are closing down, some are getting turned around, but overall we still need need holistic investment in our kids and in their future, especially while their minds are still malleable, and uh . . . I said public safety—is that all of them?” he asked, turning towards his mother, Maria Bailey, who’d been hovering around and periodically scribbling in a notebook. “The focal points are: education, health and human services, economic development,” Bailey said, counting off his fingers. “I’m missing one . . .”

“I don’t know, you were in the middle of a meeting back here,” Maria Bailey said with a chuckle. She appeared to be growing impatient that her son was dawdling with a reporter while office staff were feverishly completing paperwork for yet another challenge-related filing deadline.

But Bailey wanted to finish his thought. “Health and human services, public safety, education, economic development—yeah that’s it, those were the four,” he finally concluded, satisfied. These would be the central subjects of his campaign, just as they were the last time he ran and since he’d become committeeman, Bailey said.

“There’s not gonna be a change in the focus” of his campaign, he explained. As allegations of bad faith and corruption swirl around him, he said he’s keeping his mind on how to best serve the residents because, since he’s gotten into politics, “the quality of life hasn’t improved in the community.” v

Update: Kevin Bailey’s media relations coordinator Nakita McGraw reached out to the Reader after the January 10 issue went to press  explaining that the reason Bailey withdrew his petition challenge to Driver was “because our recapitulation sheets on 3 candidates mysteriously disappeared.” She wrote that the campaign had filed “full, complete, and accurate” sets of paperwork with the Board to challenge Driver and two others, implying that parts of the filings may have disappeared while in Board custody, hindering Bailey from moving forward with his objections. She went on to say that Bailey’s campaign “subpoenad [sic] the board for video, still photos, audio from the time we drop [sic] them off until the time they took them to the sheriffs department [to serve the candidates with the challenges] . . . and the board refused to give us any of that information.”

“We’re handling 181 objections right now. There are no complaints in the other 178,” Board of Elections spokesman Jim Allen said in response to Bailey’s concerns. “We’ll gladly look into his claims but . . . the suggestion here is that sheets are missing from multiple sets of the same objections, and only objections filed from one person. I’ll let the public be the judge of that.”

Correction: Pritzker’s donation to Bailey was made in the run-up to the 2016 gubernatorial election, not last week.

Correction to the previous correction: That should of course say 2018 gubernatorial election.