On a cold February day, Deidre Baumann walks down a quiet residential block in the Austin neighborhood on Chicago’s West Side with a stack of campaign postcards in one hand and her leather purse filled with buttons in the other.

She greets each passerby with a friendly but nervous smile, reminding them to vote for her in the upcoming primary election. At the behest of one resident, she pins a button onto his jacket with her name and fresh new slogan printed across: The Voice For Equal Justice.

Baumann, 55, says she has door-knocked at least 100 times over her more than a decade long effort to become a Cook County judge.

She carefully guides me around the block, introducing me to residents who are conveniently home and, coincidentally, her supporters. To many in the area, Baumann is familiar. In recent years, the West Side has become the focus of her judicial campaigns and her pro bono legal work. One resident, Shirley Fields, tells me she’s supporting Baumann because of her work in the community.

“I know that she works for our community, I know that she doesn’t live far from me, I know that her best interests is for us, and I know she did some things with the situation with the burial sites—”

“Burr Oaks,” Baumann interjects, referring to the 2009 Burr Oak Cemetery scandal when investigators learned employees at the historically Black cemetery in the southwest suburbs were digging up graves and dumping the remains to resell the plots. A civil rights and personal injury attorney, Baumann filed one of several class action lawsuits representing the families of loved ones buried at the cemetery.

Another longtime Austin resident and supporter, 91-year-old Shirley Wilson, tells me Baumann showed up for residents when massive floods hit the West Side last summer. Baumann filed a Freedom of Information Act request with local and state agencies and pushed for answers about why neighborhoods such as Austin were hit harder than any other part of the city.

“She was behind everybody to help get things done over here,” Wilson explains. “That’s how I first met her.”

After spending almost half a million dollars of her own money in five unsuccessful judicial races, Baumann says she feels like her chances of finally winning a seat on the Cook County Circuit Court are stronger than ever. Last year, she moved to Forest Park, thinking her work on the West Side would give her a leg up in the 7th Subcircuit.

But with an opponent who is already a Cook County judge after being appointed to the vacancy by the Illinois Supreme Court last year and a Black man in a subcircuit drawn to be majority Black, Baumann is facing headwinds she may not have anticipated.

Baumann tells me she’ll give up her long sought-after dream of becoming a judge if she loses the March 19 primary, her sixth run in 14 years.

“It’s been a long journey,” Baumann says with a deep sigh. “But enough is enough.”

Baumann’s repeated efforts to get on the bench as a political outsider are not uncommon in Cook County. In fact, she represents a slew of judicial candidates who — often after failing to win the support of the Cook County Democratic Party — run multiple times just to get their name out there. Among the 61 circuit court candidates this year, eight have run at least twice before. That includes her current opponent, Judge Owens J. Shelby, who ran for judge three times before he was appointed to the bench.

“Everybody has to run two or three times at best,” said judicial politics observer Jack Leyhane, who writes a blog about the topic and ran unsuccessfully for Cook County judge in 1994 and 1996. “If you’re not the endorsed candidate of the Cook County Democratic Party, you have to build your brand with the electorate in some way, and one of the ways you can do that is by being on the ballot.”

But Baumann stands out for the number of times she’s run for judge and the exorbitant amount of money she’s spent over the years. She says it’s her “calling” to become a judge. She also admits after many unsuccessful attempts at becoming the party’s slated candidate, she feels pressure to prove candidates can win independently, without the party’s support.

“My family always said, ‘If you want to be a judge, you have to kiss the ring,’” Baumann says. “And I just thought no. With my qualifications, my experience, my work — I can do it, and I will do it.”

‘Everybody wants to be a judge, but only the chosen ones become judge’

Baumann grew up in Rogers Park and says she wanted to be a lawyer from a young age. She attended law school at the University of Illinois at Urbana-Champaign and was admitted to the bar in 1992. Her first job out of law school was as an intern in the Cook County Public Defender’s Office. A year later, she joined a small law firm where she primarily handled First Amendment cases. In 1996, she opened her own practice, where she litigates personal injury, civil rights, criminal defense, and employment discrimination cases.

Throughout her time practicing in Cook County, Baumann says she witnessed clients being treated unfairly by judges who seemingly lacked empathy for her clients. So in 2010, she ran for judge in a countywide race — without a clue about what it took to run for office.

“I talked to a judge who was very supportive and encouraged me and made me feel like I could do this if I wanted to,” Baumann recalls. “But I was just learning the process at the time. I didn’t know anything about the candidate I was running against.”

Her opponents were Judge William H. Hooks, who was already a sitting judge and the Democratic Party’s slated candidate, and now-Judge William Burnett Raines, who would get elected to the bench in 2014. She placed second behind Hooks with 26% of the vote.

Baumann ran again in 2012 with a much better understanding of the political landscape. To get the support of the Cook County Democratic Party, she learned she would have to present her credentials before the party’s slating committee and promise not to run against their slated candidate if she wasn’t endorsed. She spoke at endorsement panels, appeared on cable TV, and met with the party’s high-ranking officials. She recalls meeting then-powerful 14th Ward Chicago Ald. Ed Burke, who was convicted on federal corruption charges last year.

“I talked with him once or twice, and I remember he was like, ‘Oh, yes, everybody wants to be a judge, but only the chosen ones become judge,” Baumann recalls.

She didn’t get slated but ran against the party’s candidate anyway, virtually ensuring she wouldn’t get the party’s endorsement in the future. She placed fourth in a seven-way race, losing to the slated candidate, Pamela Leeming, with only 7% of the vote.

Feeling defeated, she skipped the next election cycle. By 2016, she had assembled a team of campaign workers, including veteran political consultant Wallace “Gator” Bradley and Roman Morrow. She continued asking for the party’s endorsement, mostly “out of respect,” she says.

That year, she lost again — but so did the party’s candidate. Now-Judge Susana Ortiz, a criminal defense attorney, defeated slated candidate Pat Heneghan, while Baumann came in third with just under 16% of the vote. Heneghan was selected as an associate judge finalist days after his loss. Baumann skipped the following election cycle.

During that time, big changes were underway within the Cook County Democratic Party. Old-school machine politics were waning, giving way to a new party chair — Cook County Board President Toni Preckwinkle, who vowed to “reject politics as usual” and increase diversity among the party’s slated candidates.

In 2020, Baumann, a Jewish woman who also identifies as a member of the LGBTQ+ community, thought she finally had a chance to get slated. But after running three times against slated candidates, she still didn’t get the party’s endorsement.

She ran anyway, this time with significantly more money after securing a $1 million verdict for her client in an employment discrimination case against Chicago Public Schools. After spending less than $100,000 on her first three races combined, she spent more than $210,000 on the 2020 race, nearly all of it self-funded.

Her bar ratings, however, were consistently a problem. That year, the Chicago Bar Association did not recommend her for judge, saying “significant concerns were raised about her professionalism, diligence, and organizational skills.”

She lost to the party’s slated candidate, now-Judge Maura McMahon Zeller. Her percentage of the vote, however, jumped to 32%.

She decided to give it another shot in 2022, when she ran against the party’s slated candidate, now-Judge Michael Weaver, and prosecutor Paul Joyce. Again, the Chicago Bar Association did not recommend her for judge because of concerns with her professionalism. The Illinois State Bar Association also found her not qualified, citing concerns about her “lack of punctuality and diligence at times.”

She placed second behind Weaver, again with 32% of the vote. After losing a fifth time in a countywide race, Baumann says her team decided to take a different approach for the 2024 primary elections.

Who’s able to best serve the community?

In 1992, the state Legislature divided Cook County into 15 judicial subcircuits, with the goal of increasing diversity on the bench by electing judges from different parts of Chicago and its suburbs. In 2022, the Legislature redrew the subcircuits for the first time and added five new judicial districts.

In recent years, Baumann lived in the 9th Subcircuit, which includes Rogers Park, Evanston, Skokie, and Wilmette — an area that’s historically been friendly to Jewish candidates.

“Everyone’s always said, ‘You should run in the 9th Subcircuit,’” Baumann said. “But when I was up there, I did not get the support of that community — of my community.”

So Baumann moved to Forest Park last year, thinking she had a better chance of winning a seat in the 7th Subcircuit, a majority-Black district encompassing a large swath of Chicago’s West Side and several western suburbs.

She also says she moved with the impression she had the support of local alderpeople — Ald. Chris Taliaferro (29th Ward), Ald. Jason Ervin (28th Ward), and Ald. Emma Mitts (37th Ward).

“I don’t know where she got that from,” said Ervin, who is also the Democratic committeperson for his ward. “I’ve never ever had an endorsement conversation about Deidre Baumann in the 7th Subcircuit. When she ran countywide, it was a different conversation. But the subcircuits were specifically designed for local representation.”

Taliaferro told me he wasn’t supporting Baumann this time around and wasn’t aware she had moved into the 7th Subcircuit. Mitts did not respond to requests for comment.

Her move to the 7th Subcircuit pitted her against Shelby, a former Cook County assistant state’s attorney who is also no stranger to judicial elections. Shelby, who was born and raised on the West Side, ran unsuccessfully in the 7th Subcircuit in 2014, 2020, and 2022, before the Illinois Supreme Court appointed him to a vacancy in 2023.

When the state Legislature redrew the subcircuit boundaries for the 2024 election, Shelby’s home in Berwyn was drawn into the 3rd Subcircuit. In August, he moved to Forest Park to run in the 7th Subcircuit again. “The 7th is where I was born, grew up, my kids go to school in the 7th, I volunteer in the 7th, and pretty much my whole life has been in the 7th,” he told Injustice Watch. “It made sense to stay home.”

Facing a Black candidate in a predominantly Black subcircuit she only recently moved into, Baumann has been forced to confront questions about her motivations and why Black voters should vote for her.

At a late February candidate forum hosted by the Chicago Westside Branch of the NAACP, Baumann and Shelby sat side by side at the Columbus Park field house in Austin, facing a half-empty room.

The candidates remained cordial through the first half of the forum, answering questions about their qualifications and ability to rule impartially from the bench. But the debate grew tense when a member of the audience asked Baumann to explain why she told a radio talk show host two days earlier “Black people prefer a white judge.”

“I did not say anything to that effect,” Baumann replied. “What I said was that race was not the question here. It’s who’s best able to serve the community.”

Audio from the Feb. 26 segment of WVON’s “On the Case” show posted on Baumann’s Facebook page shows she said, “It’s critically important that our bench be diversified, but that doesn’t mean that because someone is Black they are better suited as a judge. I’ve heard stories that some criminal defendants — the last person they would want to go in front of is an African American male.”

Shelby jumped on the criticism, saying he had heard the radio interview, too. “I think it’s sad when candidates move from one community to another after running to try to find out where they think they can win,” he added.

Baumann accused Shelby of using his political connections to land a judicial appointment.

“It upsets me to hear someone say that I got appointed because of political connections,” Shelby responded. “Clearly, that person isn’t from this community or don’t know this community because everyone in this community knows that 10 years ago, I didn’t have an endorsement to my name. I walked from Walgreens to Walgreens by myself, with my wife, getting signatures.”

The Cook County Democratic Party doesn’t make endorsements in subcircuit races, but Shelby has the backing of high-ranking party members, including Cook County Clerk Karen Yarbrough and U.S. Rep. Danny Davis. Since January, Shelby’s campaign has received more than $68,000 from the committee of Illinois House of Representatives Speaker Emanuel “Chris” Welch.

Baumann, for her part, has been endorsed by 27th Ward Ald. Walter Burnett Jr. and former Illinois Secretary of State Jesse White.

“We try not to endorse people based on race, we try to endorse people based on substance,” Burnett told me. “She does a lot of pro bono work in the community.”

After the forum, Shelby shook hands and chatted with attendees. He looked comfortable and in his element, having spent years on the board of the NAACP West Side chapter. Baumann sat off to the side by herself, looking worried and distressed.

“I certainly expected that those questions would be asked, given the tenor of this campaign,” Baumann tells me later, reflecting on the forum. “The idea that I cannot represent the community simply because of my race is hurtful given my commitment to the community over a long period of time.”

What do voters really think?

A couple of weeks after walking through the Austin neighborhood with Baumann, I decide to return, this time unaccompanied by any candidate or their supporters. Some residents tell me they’re unsure about which candidate to vote for and others aren’t aware an election is coming up.

57-year-old Al Ruffin, who has lived in the neighborhood since he was a kid, has one of Baumann’s signs in his front yard.

“I talked to her a couple weeks ago, and she seemed like a really nice lady,” he tells me, saying he met her at a community meeting at his church. “I think she’s well qualified. They were asking her questions at the meeting, and she held her ground real good.”

He says race isn’t a factor in his decision, and that he looks for candidates who are fair and honest. He also says he wasn’t aware Baumann has already run five times for Cook County judge unsuccessfully. “I wonder why that is,” he says. “Now I gotta do some digging and see what’s going on.”

Another longtime resident, 81-year-old Mary Dowling, says she knew about the upcoming primary election but wasn’t sure yet who she was going to vote for. The only white person I spoke with in Austin, Dowling says race is an important factor in her decision because of the young people in her community whose “whole life can be changed by a judge — I’ve seen it happen.”

She says she looks for judicial candidates with experience and positive bar association ratings.

“I’m going to download the recommendations,” Dowling says.

A couple of houses down, Shekinah Woodard tells me she didn’t know about the March primary or either of the judicial candidates. Like Ruffin, she says a candidate’s skin color doesn’t matter much to her, but she prefers candidates who are originally from the area and can speak to the issues that matter most to her community.

I also go back to Wilson, one of Baumann’s most passionate supporters, who had told me earlier about the floods last summer. She tells me she isn’t bothered by the fact that this is Baumann’s sixth time running for judge — in fact, it strengthened her support.

“That’s what I like about her,” Wilson says. “She’s hanging in there.”

Senior reporter Maya Dukmasova contributed reporting.

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