By Mary L. Datcher

With the mayoral election taking place February 26, Chicago residents are not out of the woods for yet another high stakes election. The chips are stacked high as two-term mayor, Rahm Emanuel takes his final bow as in the final countdown of reliving the helm. Who will be remixing the next phase of city legislation?

Out of the 21 candidates—eight women contenders are hoping to make political history by being the first woman of color to take her seat on the fifth floor. Two of the mayoral candidates have won re-election of their current positions—Toni Preckwinkle was recently elected for a third term as the CookCounty Board President and Susana Mendoza securing a full term as Illinois State Comptroller.

Six African American women, one White and one Hispanic woman battle to become the next leader of the third largest city in the country—a city still racially and economically divided. With a significant pension deficit that is not going away as each camp fight for union endorsements; a declining population; consistent crime in underserved communities; and rising housing costs. A broken system often based on backdoor dealings and an operative pie split into uneven slices accommodating the loyal and punishing the outsiders. Will a woman of color be elected to lead the city and smooth the rough edges left behind by the male-dominated machine?

Toni Preckwinkle

Occupation: Cook County Board President

Age: 71
Positions held: History teacher, Executive Director of the Chicago Jobs Council, 4th Ward Alderman

Relationship Status: Divorced

Campaign Funds Raised: $164,178.49

Toni Preckwinkle became the first African American woman to Chair the Cook County Democratic Party—a role held mainly by white males. As the Cook County Board President, she oversees one of the largest counties in the U.S. –responsible for the healthcare, court, correctional jail systems along with the county forest preserves.

A former school teacher, Preckwinkle is a native of St. Paul, Minnesota and relocated to Chicago. Her work with several non-profit organizations eventually led her to win the 4th Ward aldermanic office—upsetting then-incumbent Alderman Tim Evans. Recently divorced, she is a mother and grandmother who spends time with her grandchildren while overseeing the largest county in the state.

“Being an elected official makes it hard to achieve that balance because of the demands on us. I used to say when I was alderman whenever we went out the door; we’re on duty. Whether you’re walking your dog or in the grocery store, people felt free to stop and talk to you, raise issues and sometimes confront you. So, you get used to very public life. It’s hard, at least for me set aside the personal and family time that balances your life. I’m grateful for my grandchildren; I make it a point to do things for them. It takes me out of my professional spirit.”

Recently endorsed by the Chicago Teachers Union (CTU), Service Employees International Union Healthcare Illinois (SEIU Local 73 and Local 1), Preckwinkle accepted a $1Mcontribution from the region’s largest labor union.

She’s had her woes with an aggressive, anti- beverage tax campaign dividing the County board. This put added pressure on allies to vote down a tax that pushed to close a $200 million deficit. Recently, Preckwinkle’s former Chief of Security was fired due to an unreported and missing county-owned SUV found in the suburbs with political literature in the trunk. According to the Chicago Tribune, the former driver of Preckwinkle saying she was aware of the Kimberly Foxx campaign literature in the trunk and he was a scapegoat. Former alderman and mayoral candidate, Bob Fioretti is calling for an investigation into the matter.

However, despite her critics and soured publicopinion—she has a well-oiled machine of loyalists and ‘bleeding Black and blue’ Dems in her corner. Her Campaign Finance Chair, Ken Bennett—a long-time political insider and former aide to then-US Senator Barack Obama and Mayor Rahm Emanuel is on board. His commitment for Preckwinkle faces off with his eldest son, Chance the Rapper’s support for Amara Enyia.

Dorothy A. Brown

Occupation: Clerk of the Circuit Court of Cook County
Age: 65
Positions held: Arthur Anderson, Commonwealth Edison, and General Auditor for Chicago Transit Authority (CTA) Relationship Status: Married

Campaigns Funds Raised: $39,764.02

Not a newbie to the mayoral race, Dorothy Brown took her first plunge in the murky waters in 2006 running against incumbent Richard M. Daley. In defeat, she maintained her current role as the Clerk of the Circuit Court of CookCounty—an office she’s served four terms. Running for Cook County Board President, she locked horns with Toni Preckwinkle running for the same office and defeated in the Democratic Primaries in 2010.

In her signature red, Brown has garnered the respect and public popularity from her constituents—winning the last election by nearly76 percent. She won without the endorsement of the Cook County Democratic party under a federal probe into alleged patronage hiring.

Not charged with any wrongdoing, the Louisiana native maintains her innocence and proudly threw her hat into the mayoral race. One of the first candidates to hit the ground running, she often overlooked and underestimated as a significant contender despite her engagement with voters. With the general media watching her every move, she is not active in the polls.

She claps back, “My vote consists of the people. Just like they were able to get the Hillary Clinton and Donald Trump wrong. I’m going to focus on the people to make sure I get the votes from the people. We feel very confident and the response we’ve been getting from people—moving around. I’m not concerned about mainstream media is doing the main thing that counts Feb.26. Make sure that people know who Dorothy Brown is and my plans,” says Brown.

Brown is confident she will get the loyal base of voters who continue to re-elect her to her county seat.
Being one of the first candidates to make herannouncement—she says she was prepared to run with Rahm Emmanuel in the race or not.

“His withdrawal habit does not change my strategy. I’m not running against Rahm Emmanuel; I’m running for the people of the city of Chicago. That’s what I’m going to continue to do. I will continue to be committed to bringing a high quality of education to every one of the children. Every community—I’m committed to bringing the economic development. I’m talking about community health and wealth building in this city of Chicago,” she says.

Currently, one of two women candidates challenged by Preckwinkle—she is determined to stay in the race. A strategy often played by candidates with the legal and financial muscle to knock down candidates off of the ballot ensuring their chances for a win. She says she’s focused on continuing her neighborhood listening tour where topics of concern continue to resonate throughout the mayoral forums.

“Everyone is concerned about the crime— every single neighborhood. Residents concerned about the lack of education and properly educating our children,” Brown points out. “Economic development—particularly jobs. I feel my campaign has the right focus. Some neighborhoods have concerns about immigration to ensure we’re a sanctuary city andI’m committed about that. Also, the DACA— the dreamers. These are the things that are a primary concern.”

Lori Lightfoot

Occupation: Attorney
Age: 56
Relationship Status: Married
Positions held: Senior equity partner, Chair of the Police Accountability Task Force, President of the Chicago Police Board, First Deputy of the Chicago Department of Procurement Services, Assistant United States Attorney Campaign Funds: $531,422.49

As the former Chair of the Police Accountability Task Force, Lori Lightfoot had one of the hardest jobs in the field of red tape bureaucracy. In the midst of an explosive court-ordered dashcam capturing then-Chicago police officer, Jason Van Dyke firing 16 shots into the 16-year-old LaQuan McDonald—it would forever change how CPD facilities police misconduct complaints. Her findings and recommendations would mirror the Department of Justice report issued in January 2017.

Lightfoot has an extensive background working as a former federal prosecutor and eventually going to work for then-Chicago Police Department Supt. Terry Hillard from 2002- 2004.

“I ran was called Office Professional Standards which had been around since the 1970s. It’s similar to IPRA and now COPA. The difference was embedded in the CPD. It made things getting things done more challenging and complicated. One of the things I emphasized there—even under OPS, the jurisdiction to investigate allegations of police misconduct and also included investigation of police-involved shootings, citizen allegations of excessive force.”

Her tenacity for analyzing cases and providing in-depth recommendations to prevent future problems would lead to eventually disagreeing with the current mayor who hired her for IPRA.

Her decision to run for mayor, at first challenging Emanuel drew gasps without fear, becoming one of the first potential mayoral candidates. Now, with Emanuel’s decision to not run for another term, Lightfoot finds herself in a pool of fellow-female candidates most likely splitting the vote among people of color and women. Lightfoot’s humble upbringing in Ohio, the daughter of parents who fled Jim Crow South, motivated her to rise above her circumstances. Earning her Bachelor of Arts degree at the University of Michigan and her law degree at the University of Chicago–she is fearless. “There are several qualities, but the main one is that I’m independent. I didn’t come up through the ward system. I’m not part of the establishment party. I’m not somebody sent; I’m here for the people of Chicago. I have a very different vision for the relationship between city government and individual citizens, and that is one based on mutual respect — one in which equity and inclusion are truly NorthStar’s. Where we sit down, and we solve problems together by putting people first. Making sure the city government—people that work for the city understand about being a public servant,” she said.

Lightfoot has a comprehensive plan laid out on her campaign. From public safety, expanding affordable housing options, police reform, cleaning up city government, protecting Chicago’s immigration reform, and legalizing marijuana. She resides on the Northside with her wife, Amy Eshleman and 10-year-old daughter.

Susana Mendoza

Occupation: State of Illinois Comptroller
Age: 46
Positions held: IL State Representative (1st District), Chicago City Clerk, Collegiate Soccer Player

Relationship Status: Married
Campaign Funds Raised: $2,023,396.52

Who is the one person that ruffled some feathers among the mayoral candidates? Yep. The 5ft 2” ball of fire which can kick a mean soccer ball down the field—Susana Mendoza. Mendoza is not a rookie in this lane, and she has chips in her purse—not potato chips—but Mendoza has that real bag.

She’s served ten years as the Illinois State Representative for the 1st District and co-founder of the Illinois Legislative Caucus. Later, Mendoza became the first woman elected to Chicago City Clerk office cutting her teeth learning the infrastructure of city government.

In 2017, Mendoza went head-to-head with Rauner-appointed Illinois Comptroller, Leslie Munger in a special election, winning the seat. Her critics have accused her of being controlled by Illinois House Speaker Michael Madigan, but she insists she is independent of the Madigan machine.

At a recent mayoral forum held at Chicago Teachers Union Headquarters, Preckwinkle challenged Mendoza on her position for the death penalty while she served as a State legislator.

She turns to Mendoza and asks, “Most of your time downstate, you were a proponent of the death penalty and said at one point you would flip the switch. Given the disproportionate impact the criminal system has on Black and brown people, how can we be confident you’ll be supportive of criminal justice reform?

Mendoza retorts back to the Democratic Cook County Chair, “Thank you for asking that question. I know what’s it like to be on the other side of crime. My tenure as a legislator was fighting to protect communities of color against violence—against people—informed by my own life’s experience,” she says. “Yes, I did support the death penalty, but I was the deciding vote to abolish the death penalty in the state of Illinois. People who look like me, Black and Brown, faces across the city feel victimize every day doing crimes against them, and that’s not okay. I’ll always stand up for families and children being victimized by gangs, and I don’t feel like families need to leave their neighborhoods as a result of that.”

From the sound of this exchange, this is just the tip of the iceberg—winter is here.

Amara Enyia

Occupation: Executive Director of Austin Chamber of Commerce
Age: 35
Positions held: Journalist, Author, Policy Consultant

Relationship Status: Single
Campaign Funds Raised: $200,067.54

Having worked in policy, Enyia understands she has her work cut out for her and feels she is up for the challenge. As she identifies the ongoing problems and tensions built up between the current administration and the Black community—drastically forcing out families and small businesses beyond the city limits—she believes it will take independent and progressive thinkers to become active.

With a healthy boost to her campaign with high-profile endorsements by Chance the Rapper and Kanye West, she has politic Gods on her side. Battling Willie ‘deep-pockets’ Wilson, she was challenged in the last mayoral election not making the ballot. This time around, her petitions were not challenged—allowing her to earn a place on the ballot.

Born Amarachuka Enyia, one of five siblings from Nigerian parents who migrated to Chicago in the 1990’s—Enyia says it was the strength and activism of her family which impacted her path in fighting for change.

“We’re offering different ideas about government that is transformative and not only that; they are durable. So, when we talk about the economy, we’re not talking about how we’re going to change the pension formula, we’re talking about how we restructure our economic system where we have a financial institution that’s sole responsibility to create a healthy economy?,” said Enyia.

With absolute confidence, “We’re diversifying our economic ecosystem to develop new pathways to ownership particularly in marginalized communities. We’re putting in mechanisms to create affordability like community land trusts, housing cooperatives. These are things we don’t do in Chicago because of the limitations of our thinking. We’re not just giving the empty talking points.”

Other Candidates

Other women candidates include Sandra Mallory, Catherine Tycoon, and Conrien Hykes Clark. With little or no track record in policy, public service or funds—it’s hard to gauge what platforms they stand for. The crowded mayoral race is not for the weary or the weak. As of September 2018, these candidates have not reported campaign fund contributions or expenditures.

Follow Mary L. Datcher on Twitter