Breaking Down the Ballot: The 2019 Chicago Municipal Elections

Toni Preckwinkle is currently the President of the Cook County Board of Commissioners, the body that performs both executive and legislative duties for the county. Preckwinkle holds a bachelors and masters degree from the University of Chicago, and resides in the Hyde Park area. She served as a high school history teacher at several schools for 10 years, and eventually challenged incumbent Alderman Tim Evans for his 4th Ward seat three times. In a razor-thin 1991 election, Preckwinkle successfully defeated the 17-year incumbent.

Preckwinkle is the oldest mayoral candidate at age 71, and was the politician who convinced Barack Obama to challenge Illinois Congressman Bobby Rush in the 2000 election.

Preckwinkle has been endorsed by the Chicago Teachers Union, Chicago Aldermen Sophia King, Leslie Hairston, and Carlos Ramirez-Rosa, and senior adviser to former President Barack Obama Valerie Jarrett. Her campaign has raised over $4 million dollars to date, with $3.4 million in cash on hand.

Preckwinkle supports a Community Benefits Agreement for the Obama Presidential Center, has called for an elected school board for the Chicago Public Schools district, and supports the abolishment of controversial Tax Increment Financing Districts that grant members of the City Council substantial authority over how millions of dollars in property taxes are invested within their wards. Her campaign supports a ban on any outside employment for alderman and other public officials in Chicago, as well as term limits on their tenure.

-Richard Omoniyi-Shoyoola

Susana Mendoza is currently the Illinois Comptroller, responsible for making payments for the fiscal accounts of the state. She is a native Chicagoan who attended Truman State University, graduating with a degree in Business Administration. Mendoza worked as a press secretary for machine Alderman Ray Frias, prior to her election as one of the youngest Illinois State Representatives at age 28, and as the first female Chicago City Clerk in 2011. Mendoza centers her campaign on violent crime, high property taxes, and improving schools She dubs these “issues [she] has dealt with [her] whole life” — as during her childhood, her family moved out of their home in Little Village to the suburb of Bolingbrook after a nearby shooting.


Mendoza supports the Consent Decree established between the Department of Justice and the Chicago Police Department to reform policing in the city. As mayor, she intends to create an ethics, accountability, and anti-corruption commission for political misconduct, and an end to aldermanic prerogative that grants Alderman nearly complete control over how and where public funds are spent in their districts—the norm has come under fire for contributing to segregation and inequities in community development.

-Richard Omoniyi-Shoyoola

Bill Daley A member of the Daley family has participated in 14 of the last 18 Chicago mayoral races, and this year’s shall be no exception. At age 70, Bill Daley is vying to add to the combined 43 years his father and brother, Richard J and M Daley, served as Chicago mayor. Through Daley has not yet held an elected office, his career has reached heights in politics, law, and banking. Daley was Commerce Secretary during Bill Clinton’s second term and White House Chief of Staff during President Barack Obama’s first term. Daley served as the president (1990-1993) of the Amalgamated Bank of Chicago. Daley earned his J.D. from John Marshall Law School (B.A. from Loyola University Chicago, and went on to become a partner in several law firms). Daley has also sat on the board of trustees of Boeing Corp, Merck & Co, Boston Properties, Loyola University Chicago and (currently) Northwestern University.

Sweeping governance reform is a key focus of Bill Daley’s policy proposals: Daley has proposed limiting Chicago mayors to two terms, and banning members of his family from doing business with the city, and shrinking the number of alderman from 50 to 15, limiting them to three terms, and prohibiting them for earning outside income.

Daley also supports a freeze on property taxes. Another Daley signature proposal is to spend $50 million on neighborhood violence prevention. Another Daley priority is sustaining the affordable housing supply through enforcement of existing ordinances and market-based solutions. On education, Daley supports expanding CPS funding and providing free community college to high-performing CPS graduates as well as scholarships to low-income students. On pensions, Daley supports benefits reforms that limit costs as well as raising alternative forms of revenue. Daley has decried “kick the can” budgeting that leads to a high portion of revenues going towards debt service.

Daley has the endorsement of US Congressman Bobby Rush (D, IL-1) as well as 2000 presidential candidate Al Gore. As of February 8th, Daley has raised $5.94 million in campaign contributions, millions more than any other candidate.

-David Whyman

Amara Enyia After a fellowship in the offices of then-Mayor Richard M. Daley, Amara Enyia turned to community organizing in the South and West Sides. Although she has never held public office, she is running to return to City Hall, this time, as mayor. Enyia is currently the President of the Austin Chamber of Commerce. Enyia also worked as a civic consultant, founding consulting firm ACE Municipal Partners. Enyia also served as executive director of Austin Coming Together, which launched a neighborhood community development corporation. At the University of Illinois at Urbana-Champaign, Enyia earned her J.D., her Masters degree in education, and her PhD in Education Policy. Enyia is fluent in five languages including Igbo, the native language of her parents, who immigrated to the US from Nigeria before her birth.

Enyia’s issues platform includes a list of economic justice and governance reform proposals. Institutional changes include the creation of a public bank and the switch to an elected school board. On education, Enyia supports increased CPS funding. In addition to greater transparency and citizen input, governance reform proposals strengthening the oversight and investigative powers of the Inspector General, preventing alderman from earning side income, and shifting neighborhood executive functions from alderman to city departments under the mayor’s purview. On the economic side, she supports increased use of community benefits agreements. Enyia also prioritizes investment in public transportation as well as tinkering with city fines and ticketing with an eye to their impact on low-income Chicagoans. Enyia has also proposed reopening mental health facilities that the city had previously disbanded. On budgeting, Enyia has committed to honoring the city’s pension commitments.

Enyia has been endorsed by celebrities such as Chance the Rapper and Kanye West, as well as former mayoral candidate Dorothy Brown. As of February 6th, Amara Enyia has raised $649,537, including a $400,000 donation from Chance.

-David Whyman

If Gery Chico won the election to become Mayor of Chicago, the position would be his first elected office. However, he has spent a great deal of time working in government, since his first internship during his undergraduate years. Chico got his start at the Department of Planning under Mayor Richard J. Daley, through a program at the University of Illinois, Chicago, that offered course credit for government service. He later went on to become the City Hall chief of staff to Richard M. Daley, the president of the Chicago Board of Education, the board president of the Chicago Park District, the board chairman of City Colleges of Chicago, and the chair of the Illinois State Board of Education. “How many times in your life have you said, I’m only going to do something for a short period of time,” Chico asked in a seminar through the Institute of Politics’ ChiElect. “I thought this was going to be one semester, and it turned out to be ten years.”

Chico has been endorsed by Reverend Herbert Martin, former Mayor Harold Washington’s pastor, and Rick Garcia, one of Illinois’ leading gay activists. He has also garnered the support of Alderman Ed Burke, who was arrested in the beginning of this year and was charged with corruption. Chico did not disavow his association with Burke, admitting that they were colleagues and that, were the recordings of Alderman Burke’s conversation ever made public, Chico may appear on them. However, he added that several other mayoral candidates, including Toni Preckwinkle, would likely be on the recordings as well. Top donors to Chico’s campaign include James Riley, a Cook County Circuit Court Judge, Nidia Puig, president of Puig Holding Co, and the local arm of the International Union of Operating Engineers.

In his ChiElect seminar, Chico said that his three top priorities as mayor are education, crime and policing, and reinvestment in communities. Chico worked with opponent Paul Vallas when the former was the president of the Chicago Board of Education and the latter was the CEO of Chicago Public Schools. Vallas has come under fire for not investigating sex abuse in the district during his time as CEO. With the prompting of moderator Laura Washington, Chico said he would repurpose the forty-nine schools that were shut down in 2013 into community centers and trade schools. “What’s happened since I left in 2001 is we have taken our foot off the gas pedal. And we have gotten a little bit soft. And most importantly, excellent educational opportunity is uneven across this city,” Chico said. Chico has also said he would fire Chicago Police Department superintendent Eddie Johnson and enforce the police department consent decree, with an emphasis on community policing. Chico supports a community benefits agreement with the Obama Presidential Center, but thinks it is unlikely to come about at this point in the development of the center.

-Kaeli Subberwal

As former Superintendent of the Chicago Police Department (CPD), Garry McCarthyhas had a long career in law enforcement. He worked his way through the ranks of the NYPD, playing a key role in coordinating the department’s response to the September 11 terrorist attacks. McCarthy later directed the Newark Police Department; shootings decreased by 46 percent across the Newark metropolitan area during his tenure. McCarthy was hired by a newly-elected Mayor Rahm Emanuel to lead the CPD in 2011. Though similar reductions in crime were reported, investigative reporting and an internal audit later suggested that some of the department’s progress was attributable to shifting categorization of murders. McCarthy was removed from office by Mayor Emanuel in the wake of the Laquan McDonald controversy.

McCarthy occupies a relatively complex position within the mayoral field as a candidate who appeals to conservatives — he described himself as a “conservative democrat” in an interview with the Chicago Tribune — despite holding some policy positions similar to those proposed by progressive community activists, such as reopening neighborhood schools closed during Rahm’s tenure and ending Mayor Emanuel’s cop academy project, which he considers a waste of city funds. McCarthy has slowly shifted his position from the only alternative to Rahm into a crime-focused candidate appealing to dissatisfied white Democratic voters and the city’s few conservatives. Despite this appeal, he has been endorsed by prominent progressive Chicago community activist Andrew Holmes, who cited McCarthy’s ability to listen to City residents as the reason for his endorsement. Donations to his campaign have come from various businesses and private individuals, without a clear ideological trend, resulting in over one million to date.

McCarthy focuses his campaign on three core policy areas: education, taxes and the economy, and crime. He aims to avoid the “bullying politics” he feels characterized the Emanuel administration and seeks to increase public access to the mayor. In order to establish an “Open and Honest Government,” McCarthy has issued twelve proposals aimed at reducing corruption and increasing accountability. These include monthly mayoral town hall meetings to be held in neighborhoods across the city McCarthy is also focused on reinvestment in neighborhood schools using proceeds from schools sold under Mayor Emanuel’s tenure. He plans to initiate a partially-elected school board and will seek to expand services for special needs students, women and children. In regards to crime, McCarthy has another twelve point plan which includes a review of the CPD’s disciplinary system, a data-driven approach to reducing crime rates, and improving existing training and community relations programs. McCarthy considers crime a socioeconomic issue with roots in divestment from low-income and African American communities, and aims to combine education and improved police-community relations to address the root causes of criminal activity. Finally, McCarthy’s financial program seeks to reduce wasted funds through performance-based assessment of city departments. He aims for fiscal discipline, with adherence to budgets and minimized borrowings, as well refilling of pension coffers and preventing politically-motivated lowering of property tax assessments. Regarding the Obama Presidential Center, McCarthy stated at a debate in December, “I do agree with the community benefits agreement… but I do think that there needs to be a stimulus package attached . . . this should be stimulating economy and jobs in the neighborhood.”

Primary criticism of McCarthy includes his handling of the Laquan McDonald shooting, in which a 17-year old African American teen was shot by CPD officer Jason van Dyke, who was later charged with second-degree murder and 16 counts of aggravated battery. Despite seeing video of the incident in the days after it occurred, under McCarthy’s leadership the CPD failed to release the video for nearly 400 days, until court intervention. A U.S. Department of Justice investigation into the CPD later found some its members engaged in “racist and abusive behaviors” due to “systemic and cultural failings.” Activist calls for reform were answered by Mayor Emanuel’s decision to terminate McCarthy’s leadership of the CPD shortly after the video of the shooting was released. McCarthy blamed the situation on the Chicago Police Board, which he claims did not allow the removal of officers he identified as problematic.

-Alex Shura

Lori Lightfoot, the first openly lesbian mayoral candidate in Chicago’s history, has never held elected office, but she has a long history of public service for the city. Outgoing Mayor Rahm Emanuel selected Lightfoot to lead President of the Chicago Police Board (CPB), a civilian-led organization that investigates and disciplines police officers for alleged misconducts and abuses, as well as to build and chair the Police Accountability Task Force (PATF). Lightfoot left her position on the CPB in May of last year before Emanual’s announcement that he would not be running for Mayor in the upcoming election; she has criticized her opponents who entered race later in the game for lacking the strength to run “before Goliath was slayed.” Lightfoot attended the University of Chicago Law School on a full scholarship and graduated in ’89.

Lightfoot has been endorsed by the Chicago Sun-times Editorial Board, who commended her storied record of public service, including convicting a Chicago Alderman for bribery, transforming the CPB from a fairly toothless bystander of police abuses into an organization that fired 72 percent of officers in the cases it examined, and particularly, publishing a damning PATF report on the Chicago Police Department’s (CPD) worst practices following the shooting of Laquan McDonald. (The report spurred the writing and eventual passage of the Chicago Police Department’s (CPD) Consent Decree, which establishes court-ordered mandatory reform measures for the CPD). She has also received endorsements from the Victory Fund, a national organization dedicated to electing openly LGBTQ+ candidates, as well as Illinois Educational Association Region 67, which is made up of higher education employees in the city. In terms of fundraising, Lightfoot’s funds are smack in the middle of the mayoral candidate’s respective coffers. She’s raised about $1.5 million to date; her largest donor is herself.

Drawing from her time in the police reform world, as well as her former role as a federal prosecutor, Lightfoot has championed herself as an experienced police reform advocate and anti-corruption candidate. She drafted a list of ethics reforms entitled the People First Pledge, which commits signatories to running for only one position at a time and imposes two-term limit for both mayoral and aldermanic chairman City Council positions; the pledge was signed by 15 aldermanic challengers. Her plan to clean up city government centralizes and strengthens the Office of the Inspector General and brings transparency to Tax-Increment Funding (TIF), a controversial public-financing method that re-allocates property taxes to a fund that encourages development in blighted areas of the city. Lightfoot has also emphasized investing in local schools & neighborhoods, protecting LGBTQ+ and immigrant rights, expanding affordable housing options, as well as funding and making accessible art and culture.

Criticism of Lightfoot includes two lawsuits she worked on during her time at law firm Mayer Brown; both suits were introduced by Republicans challenging the redrawing of Congressional districts. Had the suits been successful, several current elected representative of the Democratic party, including the popular Tammy Duckworth (D-8th), could not have won their elections.. Lightfoot stands by her work, arguing she was fighting the hyper-powerful Democratic power structures that often inhibit the prospects of minority candidates — she claims the map, which ultimately passed, “screwed Latinos, plain and simple.”

-Alia Shahzad

Willie Wilson is a Chicago businessman who founded and owns Omar Medical Supplies, produces the gospel music entertainment show Singsation, and has owned and managed a variety of other businesses in the past, including multiple McDonald’s franchises. Active in the black church community, Wilson also founded and serves as chairman of the trustee board of Chicago Baptist Institute International. Though he has not held any political office positions, he ran for Mayor of Chicago in 2015 and garnered 11 percent of the vote. He also ran for President of the United States in 2016. Wilson grew up in Gilbert, Louisiana and moved to Chicago in 1965. he has a Doctor of Divinity Degree from Mt. Carmel Theological Seminary.

Wilson’s economic platform includes a property tax freeze, legalizing and taxing marijuana, legalizing and taxing citizen-owned casinos, as well as setting aside funds to create community-based grants to help small businesses. In addition, Wilson has pledged to end police brutality and cover-ups, end political corruption via a politically progressive city council, create an elected school board, as well as support retention of Chicago’s sanctuary city status. He is in favor of setting two-term limits for Chicago mayor. He has also committed to make the CTA free for seniors.

Wilson has provided the vast majority of the funding for his campaign, putting in most of the $1.5 million raised during his campaign’s course . He has received the endorsements of the Cook County Republican Party Chairman Sean Morrison and Chicago Young Republicans. Wilson touts these endorsements as a sign that he can unite voters across the political spectrum.

Wilson has been criticized by many for his past support of Bruce Rauner and Donald Trump, although Wilson has stated that he regrets those decisions. He was accused of “vote-buying” after giving out $500 checks to help people pay their taxes through his charitable foundation. Wilson has also been criticized for his lack of political experience.

-Gianluca Yong

Neal Sáles-Griffin is a businessman, college professor, and CEO of the non-profit organization CodeNow, which promotes free workshops across the country to teach children how to code. Sáles-Griffin grew up on the south side of Chicago, in the South Shore and Hyde Park neighborhoods. On the campaign trails, he talks about how these experiences shaped him-- in one anecdote, he recalls seeing someone shot when he was only eight; in another, he recalls being physically harassed by police when he was a fifteen year old. A graduate of Northwestern University, Sáles-Griffin would go on to found several business ventures and work in venture capital. At 23, he quit his job to start up a non-profit to run coding workshops for children, which evolved into CodeNow.

Politically, Sáles-Griffin is a complete outsider. His fundraising comes mostly from his own pocket, as well as his friends. His friend Jason Fried, CEO of local tech firm Basecamp, is his largest donor, and Basecamp’s west loop office serves as Sáles-Griffin’s campaign headquarters. Sáles-Griffin’s biggest donations have come through Unite Chicago PAC, which is chaired by Cards Against Humanity co-creator Max Tempkin, and has received donations mainly from Fried and Gregg Latterman, a record company CEO and angel investor. In interviews, Sáles-Griffin has called out the high cost of running for public office as a problematic barrier that keeps public service “inaccessible” for many people.

Sáles-Griffin struggled early in the campaign, “bombing,” in his own words, his announcement speech. Since then, he’s talked about how his unique life experience and deep links to the city makes him a good fit for the role. His background in tech comes through in some of his interviews, and his suggestions to do a sweeping audit of the city’s public services, and to radically increase transparency, sound like he’s trying to bring the spirit of a tech startup to how he would lead the city.

Sáles-Griffin’s political platform mixes several themes. He wants to expand government services that help the poor and help children: an expansion in pre-K programs, an increase in affordable housing, a new office to oversee vocational training programs in the city. He wants to approve government accountability, endorsing an elected school board instead of an appointed one and calling on limits on campaign donations from special interests. Other policies seem to be informed by Sáles-Griffin’s background. As the son of a cop and a victim of police harassment, he’s called for using a data-driven approach to identify and eliminate racial disparities in policing, and for more police officers to be recruited from the neighborhoods that they patrol. As a teacher, he’s calling for the creation of a Youth Council to include the voices of young people in government. As a long-time Chicago business person, he emphasizes the importance of investing in Chicago’s small business, but condemns past deals the city has made with big businesses, as these businesses usually get tax breaks without being required to invest in the city.

-Sam Owens

Born in St. Louis Missouri, Kevin Bailey has spent much of his life around the ward he is now vying to represent. He grew up on Chicago’s south side, attended and graduated from the University of Illinois Urbana Champaign with a degree in Civil Engineering, and then worked as a civil engineer for former President Barack Obama’s high speed rail initiative. He was the first black engineer on that project. He then returned to the city, challenged outgoing alderman Willie Cochran for his seat in 2015, and after finishing a close second became the 20th ward Democratic committeeman. In that role, he’s opened a community service center; he’s also a member of the Washington Park Resident Advisory Council (WPRAC) and the Residents Association of Greater Englewood (RAGE), among other community organizations.

Bailey has been active in Chicago Democratic politics for years. He’s organized and volunteered for the campaigns of former Cook County Clerk Dorothy Brown, Congressman Danny Davis, and Aldermen David Moore and Chris Taliaferro, among others, according to his campaign website. Both Moore and Taliaferro are members of the City Council’s Progressive Reform Caucus. His fundraising committee, “Citizens to Elect Kevin Bailey”, has around $20,000 in funding as of December 31st 2018 (their last report date). Their top donors are Bailey himself ($13,000) and “JB For Governor” ($5,000).

On the issues, Bailey has mostly held the party line. In an interview with the Chicago Maroon, he named gun violence as his campaign’s priority, and advocated for better mental health resources for citizens and police, as well as reintegration programs for the formerly incarcerated. He also voiced support for a Community Benefits Agreement (CBA) ordinance regarding the Obama Presidential Center.

Bailey has, however, been sharply criticized by opponents for what they claim is corrupt Chicago politics. He challenged the signatures all his opponents but one; city council candidates are required to get a few hundred signatures from ward residents to appear on the ballot. Though many of his objections have been thrown out, they have cost his opponents weeks of work and thousands of dollars.

Moreover, Kevin Bailey’s mother, Maria Bailey, is a Republican Committeeperson, despite working as the notary and petition circulator of his campaign. A Chicago Reader investigation found that 65 percent of the ward’s 150 election judges were appointed by one of the Baileys. These judges are supposed to be nonpartisan, but since the Baileys took control of both sides of the 20th Ward committee, accusations of impropriety have arisen. The Reader documents six such cases.

-Jake Gosselin

Maya Hodari is currently the director of development for the Chicago Housing Authority. She has a background in community organizing in Woodlawn: she developed the Woodlawn Community Association in 2008, co-organized the first Woodlawn Community Summit, and has been a member of the Chicago Mid-South Anti-violence Collaborative, the South East Chicago Commission, and the Woodlawn Public Safety Alliance. Hodari is in favor of a Chicago casino and greater transparency in tax increment financing (TIF) funding. She is in favor of an elected school board (currently the school board is appointed by the mayor). She is also a strong supporter of the Obama Presidential Center, which will be built in Jackson Park. She has not said whether she would support a community benefits agreement to protect local interests surrounding the project.

-Kaeli Subberwal

A community organizer and activist, Jeanette Taylor has been involved on several high-profile campaigns affecting the 20th Ward and the larger South Side. Long involved in issues surrounding Chicago Public Schools, Taylor sat on her Local School Council for 21 years after graduating from CPS and led the hunger strike for the re-opening of Dyett High School. Taylor has also been a vocal critic of the Obama Foundation’s decision to not sign a Community Benefits Agreement for the Obama Presidential Center and has helped in the efforts for the University of Chicago Hospital to open an adult trauma center. In the past, Taylor has worked as a community organizer for the Kenwood Oakland Community Organization. Based upon her organizing experience, Jeanette Taylor is running on being “the only candidate with a track record of taking on Rahm Emanuel and winning.”

Taylor’s campaign for alderman of the 20th ward is endorsed by a number of grassroots organizations and unions. Among these are the Chicago Teachers Union, the People’s Lobby, United Working Families, Chicago Federation of Labor, Teamsters 700, Chicago Democratic Socialists of America, and State Representative Delia Ramirez. She currently has over $81,000 in campaign funds as of February 17th, with substantial donations from aforementioned endorsing organizations.

Jeanette Taylor’s top three priorities are housing, education, and economic justice. She is focused on stopping the displacement of low-income residents and people of color by ensuring affordable housing and rent control, creating fully-funded schools that are hubs of community programming, having an elected school board, ensuring a living wage and right to organize with the new developments in the ward, and creating a business corridor along 63rd street. Other parts of her platform include community safety, empowering youth and elders, immigration justice, and environmental leadership. Taylor is particularly critical of aldermanic prerogative and practices that exclude residents from the decision-making process. She is in support of decisions being decided centrally under an equitable development plan and for an inspector general to audit Chicago City Council, especially with respect to zoning.

-Claire Cappaert

Andre Smith was born and bred in the South Side of Chicago. An activist preacher, he graduated from East West University in 1990 and the Moody Bible Institute in 1998.

Smith has run twice before for this seat on the City Council: once in 2010, and then again in 2014. Most recently he finished third, behind Kevin Bailey (who’s running against him once again) and outgoing alderman Willie Cochran. His background is in activism; Smith has protested against school closings, worked with Southside Together Organizing for Power (STOP) to fight evictions, and was part of the movement that got the University of Chicago to open an adult trauma center on the South Side.

Smith’s platform includes a commitment to an elected school board, funding for mental health facilities on the South Side, and an increased affordable housing for low income Chicagoans. According to the Chicago Maroon, he’s also committed to a community benefits agreement regarding the Obama Library.

Smith’s campaign committee, “Friends of Andre Smith”, had $6,638.90 as of December 31st, 2018. Its top donor was Rollin Warden.

-Jake Gosselin

Quandra Speights grew up on the South Side of Chicago, graduating from Fenger High School in Roseland. She has a bachelor’s degree from Clark Atlanta University, and a law degree from Valparaiso University. She currently works as an estate planning attorney.

Speights, in her interview with the Chicago Sun Times, cited her background in campaign advocacy and lobbying as experience she would bring to the city council. She has worked on the board of SheVotes, a political action committee that aims to “highlight the importance of women’s voices in elections, government, and policymaking.” She’s also worked on the board of No Shots Fired, an organization dedicated to ending neighborhood violence. Her political action committee, “Citizens to Elect Quandra Speights”, had $56 on hand as of December 31st, 2018.

On the issues, Speights has cited economic development, crime reduction, and government transparency as her top three priorities. She has advocated for strengthening the Cottage Grove, 63rd Street, and 51st Street corridors by working with the Department of Planning and “stakeholders” in the community. She has also voiced support for a CBA ordinance for the Obama Presidential Center.

-Jake Gosselin

An an Englewood native, first-time candidate Nicole Johnson has a history of community engagement that she’s seeking to expand to the rest of the ward. Johnson holds three degrees, including a B.A. in Political Science from the University of Michigan, an M.A. in Teaching from National Louis University and an M.S. in Education Policy at the University of Pennsylvania Graduate School of Education. As an employee of Chicago Public Schools, Chicago Votes, a young voters’ engagement non-profit organization, and Teamwork Englewood, a community organizing non-profit. She has experience in education, communications, and public policy through her roles at Chicago Public Schools, Teamwork Englewood, and Chicago Votes. During her time at Teamwork Englewood, Johnson developed a review process facilitating communication between the alderman and community about ward projects such as zoning changes. and plans on expanding this system to the entire 20th ward. During her time at Chicago Votes, she also worked with Chance the Rapper’s Parade to the Polls as an outreach manager.

Despite Johnson’s lack of experience in public office, she has raised double the funds as the next most-funded candidate, Kevin Bailey. So far she has secured endorsements from the Resurgent Left, Brand New Council, Independent Voters of Illinois, Run for Something, and Chance the Rapper. Her donors also come from varied political backgrounds: Peter Kadens, former CEO of Green Thumb Industries (a cannabis provider), is her top donor and consistently donates to Democratic candidates. Two other top donors have donated to the Republican party: Timothy Schwertfeger donated to former Illinois Governor and Republican Bruce Rauner while Ashley Joyce donated to the Chicago Republican Party and heads the Duchossois Family Foundation, which gifted UChicago $100 million in 2017.

Johnson leans strongly blue, and focuses on similar areas of interest as her co-candidates. Her top three issues are safer communities, economic empowerment and building exceptional schools. Key policy proposals include creating an independent community board to oversee CPD, creating a community land trust directed towards increasing affordable housing and local business, and bringing cross-institutional partnerships and wraparound services, such as extended hours and workforce development programs, to local schools. Johnson acknowledges the diversity of resident responses to police: some feel fearful whereas others feel safer, even with increased police presence stemming from CPD and UCPD overlap. To mediate these views, she has focused on improving community-police relations and supports the consent decree as well as a community oversight ordinance. Like most of the 20th ward’s candidates, Johnson supports a Community Benefits Agreement for the OPC and is also a Peer Advisor to the Obama Foundation. She has also signed Common Cause Illinois’s pledge supporting voluntary publicly-funded elections.

The Chicago Reader noted that Johnson was one of two 20th ward candidates to challenge other candidates’ eligibility for the ballot. She challenged 2,727 signatures (candidates need 12,500 to officially enter the race), all from other female candidates, including Maya Hodari and Jennifer Maddox. Maddox suggested Johnson’s challenges indicated a deterrence tactic rather than a substantive challenge on policy-based grounds. When asked why she had not challenged Bailey despite challenging other candidates, Johnson responded that Bailey would likely have made the ballot even despite being challenged.

-Miranda Zhang

Leslie Hairston is the incumbent 5th Ward Alderman in the race. A native to the Hyde Park and South Shore communities, an alumnus of the University of Chicago Lab School, and graduate of Loyola University Law School, Hairston worked as a private attorney before entering government work as an Assistant Attorney General. Hairston is a member of multiple community advisory councils, and works on six committees on the Chicago City Council: finance; health and environmental protection; cultural affairs and recreation; special events, budget and governmental operations; and committees, rules and ethics. Hairston also currently holds the position of vice chair for economic, capital, and technology among several joint committees on the Council.

Hairston supports and has introduced legislation in the City Council to reform how Tax Increment Financing funds are allotted, and to allow for more transparent development projects to occur in blighted communities. Hairston does not support a Community Benefits Agreement for the Obama Presidential Center, and tends to vote in favor of Chicago Mayor Rahm Emanuel’s proposals over 75% of the time. She has strongly touted her record of development in her ward, with stores, hotels, and community centers often constructed by minority owned firms. Since 2014, her office has provided open forums for local residents to determine how $1.4 million dollars in discretionary “menu” spending is spent within the 5th ward.

-Richard Omoniyi-Shoyoola

Gabriel Piemonte is a former editor of the Hyde Park Herald and works with a variety of community organizations. He is the founder of Woodlawn Voices and Visions, a Summer videography program for CPS students, and South Side Community Federal Credit Union, a credit union that provides low-interest loans and banking services to members of the community. He has a B.A. in communication and journalism from Suffolk University. This is his first time running for a political office.

Piemonte is a Democrat, but tends to take a more progressive stance on most issues. He has frequently criticized other politicians for failing to involve the community in decision-making. Piemonte has received endorsements from the South Side chapter of Democracy for America, the editorial board of the Chicago Sun-Times, the editorial board of the Chicago Tribune, the editorial board of the Hyde Park Herald, and the editorial board of the Chicago Maroon. He has raised $20,000 in campaign donations.

His platform is centered around encouraging civic engagement, bolstering the local economy, and allowing community input in local preservation projects. He supports a community benefits agreement for the Obama Presidential Center and has also called for the building site to be renegotiated. He would seek to improve the relationship between law enforcement and the community by forming a Civilian Police Accountability Council to oversee the police. He also supports the creation of local development councils to check aldermanic privilege and oversee development projects. He is in favor of having elected school boards and placing a moratorium on charter school development. He wants to expand public housing opportunities and social services. He also wants to make the relationship between the University of Chicago and the surrounding community more equitable and supports Graduate Students United.

-Gianluca Yong

A well-known activist and organizer, William Calloway is most notable for his work with journalist Brandon Smith to bring about the release of the Laquan McDonald shooting video. The video provoked outrage, prompted the conviction of the officer involved, and contributed to the termination of former CPD Superintendent Garry McCarthy and electoral defeat of State’s Attorney Anita Alvarez. Last spring, Calloway ran for a seat in the Illinois House of Representatives. He was defeated in the Democratic primary by Curtis Tarver II. Calloway has not earned a post-secondary degree, though he has completed some college coursework.

William Calloway has run as a Democrat in past elections and supports members of that party. However, he has criticized many Democratically-affiliated Chicago politicians over the past several years for their perceived failure to take action to help all members of the communities they serve. Calloway is therefore best seen as a sort of independent-Democrat hybrid, focused on reform and public service over partisan considerations. He has been endorsed by the editorial board of the Chicago Tribune and has raised $5,500 to date from small donor contributions.

Calloway has several main priorities for the development of the 5th Ward. He aims to improve community-law enforcement relations to promote a feeling of safety, bring grocery stores to the area to decrease the number of food deserts, and help the CPS schools in the ward perform at a consistently high level. Calloway would like an all-elected school board and a moratorium on new charter schools. Generally opposed to increased municipal taxes, Calloway would sanction a tax on legalized marijuana, especially if some of the revenue from the tax could be set aside for marijuana-related conviction rehabilitation. He also wants a 10 percent pay cut for alderman and a 3-10 percent salary decrease for various departmental leadership positions across the city.

Calloway has been widely praised for his role in exposing the Laquan McDonald shooting tape. Criticism of him is generally limited to his policy positions and lack of governmental experience.

-Alex Shura