How the Chicago City Council election is shaping up: Who’s facing steep competition, and who’s getting a free pass

As Chicago gears up for next year’s citywide election, it’s already apparent that the future makeup of City Council could seismically shift this February.

Though less high profile than the mayor’s race, the aldermen who represent Chicago’s 50 wards wield their own powers in shaping the city, from voting on hallmark legislation to making sure broken streetlights get fixed. And with 15 aldermen this year having announced impending retirements, opted to run for other offices, or already left — in one case forced by a criminal conviction — City Council could look a lot different come the next term that starts in May.

This election — which takes place Feb. 28, with an April 4 runoff if needed — will also be the first using a newly redrawn ward map, a process that happens just once a decade.

With the nominating petitions filing period now over, the contests for the next council are taking shape. There’s still room for signature challenges to knock off contenders, but as of now, here are the highlights to watch out for in Chicago’s aldermanic races.

Incumbents, contested and uncontested

A handful of City Council members are guaranteed another term, as no one has filed to challenge them. Downtown Ald. Brian Hopkins, 2nd, is running unopposed for reelection after he mulled, but decided against, a run for mayor. Ald. David Moore, 17th, will have no challengers either.

In the 27th Ward, Ald. Walter Burnett, who is close with Mayor Lori Lightfoot, is unopposed in his bid for reelection. So is Finance Chair Scott Waguespack, a longtime leader in the council’s Progressive Caucus and an ally to the mayor, in the 32nd Ward. Ald. Matt Martin, who has often aligned himself with leftist members of the City Council, is similarly assured a second term representing the 47th Ward.

That said, most sitting aldermen who seek another term will have to campaign for that victory. In the 1st Ward, for example, freshman Ald. Daniel La Spata is facing a challenge from the man he beat in 2019: Proco “Joe” Moreno, a controversial figure who has been embroiled in legal scrapes. Also running are Sam Royko, the son of famous columnist Mike Royko, as well as Stephen “Andy” Schneider.

Ald. Brendan Reilly, often the council’s most cash-flush member, could face his first opponent since defeating incumbent Ald. Burt Natarus in 2007. Chris Cleary, a former vice president at BMO Harris Bank, according to his campaign website, has filed to represent the 42nd Ward, which includes much of the Loop and River North.

Ald. Gilbert Villegas, 36th, who led a failed bid to boost majority-Latino wards during the remap, is running for reelection in a vastly different 8-mile-long ward that stretches through multiple neighborhoods from West Town to the Far Northwest Side. Villegas faces three challengers: Leonor “Lori” Torres Whitt, David Herrera and Jacqueline “Jackie” Baez.

Open seats

There are slated to be 11 open seats in the 2023 aldermanic races: the 4th, 5th, 6th, 10th, 14th, 21st, 30th, 34th, 44th, 46th and 48th wards. Most are attributed to sitting City Council members announcing their retirements at the end of this term in May, though two are forgoing reelection bids in order to seek the mayor’s office: Sophia King, 4th, and Roderick Sawyer, 6th.

In the 12th Ward, George Cardenas also retired this month after winning his general election campaign for the Cook County Board of Review, but Lightfoot is expected to appoint his replacement ahead of the 2023 election, giving that pick an incumbency advantage if they choose to seek a full term. Those who submitted their names for Lightfoot’s consideration include Anabel Abarca, Cardenas’ former chief of staff who is also running for the seat in February. Other contenders in the 12th’s election race are Julia Ramirez and Joseph Mercado.

Two retiring aldermen chose to vacate their seats early this year — the 43rd Ward’s Michele Smith and the 24th’s Michael Scott — while a third, Patrick Daley Thompson of the 11th Ward, was forced out after being convicted of felony tax fraud. Lightfoot has already seated replacements for those three — Nicole Lee in the 11th; Timmy Knudsen in the 43rd; and Scott’s sister, Monique Scott, in the 24th — and each is running to keep their seats this February.

In the 4th Ward, seven candidates are throwing their hat in the ring to replace King in representing swathes of downtown, the South Loop and Bronzeville. They are state Rep. Lamont Robinson, Matthew “Khari” Humphries, Tracey Bey, Helen West, Ebony Lucas, King’s chief of staff Prentice Butler and Paul Pearson.

Ald. Leslie Hairston has an even longer list of hopefuls for her 5th Ward seat when she retires. They are: Marlene Fisher, Renita Ward, Adrienne Irmer, Joshua Gray, Robert Palmer, Wallace Goode, Lightfoot’s former chief engagement officer Martina “Tina” Hone, Jocelyn Hare, Desmon Yancy, Gabriel Piemonte, Dialika “Dee” Perkins and Kris Levy.

Sawyer’s 6th Ward generated similar interest, with Richard Wooten, Kirby Birgans, Barbara Ann Bunville, Sylvester Baker Jr., O. Patrick Brutus, William Hall, Steven Dejoie, Curtiss S. Llong Bey, Sawyer’s ward assistant Paul Bryson Sr., Sharon Pincham, Tavares Briggs, Aja Kearney and Kimberly “Kim” Egonmwan submitting their names for the ballot.

For the 10th Ward seat, from which Ald. Susan Sadlowski Garza is retiring, five candidates are vying to succeed her: Ana Guajardo, Jessica Venegas, Peter Chico, Yessenia Carreón and Oscar Sanchez. Guajardo is a former organizer with Service Employees International Union Local 1, while Sanchez is a community activist who went on a hunger strike last year to protest General Iron’s bid for a city permit.

The 14th Ward, home to Ald. Edward Burke, has just two contenders to replace the City Council giant who opted not to run for reelection after more than a record 50 years as he faces a trial for wide-ranging corruption. The filed candidates are Jeylu Gutierrez, a staffer of Cook County Commissioner Alma Anaya, and Raul Reyes, a Burke lieutenant.

Another long list of contenders is running for the 21st Ward seat that Ald. Howard Brookins Jr. will vacate at the end of this term: Patricia Tillman, Cornell Dantzler, Tawana “T.J.” Robinson, Justin Sawyer, Larry Lloyd, Preston Brown Jr., Lawaco Toe, Ronnie Mosley, Daliah Goree, Nekoiya Washington, Bernard “BK” Kelly, U.S. Rep. Bobby Rush’s aide Ayana Clark, Aziza Butler and Kweli Kwaza.

Six candidates have filed to run in the open race to succeed retiring Ald. Ariel Reboyras in the 30th Ward. Jessica Gutierrez, the daughter of former Congressman Luis Gutierrez, is trying for a second time to win the seat after forcing Reboyras into a runoff in 2019 and losing by 302 votes. Also running: CTA Director of Diversity Programs Juanpablo Prieto, Warren Williams, Ruth Cruz, Andrew Cleaver and former general counsel for Chicago’s Office of Inspector General Rory McHale.

There are two candidates in the open 34th Ward race to replace Carrie Austin, who will exit the council in March amid a federal criminal indictment. The oddly shaped ward, redrawn during redistricting, now includes parts of the Loop, Greektown and the campus of the University of Illinois Chicago.

Bill Conway — a former assistant Cook County state’s attorney and son of the billionaire co-founder of the private equity firm The Carlyle Group — filed first. Backed by his father’s fortune, Conway ran for Cook County state’s attorney in 2020 but was defeated in the Democratic primary by incumbent Kim Foxx. Ascot Realty CEO James Ascot, the past president of the Chicago Association of REALTORS, has also filed to run.

North Side lakefront wards stretching from Lincoln Park to Edgewater are also in flux. For example, in the 46th Ward, six candidates have filed for the open seat to replace retiring Ald. James Cappleman, who has represented the Uptown ward since 2011. The ward is among the targets of the progressive group United Working Families, who have endorsed Angela Clay. Others who have filed to run for the 46th seat are Kim Walz, Patrick Nagle, Roushaunda Williams and Marianne Lalonde, who came in second to Cappleman in 2019.

Just north, the 48th Ward race to succeed retiring Ald. Harry Osterman is even more crowded, with 10 candidates who have filed to run. Joe Dunne, Isaac Freilich Jones, Andre Peloquin, Leni Manaa-Hoppenworth, Brian Haag, Nick Ward, Larry Svabek, Nassir Faulkner, Roxanne Volkmann and Andy Peters all submitted petitions.

Donors

Key to this year’s races will also be donors. While unions have been heavily involved in campaign spending for decades, in recent years, charter school associations, real estate agents and allies of Mayor Rahm Emanuel formed independent expenditure political action committees to support their preferred candidates or bash their rivals.

A new committee is emerging in this campaign cycle to sway aldermanic races. The yet-unnamed PAC is starting up to focus on electing pragmatic, pro-business candidates who will focus on addressing crime and creating a thriving business environment for the Loop and other retail corridors, according to the group’s chair, former Emanuel staffer Mike Ruemmler.

“We’re looking for workhorses, not show horses,” Ruemmler told the Tribune, describing the group’s target candidate as “Obama Democrats” who have the best interests of the city at heart, not their own ambitions. Ruemmler says the PAC has no plans to get involved in the mayoral race.

Already lined up to contribute, Ruemmler says, is Michael Sacks, a longtime Emanuel supporter and CEO of asset management firm GCM Grosvenor. Ruemmler says he hopes to attract a diverse set of donors from both the business and labor community.

Sacks and his wife, Cari, are prolific political givers, and Emanuel was among their top beneficiaries. The Sackses have also donated to Lightfoot and the PAC supporting her, but to a far lesser extent than Emanuel.

Michael Sacks has also recently given to Conway for his 34th Ward aldermanic bid and to 50th Ward Ald. Debra Silverstein, who faces CTU-backed challenger Mueze Bawany.

An independent expenditure committee newly set up by Lightfoot backers, the 77 Committee, could also potentially benefit her allies on the council.