One of these fourteen people will be Chicago's next mayor.
Voters in Chicago have been going to the polls for weeks now, and on Tuesday they will have one last chance to vote on the future of the city. The mayoral race is wide open with the retirement of Rahm Emanuel, but there is plenty of excitement up and down the ballot, with two other citywide positions and fifty (yes, fifty) aldermanic seats also up for election. In this diary I’ll take you through all the races, starting with the mayoral contest. (Note that in Chicago, municipal elections have been nonpartisan since 1999, after the Republican candidate for Mayor only received 4% of the vote in 1995. If no candidate in a race receives more than 50% of the vote on Tuesday, they will advance to a runoff on April 2. However, most of the candidates running identify as Democrats, with a few exceptions.)
Fourteen candidates made the final ballot for mayor: attorney Jerry Joyce, former Chicago Public Schools CEO Paul Vallas, businessman and 2015 mayoral candidate (and 2016 presidential candidate) Willie Wilson, Cook County Board President Toni Preckwinkle, former Obama CoS William Daley (who also served as Commerce Secretary under Bill Clinton and is a member of the famous/infamous Daley clan), former Chicago Police Chief Garry McCarthy, long-serving public servant Gery Chico (who ran for mayor in 2011 and for U.S. Senate in 2004), State Comptroller Susana Mendoza, public policy advocate Amara Enyia, State Representative La Shawn Ford, entrepreneur Neal Sales-Griffin, former chair of the Chicago Police Accountability Task Force Lori Lightfoot, former Alderman and 2015 mayoral candidate Bob Fioretti (who challenged Preckwinkle for Cook County Board President in 2018), and attorney John Kozlar (who ran for 11th Ward Alderman in 2015).
Regardless of fundraising, there will be a runoff here, as no candidate is guaranteed to get over 50% of the vote in February. My guess is that Toni Preckwinkle and Bill Daley advance to the April runoff. While Preckwinkle’s campaign has had plenty of turmoil, she still has the endorsement of the Chicago Teachers Union (CTU), which will provide much-needed ground support for her candidacy. Lori Lightfoot has stolen some support from her, but I don’t think it will be enough to deny her a place in the runoff. As for Daley, the city’s conservatives seem to have consolidated around him instead of McCarthy or Wilson, believing that putting a Daley back in charge will “make Chicago great again”. However, I wouldn’t count out anybody’s chances of advancing to the runoff, with the exceptions of Joyce, Ford, Sales-Griffin, Fioretti, and Kozlar.
As for the other citywide races, appointed City Clerk Anna Valencia will get a full term of her own as she was the only candidate to qualify for the ballot. She replaced Mendoza after Mendoza became Comptroller in 2017. Meanwhile, three candidates are running to succeed City Treasurer Kurt Summers, who is retiring. They are State Representative Melissa Conyears-Ervin, 47th Ward Alderman Ameya Pawar (who briefly ran for Governor last cycle), and CPA Peter Gariepy, who ran unsuccessfully for Cook County Treasurer last cycle. Compared to his opponents Gariepy hasn’t really raised anything, so this is really a two-person race that could go to a runoff. Not sure who I would pick to win between the two, but I am rooting for the more progressive Pawar.
Now to the aldermanic races! Five aldermen are running for reelection unopposed: Brian Hopkins (2nd Ward, Near North Side), Scott Waguespack (32nd Ward, Wicker Park/Bucktown/Logan Square), Gilbert Villegas (36th Ward, NW Side), Nicholas Sposato (38th Ward, Old Irving Park), and Brendan Reilly (42nd Ward, Downtown). Hopkins, Villegas, and Reilly are Emanuel allies, Waguespack is a progressive, and Sposato was part of the progressive caucus until he left over issues such as immigration.
Sixteen aldermen are running for re-election with one challenger, which means that their races will be decided on Tuesday. They are:
- Proco Joe Moreno (1st Ward; Logan Square, West Town, and Wicker Park). Moreno briefly ran for IL-04 last cycle. Although he positions himself as a progressive, his ties to real estate developers (and therefore gentrification) has made him a top target for Chicago progressives, especially since he barely avoided a runoff in 2015. Community organizer Daniel LaSpata is challenging him; however, he lags Moreno in fundraising. The headlines in this race have been wild: Moreno has been accused of filing a false police report and of sexual harassment, while LaSpata was caught in an insensitive photo from his bachelor party several years ago. It’s hard to say who will win, but if I had to guess I’d say Moreno gets a narrow victory on Tuesday.
- Pat Dowell (3rd Ward; Bronzeville). Dowell is pretty good on most issues. She faces a challenge from healthcare analyst Alexandria Willis, who has raised comparatively little (less than $5K) compared to Dowell’s $180K. Dowell should win re-election handily.
- Sophia King (4th Ward; Bronzeville, Kenwood, and Hyde Park). This is President Obama’s ward, as well as Toni Preckwinkle’s old ward. King was appointed in 2016 after Preckwinkle’s successor, Will Burns, resigned to become a lobbyist for AirBnB. A member of the Progressive Caucus, she won a 2017 special election and now is running for her first full term. Attorney Ebony Lucas is challenging her; although she had a decent fundraising quarter ($26K) she only has about $8K on hand vs. King’s $65K. King should get her full term without much trouble.
- Susan Sadlowski-Garza (10th Ward; Hegewisch; East Side; South Deering). A CPS counselor and daughter of the late labor organizer Ed Sadlowski, Sadlowski-Garza unseated establishment Alderman John Pope in 2015. She’s being challenged from the right by attorney Bobby Loncar. Loncar has about $15K on-hand versus Sadlowski-Garza’s $74K. Loncar should be competitive but he’ll likely fall short of unseating the progressive Sadlowski-Garza.
- Patrick Daley Thompson (11th Ward; Bridgeport). The nephew of the Daleys won election to this open seat in 2015 by a surprisingly close margin. Labor activist David Mihalyfy is his sole challenger for re-election. Mihalyfy also has not raised any money, so Daley Thompson should be a lock for a second term.
- Marty Quinn (13th Ward; West Lawn, Clearing). This race has been one of the most bizarre this cycle. Quinn (no relation to former Governor Pat Quinn) is literally a pawn of Mike Madigan; just look at his website URL. He ran unopposed in 2011 and 2015 but has seen a barrage of bad headlines over the past year, starting with allegations of sexual harassment against his brother Kevin, an employee in the Madigan Organization. More recently, his campaign took aggressive measures to keep challenger David Krupa, a DePaul University student who helps run a chapter of far-right Turning Point USA on the campus, from reaching the ballot, although his campaign was forced to drop those challenges thanks to public pressure. Conservatives such as former state representative Jeannie Ives have stepped up to raise money for Krupa, although he’s raised only $8K so far and has over $5K in the bank, compared to Quinn’s $110K raised and under $99K on hand. Krupa has his own issues with women as well. Quinn may be under investigation, but he’s still a Democrat, and should win re-election against Krupa.
- David Moore (17th Ward; Auburn Gresham; Englewood; Chicago Lawn; Marquette Park; West Englewood). Moore is a progressive with something of a temper, having had domestic violence allegations in his past as well as holding up a city appointment of his predecessor, Latasha Thomas. Nonprofit manager Raynetta Greenleaf is his sole challenger. She has not raised anything, so Moore should get a second term.
- Derrick Curtis (18th Ward: Ashburn; Auburn Gresham; Chicago Lawn; North Beverly; Scottsdale; Wrightwood). Curtis is probably the most anonymous member of the Council; he’s the only member to not have a website who was elected in a regular election and the only story I could find on him was about his delinquent property taxes. Chuks Onyezia, who came in third in the 2015 race (and who managed then-incumbent Lona Lane’s unsuccessful runoff campaign against Curtis) is running again. Curtis does have more money (over $66K vs. Onyezia’s $4K) but I predict that Onyezia will pull off the upset here.
- Matt O’Shea (19th Ward; Beverly, Mount Greenwood). O’Shea’s politics reflect this white working-class ward: economically liberal (but not too far left), and socially conservative. David Dewar, who appears to be a Republican from what little information is available about him, is his sole opponent who has raised no money. O’Shea should win re-election in a walk.
- Silvana Tabares (23rd Ward; Garfield Ridge). Tabares was appointed 23rd Ward Alderman last summer after long-serving incumbent Michael Zalewski decided to retire (his son, Michael Jr., is a state representative). Tabares was also a State Representative and is running for a full term. Her sole challenger is Paulino Villarreal Jr., who is in private security. As Villarreal Jr. has not raised any money, Tabares should win this race without any trouble.
- Walter Burnett Jr. (27th Ward; West Loop; Greektown; East Garfield Park; Near North Side; Old Town; West Humboldt Park; West Town; Goose Island; Illinois Medical District). An establishment Democrat and Rahm loyalist, Burnett Jr. represents a ward that includes thriving parts of the city (West Loop) and not-so-thriving parts of the city (East Garfield Park). Real estate broker Cynthia Bednarz is challenging him. As she only raised $5K last quarter and has less than $500 on hand, Burnett Jr. (who raised $200K last quarter and has $636K on hand) should skate to re-election.
- Carrie Austin (34th Ward: Morgan Park; Roseland; Washington Heights; West Pullman). The powerful Budget Committee Chairwoman faces only one challenger for her re-election: attorney Preston Brown Jr. Brown has loaned himself some money for his campaign ($9K), but it won’t be enough to compete with Austin’s slightly larger campaign warchest (over $55K on hand).
- Carlos Ramirez-Rosa (35th Ward: Albany Park; Avondale; Hermosa; Irving Park; Logan Square). Ramirez-Rosa has had a tumultuous four years in office; he was one of the first two openly gay Latino Alderman on the Council, but unlike machine ally Raymond Lopez, he’s a stalwart progressive (and the only DSA member on the Council). However, his attempts to move up in politics have backfired; he lasted a week as State Senator Daniel Biss’s running mate before being dumped from the ticket over his views on the Israeli-Palestinian conflict. He also briefly ran for Congress after Luis Gutierrez decided to retire, although he withdrew and endorsed eventual primary winner Jesus “Chuy” Garcia. He’s running for a second term against Amanda Yu Dieterich, a small business owner whose husband happens to be Mayor Emanuel’s Deputy Budget Director. Yu Dieterich outraised Ramirez-Rosa last quarter, and Ramirez-Rosa has just over $100 more on hand than her. However, Ramirez-Rosa has done a decent job in office despite his setbacks, and I think he’ll get the victory on Tuesday.
- Anthony Napolitano (41st Ward: Edison Park, Elmwood Park). The only Republican on the Council, Napolitano relied on union support (including CTU) to unseat Democratic incumbent Mary O’Connor in 2015. The Democratic Ward Committeeman, Tim Heneghan (who, like Napolitano, is a firefighter) is challenging him for re-election. Napolitano has raised more money than Heneghan ($29K vs. $15K and $23K on hand vs $9K on hand respectively), but Heneghan should be able to put up a fight. The 41st Ward is conservative relative to Chicago, but still voted for Clinton in 2016; however, I think Napolitano has a slight edge in a low turnout election.
- Harry Osterman (48th Ward: Andersonville, Edgewater, Uptown). Osterman ran unopposed in 2015, and while he has an opponent this time the result will likely be the same. That opponent, David Earl Williams III, is a veteran and Ron Paul acolyte who ran unsuccessfully for IL-09 a couple cycles ago (he didn’t make it out of the primary). Williams has under $6K on hand, but that won’t be enough to unseat Osterman.
- Joe Moore (49th Ward; Rogers Park). Moore started his career as a progressive gadfly but became an Emanuel loyalist in recent years. Rogers Park has always been a progressive stronghold, and progressives are going all in for challenger Maria Hadden, the executive director of a nonprofit. While Moore has significantly outraised Hadden ($130K and $128K on hand vs. $50K and $34K on hand), there’s a lot of energy from the Hadden campaign, and I think she pulls off the victory here, becoming the first non-white lesbian member of the City Council in the process.
As for the other 29 wards…
- 5th Ward (South Shore and Hyde Park): Long-serving incumbent Leslie Hairston occupies an odd space on the Council as a member of the Progressive Caucus who was endorsed for re-election in 2015 by Rahm Emanuel. Hairston has two challengers running to her left: activist William Calloway, who helped to expose the LaQuan McDonald video to the world (and who ran unsuccessfully for State Representative last year) and journalist Gabriel Piemonte. While both could activate the activist vote to defeat Hairston, neither has much money on hand, so I predict Hairston wins re-election without a runoff.
- 6th Ward (Chatham; Englewood; Park Manor): Progressive Roderick Sawyer holds the seat his late father Eugene once held. He has two challengers: pastor Richard Wooten and businesswoman Deborah Foster-Bonner. Sawyer raised over $90K last quarter which is more than his two opponents combined; he should get another term.
- 7th Ward (South Shore; South Chicago; Calumet Heights; South Deering): Incumbent Alderman Gregory Mitchell unseated appointed incumbent Natashia Holmes in 2015. He hasn’t really done much in the past four years and is being challenged by two activists: Charles Kyle and Willie Wilson-endorsed Jedidiah Brown. Brown has raised about $10K and has $5K on hand; I was unable to find any fundraising numbers for Kyle. Mitchell has raised over $40K and has over $90K on hand; I think he should be fine for re-election.
- 8th Ward (South Shore; Chatham; Calumet Heights; Pullman; Avalon Park; Burnside; South Chicago): Incumbent Michelle Harris, an ally of Emanuel and chair of the powerful Council Rules Committee, is running for re-election. She has three challengers: educator and activist Jewel Easterling-Smith, NIMBY Linda Hudson, and barber Faheem Shabazz. None of her challengers have really raised anything, so Harris should cruise to re-election.
- 9th Ward (Chatham; Roseland; Pullman; West Pullman; Washington Heights; Riverdale): Incumbent Anthony Beale, another Emanuel loyalist, is seeking re-election against three challengers. They are: community organizer Cleopatra Watson, police officer Paul Collins, and education advocate Essie Hall. Watson and Hall have not raised any money; Collins has over $9K in the bank, which pales in comparison to Beale’s $101K. Beale should win re-election handily.
- 12th Ward (Brighton Park; McKinley Park; Little Village): Incumbent George Cardenas has moved left during his fourth term, although it may not be enough to save him from defeat. Three candidates are challenging him: union organizer Pete DeMay (who ran as a write-in in 2015), child care professional Martha Rangel, and educator Jose Rico. Of the three challengers, only Rico has raised any money, but he only has over $600 left on hand. Cardenas has over $200K on hand. I think he’ll ultimately win a fifth term but will face a runoff with Rico.
- 14th Ward (Archer Heights; Garfield Ridge; Brighton Park): Incumbent Alderman Edward Burke’s fifty-year tenure on the City Council looks like it’s about to come to an end after he was indicted for shaking down a local real estate developer. Progressives (led by Congressman Jesus “Chuy” Garcia) were already targeting the avatar of Chicago’s political establishment for defeat; with his legal woes said defeat is all but certain. Burke has two challengers: attorney Jaime Guzman and engineer Tanya Patiño, who has Garcia’s support and is the boyfriend of Aaron Ortiz, who unseated Burke’s brother Dan as State Representative last year. Patiño has more money on hand than Guzman ($16K vs. $12K) although they both trail Burke’s cash on hand (over $2 million). However, money probably won’t save Burke this time, and I predict that Tanya Patiño will be the next Alderman for the 14th Ward.
- 15th Ward (West Englewood; Brighton Park; Back of the Yards; Gage Park): Raymond Lopez made history in 2015 when he parlayed his role as Ward Committeeman into election as one of two openly gay Latino Alderman to the City Council. He defeated the more progressive police officer Rafael Yanez in a runoff, who is seeking a rematch with the incumbent. Also running are Some Dude Joseph Williams, community organizer Berto Aguayo, and Otis Davis Jr., director of the “New City Holistic Community Development Project”. I’m predicting another Lopez-Yanez runoff since they’re the only two candidates who have really raised money; my guess is that Lopez gets a second term in April.
- 16th Ward (Englewood; Gage Park; West Englewood; Chicago Lawn): Toni Foulkes is one of the most progressive members of the Council, and one of the more anonymous members (despite a proud history of organizing). Redistricting in 2015 forced her out of her 15th Ward into the 16th Ward against establishment Alderman JoAnn Thompson; however, Thompson died of complications from heart surgery on the first day of early voting. Foulkes ended up in a runoff with Stephanie Coleman, daughter of Thompson’s predecessor on the Council. Coleman is seeking a rematch with Foulkes, along with four other candidates: building inspector LaTasha Sanders, Kenny Doss II, a basketball star at tiny D-III Manchester College, Some Dude Jeffrey Lewis, and educator Eddie Johnson III (no relation to the current police chief). Foulkes and Coleman are the only candidates to have raised any money, and I predict they will end up in a runoff again that Foulkes (who has over $36K on hand to Coleman’s $6K) will win.
- 20th Ward (Woodlawn; Englewood; Back of the Yards; Greater Grand Crossing): Under indictment, incumbent Alderman Willie Cochran decided to not seek re-election, setting off a crowded race to succeed him. Nine candidates made the final ballot: activist and Chairperson of the Mollison Elementary Local School Council Jeanette Taylor, third grade math teacher Nicole Johnson, CHA project manager Maya Hodari, police officer Jennifer Maddox, welder Andre Smith, attorney and pastor Dernard Newell, HR professional Quandra Speights, civil engineer and Democratic Ward Committeeman Kevin Bailey (who went to a runoff with Cochran in 2015), and young public policy professional Anthony Driver. There will almost certainly be a runoff here; based off fundraising I’d say Johnson (over $36K on hand) and Bailey (over $18K on hand) will advance, but don’t count out Taylor (who progressives are backing), Hodari (who has the newspaper endorsements), Maddox, or Smith.
- 21st Ward (Auburn Gresham; Washington Heights; Chatham; Roseland): I’m surprised incumbent Alderman Howard Brookins Jr.—an ally of Rahm Emanuel—is running for re-election, given his frequent bids for higher office in recent years (running unsuccessfully for IL-01 in 2016 and for a judgeship in 2018). Nevertheless, he’s facing off against three challengers on Tuesday: 2015 runoff opponent Marvin McNeil, Department of Public Health Administrative Assistant Patricia Foster, and insurance agent Joseph Ziegler, Jr. None of the challengers have raised much money, so it looks like Brookins Jr. will win re-election, either on Tuesday or in the runoff.
- 22nd Ward (Little Village): progressive incumbent Rick Munoz is retiring, albeit in disgrace, since he was arrested for domestic violence on New Year’s Eve. Four candidates are running to succeed him: Ward Committeeman and Executive Officer of the Cook County Medical Examiner’s Office Michael Rodriguez, social worker Liz Lopez, nonprofit employee Richard Juarez, and Some Dude Neftalie Gonzalez. Only Rodriguez has raised any money, so he’ll likely be the next Alderman for the 22nd Ward, probably without a runoff.
- 24th Ward (North Lawndale): Incumbent Michael Scott Jr. is running for a second term. He has three challengers: businessman Creative Scott, dogtrainer Toriano Sanzone, and activist Treasure Johnson. Only the incumbent has raised any money, and he should win re-election comfortably.
- 25th Ward (Pilsen): Incumbent Alderman Danny Solis, an Emanuel ally, shocked the Chicago political world when he announced his retirement right before the filling deadline. In hindsight, it makes sense why: he wore a wire to record conversations with fellow Alderman Ed Burke to help the Feds with their case against Burke, in large part because the Feds had evidence that Solis misspent campaign funds for personal expenses. Since then, he’s disappeared from public life entirely. The 25th Ward, which also includes parts of the South Loop and Chinatown, will have new representation soon enough in the form of one of five candidates running to succeed Solis. They are: teacher and organizer Hilario Dominguez, pediatric nurse Alex Acevedo, data scientist Troy Hernandez, Executive Director of the Pilsen Alliance Byron Sigcho-Lopez (who almost forced a runoff with Solis in 2015), and principal Aida Flores. The establishment is backing Acevedo, progressives are backing Sigcho-Lopez, and EMILY’S List is backing Flores. I would bet that one of those three candidates will be the next Alderman. Based on fundraising I’d pick Sigcho-Lopez (who I should note approached me to work on his 2015 campaign; nothing came of it); he raised $31K last quarter and has over $40K on hand. However, don’t count out Flores ($40K raised, $32K on hand), or Acevedo (over $50K raised, $27K on hand). Heck, even Dominguez has a shot ($26K raised, $21K on hand), but not Hernandez ($310 raised, $8K on hand).
- 26th Ward (Humboldt Park; Logan Square; Hermosa; West Town): Rahm ally Roberto Maldonado is seeking re-election in this Northwest Side ward. He faces two challengers: healthcare entrepreneur Theresa Siaw and former banker David Herrera. Siaw has outraised Maldonado ($154K to $8.6K) and has way more on hand ($100K to under $42K), while Herrera has raised nothing. Maldonado does have machine support, so I wouldn’t count him out, but don’t be surprised if Siaw pulls off the upset here.
- 28th Ward (West Garfield Park; South Austin): Incumbent Jason Ervin (whose wife Melissa is running for City Treasurer) is seeking re-election in this West Side ward. He ran unopposed in 2015 but has three challengers this time: computer engineer Miguel Bautista, educator Jasmine Jackson, and nurse practitioner Beverly Miles. Miles has raised the most of the three, but still trails Ervin in fundraising by a wide margin ($7.7K to his $151,400). Ervin is favored, but if Miles or another opponent can effectively highlight his ties to Emanuel he could be forced into a runoff. That’s unlikely, given his opponents’ poor fundraising.
- 29th Ward (Austin; Montclare; Galewood): Police officer Chris Taliaferro unseated Machine incumbent Deborah Graham in 2015. A progressive, he faces two challengers in his re-election bid: Dwayne Truss, a tax auditor for the State of Illinois, and activist Zerlina Smith. Neither Truss nor Smith has raised much money for their bids, so Taliaferro shouldn’t have anything to worry about for his re-election.
- 30th Ward (Belmont Cragin; Kilbourn Park): After running unopposed in 2015, Emanuel ally Ariel Reboyras faces two challengers for his re-election in 2019. Only one of those challengers is serious: Jessica Gutierrez, an organizer who is the daughter of former Congressman Luis Gutierrez. Student Edgar “Edek” Esparza is also running, but his website is among the nastiest I’ve ever seen (very few things about him and what he would do, mostly just attacks on Reboyras and Gutierrez). Esparza has raised about $4K, which is nowhere near what his opponents have (both have over $100K on hand) but could be enough to force a runoff between Reboyras and Gutierrez. Regardless, I think momentum is on Gutierrez’s side, and that she will continue her father’s progressive legacy by unseating Reboyras.
- 31st Ward (Hermosa): Milly Santiago, a former journalist, unseated incumbent Ray Suarez in the 2015 runoff here. She’s being challenged for re-election by two opponents: automotive analyst/community organizer Colin Bird-Martinez and Felix Cardona Jr., an employee of the Cook County Assessor’s office. Cardona Jr. raised the most money last quarter (over $32K) but Santiago has over $69K on hand. If there is a runoff, I can see it being between Cardona Jr. and Santiago, but I think Santiago is favored to win a second term.
- 33rd Ward (Avondale, Albany Park, Irving Park): The first lesbian member of the Illinois General Assembly, Deborah Mell became the first (and to date only) lesbian member of the City Council when she was appointed in 2013 to replace her father, long-serving Alderman Richard Mell. (Richard’s daughter and Deborah’s sister, Patti, married disgraced former Governor Rod Blagojevich, whose political rise Mell was responsible for.) The younger Mell barely avoided a runoff in 2015 for a full term; her 2015 opponent, high school history teacher Tim Meegan, has since moved out of state. Mell has two challengers for her 2019 re-election: businesswoman Katie Sieracki and teacher Rossana Rodriguez-Sanchez. Sieracki has the Chicago Tribune endorsement, while Rodriguez-Sanchez has the backing of much of the city’s progressive and leftist groups and politicians. While Mell laps the field in fundraising ($96K raised last quarter, $217K on hand), Rodriguez-Sanchez does have enough money to hold her own ($34K raised, $44K on hand). I’m predicting a runoff this time, although I think Mell narrowly escapes defeat again in April.
- 37th Ward (Austin; West Garfield Park; West Humboldt Park): Incumbent Emma Mitts is a creature of the Machine and was forced into a runoff in 2015 against progressive teacher Tara Stamps (daughter of legendary civil rights activist Marion Stamps). Stamps is seeking a rematch, along with Some Dude Deondre’ Rutues. Neither challenger has raised money, so Mitts should get another term, likely without a runoff this time.
- 39th Ward (Edgebrook; Forest Glen; Mayfair; Sauganash): Incumbent Alderman Margaret Laurino is retiring after twenty-five years on the Council. Four candidates are vying to succeed her: architect and Ward Committeeman Robert Murphy, Director of Executive Engagement for the American Board of Medical Specialties Samantha Nugent, Director of Individual Giving and Community Engagement for the Albany Park Community Center Casey Smagala, and police officer Joe Duplechin. Duplechin hasn’t raised much compared to the other three candidates, who raised similar amounts last quarter ($25K for Nugent, $23K for Murphy, and $20K for Smagala). However, Nugent has the most on hand ($111K) compared to Murphy ($57K) and Smagala ($27K). My guess is that we’ll see a Nugent-Murphy runoff, and that Murphy, after falling short of forcing a runoff with Laurino in 2015, will get to be Alderman for the 39th Ward.
- 40th Ward (Ravenswood; Budlong Woods; West Ridge; West Edgewater; Andersonville): Patrick O’Connor is the second-longest tenured member of the City Council, who serves as Mayor Emanuel’s floor leader. After attracting one challenger in 2015, he faces four challengers this time: organizer and Evanston City Clerk employee Ugo Okere, teacher and 2015 challenger Dianne Daleiden, manager Andre Vasquez, and political staffer Maggie O’Keefe. There seems to be a genuine desire for change in this diverse ward, and I think a runoff is likely. My guess is that Vasquez (who has raised the most money of O’Connor’s challengers) advances, although I think O’Connor will ultimately prevail in April.
- 43rd Ward (Lincoln Park): Michele Smith has never had an easy time winning this wealthy ward; in both of her two prior elections, she was forced into a runoff, and won the 2015 runoff by just 79 votes. She faces five challengers this time: former Emanuel policy advisor Derek Lindblom, public relations professional Leslie Fox, consultant Jacob Ringer, video producer Steven McClellan, and attorney and former Toni Preckwinkle counsel Rebecca Janowitz. Smith raised the most money last quarter ($159K), but trails Lindblom in cash on hand ($275K to her $258K). I’d bet on a Lindblom-Smith runoff, although I wouldn’t count out Fox or Ringer. I also think the third time will be the charm for Smith’s challengers, and that Lindblom will prevail over Smith in the April runoff.
- 44th Ward (Lakeview; Boys Town): Incumbent Tom Tunney was the first openly gay member of the City Council but is facing his toughest re-election battle yet. Tunney happens to represent Wrigley Field, and has pushed back against Cubs ownership’s attempts to redevelop the area around the legendary ballpark. As a result, the conservative Ricketts family (which includes Nebraska GOP Governor Pete) is funding challengers to Tunney: businessman and former policy advisor Austin Baidas, and consultant Elizabeth Shydlowski. Baidas has outraised Tunney ($361K to $235K), but Tunney leads in cash on hand ($355K to $288K). My guess is that Baidas forces a runoff, but Tunney (with both progressive and establishment support) gets a fifth term on the Council.
- 45th Ward (Portage Park; Gladstone Park; Mayfair; Edgebrook; Forest Glen; Jefferson Park): John Arena won this Northwest Side Ward in 2011. As an outspoken progressive, he’s been frequently targeted for defeat, and 2019 is no exception, considering his advocacy for affordable housing in his ward. He faces three challengers this cycle: park district administrator Marilyn Morales, teacher/firefighter Jim Gardiner (who was just accused of stalking), and NIMBY Bob Bank. Of the three challengers, Gardiner has raised the most and has the most cash on hand ($30K and $19K respectively). Arena faced close runoffs in 2011 and 2015 with Republican police officer John Garrido; Gardiner should force a runoff, but I think Arena will prevail once again.
- 46th Ward (Uptown): James Cappleman succeeded the great Helen Shiller in 2011, becoming the second openly gay member of the Council. An ally of Emanuel, he faces five challengers this cycle: scientific research consultant Marianne Lalonde, teacher Erika Wozniak Francis, Public Allies Chicago Program Director Justin Kreindler, activist Angela Clay, and political staffer Jon-Robert McDowell. Wozniak Francis has raised the most money ($29K) of Cappleman’s challengers, but Lalonde has the most money on hand ($37K). One of them will advance to a runoff with Cappleman, but my guess is that Cappleman will prevail again in April.
- 47th Ward (Ravenswood; North Center): Incumbent Ameya Pawar is running for City Treasurer, setting up a nine-candidate race to succeed him. The candidates are: social worker Eileen Dordek, music teacher Angie Maloney, manager of neighborhood relations for the Chicago Cubs Heather Way Kitzes, Emanuel aide Michael Negron, civil rights attorney Matt Martin, restaurant owner Gus Katsafaros, firefighter Tom Schwartzers, psychiatrist Kimball Ladien, and circus nonprofit founder Jeff Jenkins. With such a large field for an open seat, there will be a runoff. The two best fundraisers are Negron ($114K, $212K on hand) and Dordek ($70K, $208K on hand), but I wouldn’t count out Way Kitzes ($21K, $39K on hand), Martin ($49K, $71K on hand), or Jenkins ($29K, $21K on hand).
- 50th Ward (West Rogers Park): Incumbent Debra Silverstein’s had a rough year or so after her husband Ira lost his State Senate seat over allegations of sexual harassment. She faces two challengers in her bid for a third term: educator Andrew Rowlas (who is endorsed by the Green Party amongst others) and nonprofit director Zehra Quadri. Neither have raised much money compared to the incumbent, who should get her third term with ease.
Feel free to ask questions in the comments below! Thank you for reading, and I’m looking forward to watching the returns on Tuesday night! Polls close at 7 CDT (8 EDT). If you live in Chicago and haven’t voted yet, be sure to do so on Tuesday!
