Clockwise from top-left: Cook County Board President Toni Preckwinkle and her challenger Richard Boykin; Assessor Fritz Kaegi and his challenger Kari Steele; Board of Review Comm. Tammy Wendt and her challenger Chicago Ald. George Cardenas (12) [Facebook]

Midterm elections can be low-profile affairs in Chicago, especially without a competitive gubernatorial primary at the top of Democratic ballots. But Tuesday’s election will mark a critical juncture for Cook County, offering a referendum on its controversial public safety strategy and its messy tax assessment regime.

Some powerful county executives, like county Clerk Karen Yarbrough, Treasurer Maria Pappas and Board of Review Comm. Larry Rogers (D-3), will face no competition in the polls this week. Neither will 10 of the 14 incumbent Cook County commissioners who are running for reelection.

Still, the range of competitive races could set the stage of a potential Republican resurgence on the Cook County Board of Commissioners. And the results will offer the latest indication of the Cook County Democratic Party’s power to swing races up and down the ballot.

President 

In her first return to the campaign trail after her landslide defeat in the 2019 runoff race for Chicago mayor, Cook County Board President Toni Preckwinkle is vying for her fourth consecutive term as the top executive in county government. If the 75-year-old former social studies teacher and longtime Chicago alderman cruises to reelection as expected, she will become the longest-serving person to hold the position since George Dunne, who held the role from 1969 to 1990. 

But first, she will have to dispatch Democratic challenger Richard Boykin. Boykin has been a thorn in Preckwinkle’s side since at least 2017, when as a Cook County commissioner he led a successful push to spike the president’s maligned penny-per-ounce sweetened beverage tax. 

Related: County Finance Committee Votes to Repeal Beverage Tax 15-1; Heavy Budget Lift Begins ASAP 

Preckwinkle took her revenge in 2018 by backing Chicago Teachers Union organizer Brandon Johnson’s primary campaign that ran Boykin out of office. Boykin has repeatedly found his way back into the limelight, including as a spokesperson for perennial Chicago mayoral candidate Willie Wilson and as a candidate in 2020 for Cook County Circuit Court Clerk. He finished third in that four-way race, finishing behind then-Sen. Iris Martinez (D-Chicago) and Board of Review Comm. Michael Cabonargi (D-2). 

Preckwinkle has rarely missed an opportunity to tout the county’s vastly improved finances since she took over the role in 2011, and she has presided over grinding efforts to both reduce the population of the county’s jail and root out its decades-old legacy of political patronage. But like many incumbents at the state and local level, she has also struggled to account for historically high rates of violent crime.  

Boykin has seized on the opening relentlessly, blaming the county’s 2020 resolution to shift resources from policing to social services as “pandering to the…‘defund the police’ movement” and citing it as a reason for the surging crime. Preckwinkle has shrugged off the attack, pointing to the tens of millions of dollars the county is pouring into street-level outreach and other non-police anti-violence methods she argues are more effective public safety strategies. 

Preckwinkle, who chairs the Cook County Democratic Party, maintains a campaign financing juggernaut. She reported nearly $343,000 on hand at the end of the last reporting period in March and has since reported tens of thousands more in donations from a wide range of donors including unions, attorneys, businesspeople and political allies. On June 16, Gov. JB Pritzker cut her campaign a $100,000 check, election records show. 

However, Boykin, who is a practicing attorney, has raised more than enough money to wage a competitive countywide campaign. He reported $70,837 on hand on March 31 and has since racked up dozens of checks of $1,000 or more, including $100,000 in contributions from Wilson since May 19. He raised eyebrows when he reported campaign donations from many of the gas station owners who facilitated Wilson’s multiple gasoline donations this spring. 

Promoted Event: The Press Box

Assessor 

Fritz Kaegi was an insurgent outsider when he ran to oust Assessor Joseph Berrios, then chair of the Cook County Democratic Party, from office in 2018. Four years later, Kaegi is the incumbent leaning on the party’s backing to fend off a challenger who argues he has failed in his campaign promise to bring accuracy and professionalism to the office charged with valuing properties to calibrate their property tax bills. 

Through three separate tax assessment years, Kaegi has pushed to radically shift the county’s property tax burden away from homeowners and toward the owners of larger commercial buildings, whom Kaegi argues got unfair advantages under Berrios. But the shift sparked a seismic backlash from the Chicago-area real estate industry, saying his policies have cranked up the power on already brutal headwinds flying in the faces of landlords and investors. 

Related: Kaegi touts skew of assessments toward downtown businesses in reelection closing argument 

Real estate groups like the Building Owners and Managers Association of Chicago and the Chicagoland Apartment Association have poured tens of thousands of dollars into the campaign of Metropolitan Water Reclamation District President Kari Steele. She has posed her decade-long record of competent management at the district as a contrast to the barrage of headlines that have hounded Kaegi, from his controversial “COVID adjustment” that delayed taxes and gave excessive breaks to homeowners last year to his office’s miscalculation of senior exemptions. 

Related:  

• Steele pounces on ‘backfired’ COVID assessment breaks as Kaegi sticks by controversial 2020 decision
• Kaegi defends overhauling reassessments on short deadline: ‘We don’t have a lot of great choices’

But more recently, Kaegi’s campaign has found opportunities to go on offense by drawing letters from multiple coalitions of powerful Democrats scolding bigotry on her husband Maze Jackson’s radio show. They have also pointed to reporting showing that Steele has received an improper homeowner exemption on her home. 

Steele has raised formidable cash, in large part due to support from the real estate industry. But Kaegi, who was previously a financial asset manager, has kept a decisive cash advantage by feeding nearly $2 million into his own campaign and by scoring six-figure checks from prolific donors Joe Mansueto and Fred Eychaner. 

Board of Review 1st District 

Property tax attorney Tammy Wendt, whose only previous public exposure in 2020 had been her role as a defense attorney for Chicago Police Officer Jason Van Dyke, scored back-to-back upsets when she edged out party-endorsed primary opponent Abdelnasser Rashid and then incumbent Cook County Board of Review Comm. Dan Patlak (R-1). But after two years of making enemies in nearly every corner of county government, Wendt faces an even steeper climb to reelection. 

Wendt, who has voted in multiple Republican primaries and has declined to say whether she voted for President Donald Trump, rankled Cabonargi and Rogers as soon as she took office and brazenly broke county ethics rules by hiring her first cousin Todd Thielmann as her chief of staff. 

State lawmakers came to Cabonargi’s and Rogers’ defense last year when they redrew the Board of Review’s election map to obliterate Wendt’s mostly suburban 1st District, slipping her Palos Heights home into a new majority-Latino district that stretches into Chicago’s Pilsen neighborhood. That created an opening for Chicago Ald. George Cardenas (12), who mounted a challenge highlighting Wendt’s ethics violation and promising to bring order and fairness to the board. The Cook County Democratic Party took the rare step of endorsing the challenger in the race when it backed Cardenas last December. 

Related:  

•  New Board of Review boundaries reshuffle Latino voters, lock in 3 safe Dem districts
•  Dems back Cardenas for Board of Review, turning on ‘disaster’ Wendt while backing other incumbents 

With the backing of the Fraternal Order of Police and a smattering of suburban mayors, Wendt posted $41,509 in her campaign account on March 31 and $5,500 in large donations since. Cardenas holds a decisive cash advantage, having racked up tens of thousands of dollars in recent months — including $5,000 from Rep. Chuy Garcia (D-Ill.) — across two political committees. 

Board of Review 2nd District 

While Kaegi has steered clear of the two contested Board of Review races, many of his supporters have boosted the candidacy of Samantha Steele, a real estate appraiser and former member of Kaegi’s 2018 transition team. 

Steele, who is not related to Kari Steele, is looking to unseat Cabonargi as a reform candidate who will disrupt what she calls a pay-to-play network at the Board of Review — a similar message that delivered Kaegi victory in 2018. She points to Cabonargi’s acceptance of campaign donations from property tax attorneys and the ongoing FBI investigation into an alleged bribery scheme inside the Board of Review. 

But Cabonargi, who is well-connected and popular in local Democratic Party circles, has mounted a heavy campaign blitz including mailers and far-reaching digital advertising promoting his constituent engagement on the board. His campaign has also mounted an all-out offensive against Steele, designing an opposition research website that pointed to what it called her “failed mismanagement” during the single term she served as an Indiana assessment officer from 2006-10 and drew connections between her public actions and personal business. 

And Steele suffered a fresh setback on Monday, when her former campaign strategist Rebecca Williams filed a lawsuit aiming to recoup more than $14,000 in paychecks that Steele “fraudulently canceled.” 

Cabonargi has dominated the money race, reporting $134,341 on hand on March 31 with tens of thousands of follow-up contributions during the spring. Steele lags far behind, having posted less than $10,000 on hand in March with $4,000 in large donations posted since. 

Sheriff 

Although incumbent Cook County Sheriff Tom Dart drew three Democratic primary challengers this year, his toughest competition has already played out behind the scenes in courtrooms and Board of Elections hearings, setting the stage for him to waltz to a fifth term overseeing Cook County’s jail and its staff of court bailiffs and auxiliary police. 

Chicago Police Sgt. Noland Rivera and longtime deputy sheriff LaTonya Ruffin mounted longshot bids for the office, saying their law enforcement backgrounds qualified them to crack down on spiraling violence. But the most powerful challenge came from Carmen Navarro Gercone, who served 26 years in the Sheriff’s office before becoming a senior member of Cook County Circuit Court Clerk Iris Martinez’s leadership team. Martinez, who is also 33rd Ward Democratic committeeperson, came out in support of Gercone’s candidacy, giving her a significant boost. 

Related: Kaegi, Dart set for Dem party endorsements in incumbent-friendly slating session as ‘loyalty pledge’ comes under fire 

However, Dart’s campaign pushed election officials to knock Gercone from the ballot because she was out of compliance with a state law requiring candidates for sheriff to obtain law enforcement certifications. Gercone’s campaign sued and got the ruling it sought from a circuit judge who ordered her back onto the ballot — only for an appellate court to overturn the ruling and bounce her out of the race for good earlier this month. 

Dart’s attorneys also managed to knock Ruffin off the ballot with a challenge to her signature petitions, leaving Rivera as his only remaining primary challenger. Rivera reported nearly $80,000 in his campaign account on March 31, with $12,000 in large donations since. Dart reported $531,121 on hand at the end of March, followed by $29,000 in reportable contributions since. 

Board of Commissioners 5th District 

The retirement of veteran Cook County Comm. Deborah Sims (D-5) set up an open-seat battle exposing the generational and political divide cleaving Chicago’s Far South Side and south suburbs. 

Sims tossed her support behind Monica Gordon, who is director of government affairs and community relations at Chicago State University. A parade of local political leaders followed, including Chicago Ald. Anthony Beale (9), Sen. Napoleon Harris (D-Chicago), Rep. Justin Slaughter (D-Chicago) and more than a dozen south-suburban mayors who also backed Gordon. 

Also in the running is Hazel Crest Mayor Vernard Alsberry, who has a thinner endorsement list but carries his own substantial clout as the democratic committeeperson for south-suburban Bremen Township. 

And Jaylin McClinton, a former White House staffer and aide to then-Rep. Julianna Stratton (D-Chicago), is running with the backing of Rep. Lamont Robinson (D-Chicago) and Sen. Robert Peters (D-Chicago), plus state and national organizations including Democracy for America, Equality Illinois, Our Revolution Illinois and Personal PAC. McClinton got a boost earlier this month, when primary competitor Kierra Williams dropped out of the race and endorsed him. 

Gordon posted just $13,576 in her campaign account at the end of March but has since raised tens of thousands more, including with a $5,000 check from Rep. Marcus Evans (D-Chicago) and more than $50,000 from SEIU’s political action fund. 

Alsberry reported $95,675 on hand on March 31 and has since posted dozens of donations of $1,000 or more from attorneys, consultants and businesses, plus an $18,000 self-donation and $5,000 from Sen. Michael Hastings (D-Tinley Park). 

McClinton reported $31,621 on hand on March 31 and more than $20,000 since, including donations from Rep. Kam Buckner (D-Chicago), Chicago Ald. Jeanette Taylor (20) and Rep. Greg Harris (D-Chicago). 

8th District 

Barely a month after his father, former Rep. Luis Arroyo, Sr., was sentenced to nearly five years in prison on a corruption conviction, Comm. Luis Arroyo, Jr. is facing four primary opponents — more challengers from the same party than all his Board of Commissioners colleagues combined. 

Related: Arroyo Jr. faces army of primary challengers after father’s conviction: ‘They smell blood in the water’ 

Sensing his vulnerability, Edwin Reyes, who served as 8th District commissioner until Arroyo Jr. unseated him in 2014, is mounting a comeback on a tough-on-crime platform. Also in the race are Anthony Quezada, a Democratic Socialist organizer and longtime aide to Chicago Ald. Carlos Ramirez-Rosa (35); Rory McHale, an Irish American attorney and former deputy under Chicago Inspector General Joseph Ferguson; and Natalie Toro, a Chicago Public Schools elementary school teacher who is backed by Cook County Circuit Court Clerk Iris Martinez.  

Reyes has gone nearly toe-to-toe with Arroyo in fundraising, seeding his campaign with a $50,000 loan and padding it with $7,000 in contributions from real estate agent Mike Greco and a range of other small donors.  

As of March 31, Arroyo led the money race with $68,245 on hand. He has since claimed donations of $2,500 each from Local 134 State & Municipal Pac and Teamsters Local Union 700.  

While Quezada lagged with just under $40,000 on hand at the end of March, state campaign finance records show he has rocketed into the lead with another $38,300 in contributions of $1,000 or more from donors including Ramirez-Rosa, United Working Families and the independent political organization United Neighbors of the 35th Ward.  

McHale reported $22,328 on hand on March 31 and $17,100 in large donations since, including a $2,000 self-donation, records show.   

Toro reported no cash at the end of the first quarter, having only jumped into the race at the end of March. But she reported $6,430 in a trio of large donations since, including a $2,500 check from attorney Stephen Swedlow, who is running for Cook County Judge in the 8th Subcircuit.  

17th District 

Like Arroyo, Comm. Sean Morrison (R-17), who chairs the Cook County Republican Party, is facing a challenge from a former commissioner who wants their old seat back. 

Elizabeth ‘Liz’ Doody Gorman represented the relatively conservative all-suburban 17th District from 2002 until 2014, when she stepped down to become a consultant and endorsed Morrison as her successor. But she has since soured on the incumbent, saying he has become too divisive and antagonistic on the Democrat-dominated board. 

The Republican primary has become bitter and personal, with Gorman trying to tie Morrison to a senior employee at his security firm who was arrested in 2014 on sexual misconduct charges. Morrison has hit back by promoting a letter from the mother of the man’s victim calling Gorman’s claims “lies” and a “political smear campaign.” Morrison has also hit Gorman for having sided with Democrats on the board during her tenure, including by breaking with her fellow Republicans to vote in favor of county board President Todd Stroger’s controversial Fiscal Year 2009 budget. 

The winner of Tuesday’s primary will face the winner of a Democratic race between La Grange Village Trustee Lou Gale and former Orland Park Village Trustee Daniel T. Calandriello. 

9th District 

Comm. Peter Silvestri’s (R-9) January announcement that he will not seek an eighth term on the board set up an open race for Republicans vying to carry on his moderate legacy on the county’s Far Northwest Side and northwest suburbs. 

Related: NW Side Republicans vie to pick up Silvestri’s moderate mantle on Cook County Board 

The front-runner in the race is Matt Podgorski, a corporate logistics director who co-founded the Northwest Side GOP Club in 2016 and has counted support from Chicago Ald. Anthony Napolitano (41), former county Comm. Tim Schneider, businessman Richard Uihlein and Rep. Tim Ozinga (R-Mokena).  

Also in the race but lagging far behind in fundraising and endorsements are Mark Hosty, a real estate agent and former Forest Park village commissioner who boasts the support of House Minority Leader Jim Durkin (D-Western Springs), and security worker Frank Coconate. 

Even more crowded is the Democratic side of the race. The contenders are Maggie Trevor, a researcher and political science professor who lives in Rolling Meadows and fell 44 votes short of unseating Rep. Tom Morrison (R-Palatine) in 2018; Sam Kukadia, an environmental engineer with heavy support from organized labor; Frank McPartlin, who ran against Silvestri in 2018; and Heather Anne Boyle, a business owner who mounted an unsuccessful bid for the Metropolitan Water Reclamation District Board in 2020 and is running on a pro-police and anti-corruption platform. 

Everyone in the race has acknowledged the mostly suburban district as closely matched between Republicans and Democrats as the suburbs have trended bluer; Silvestri, who is popular, squeaked out reelection in 2018 by about 5 percentage points. However, during an election cycle when momentum favors Republicans across the country, Democrats are expected to face an uphill climb in the race. 

2nd District 

Comm. Dennis Deer (D-2) was appointed to replace former Comm. Robert Steele as the representative of Chicago’s Near South Side and West Side on the board, and Deer earned a term of his own after defeating four primary opponents in 2018. He chairs the Board of Commissioners’ Health & Hospitals Committee and sits on the Cook County Health Board of Directors. 

Deer faces a challenge from Andre Smith, an anti-violence organizer who failed to make the runoff in the open race for Chicago’s 20th Ward alderman in 2019. Smith lags far behind in endorsements in fundraising, having reported less than $400 on hand on March 31. He has since logged $4,000 in large donations — all from Boykin. 

16th District 

Comm. Aguilar (D-16) is asking voters in Chicago’s majority-Latino western suburbs to elect him to a full term on the Board of Commissioners two years after local party leaders met behind closed doors and picked him to replace former Comm. Jeffrey Tobolski, whose McCook office had been raided by the FBI and who would eventually plead guilty to extortion charges. 

Aguilar faces a challenge from Leticia “Letty” Garcia, a nurse who is running on a platform centered on abortion access and racial justice. 

Aguilar has claimed a healthy fundraising haul, reporting $20,479 on hand on March 31 with tens of thousands since, including $10,000 from the Cicero Voters Alliance and $2,500 from IBEW Local 134. Garcia reported $15,718 in her campaign account on March 31 and has not since reported any donations of $1,000 or more. 

Metropolitan Water Reclamation District 

Eleven candidates filed to run for four open seats on the Metropolitan Water Reclamation District of Greater Chicago, including a special two-year term to finish out the term of Comm. Debra Shore, who was tapped by President Joe Biden last year to head up the Midwest regional office for the U.S. Environmental Protection Agency. Gov. JB Pritzker appointed Chakena Perry to fill the vacancy, and Perry is asking voters to keep her on the board. But Cook County Democrats instead endorsed Daniel Pogorzelski, a longtime aide to Illinois Treasurer Michael Frerichs and Sen. Robert Martwick (D-Chicago), to fill the slot.   

The party also endorsed incumbent Comm. Mariyana Spyropoulos for a third six-year term on the board. And they picked Matteson Village Clerk Yumeka Brown and Crestwood Village Trustee Patricia Theresa Flynn to take the place of retiring reclamation board Comm. Barbara McGowan and Comm. Josina Morita, who is running unopposed to succeed Comm. Larry Suffredin (D-13) on the county Board of Commissioners. 

However, 83-year-old civil engineer Frank Avila, Sr., who was ousted from the board in 2020 after 18 years of service when the party dumped him from its slate, is mounting a comeback. Avila is heading up a slate of candidates including Rick Garcia, Cristina Nonato and Elizabeth Joyce, saying their group is more experienced and diverse than the party-backed lineup. 

Related: Crowded Water Reclamation District race emerges as insurgent slate looks to take on party picks 

Also in the running are Precious Brady-Davis and Sharon Waller. 

Judges 

With 75 candidates running for two appellate court openings, 10 circuit court vacancies and 15 judicial subcircuits, voters face a dizzying array of options — even as a historically small crowd of candidates asks to be put on the bench. 

The results will be a test of how much power the Cook County Democratic Party still holds in down-ballot races, where sitting Chicago alderman and Democratic committeeperson Howard Brookins (21) is running as part of the party-endorsed slate. Voters can also turn to Injustice Watch for a thorough guide into the platforms and ratings of every judicial candidate. 

CloutCast: Injustice Watch’s Jonah Newman on how to vote for judges