The mayoral primary is still 11 months away (February 28, 2023), but it’s not too early to start ranking the potential candidates according to their chances of victory. In general, it’s never too early to talk about politics in Chicago. Chicago is to politics as Paris is to romance, as the saying goes. This is one of the rare mayoral elections in which the incumbent doesn’t start out as the favorite. With no previous experience in elected office, Lori Lightfoot has become one of the least popular mayors in Chicago history, blamed for a rising murder rate and for her inability to build alliances with aldermen. That means she’ll have plenty of challengers, and we’ll have plenty of candidates to rank. Look for this feature at least once a month until the election.
1. Mike Quigley
Rep. Quigley is polling voters for a potential mayoral run, in which he (along with every other candidate) will attack Lightfoot for failing to keep Chicago safe. According to Crain’s Chicago Business, the poll “had about 20 questions and is heavy on queries about crime, asking about Lightfoot’s record as mayor and Quigley’s efforts to fight crime in Congress and earlier as a Cook County commissioner.” Congressman is good preparation for mayor — Harold Washington and Rahm Emanuel both held that office — and Chicago is one of the few cities where a congressman is less important than the mayor. So this would be a promotion for Quigley. What will make him a tough opponent for Lightfoot is the fact that his congressional district overlaps the North Side progressive wards that put the mayor in the runoff in 2019. (While we’re on the subject of congressmen, Chuy Garcia has disclaimed interest in running for mayor, but will go to the top of the power rankings if he does.)
2. Lori Lightfoot
She has the biggest dick in Chicago. She has 70 cops protecting her. She called an alderman a “jackass” in a text message. Oh, and murders are at a 25-year high since she came into office. These are among the reasons only 26 percent believe Lightfoot deserves a second term, according to an Ogden & Fry poll taken last November. She keeps giving us more. Nonetheless, Lightfoot is the incumbent — “an incumbent mayor with a national reach,” as she puts it — which makes it possible for her to fly around the country and raise money in Miami and Washington, where she’s more popular than she is in Chicago. (Still, she only had $1.56 million on hand in January. That’s how much Rahm Emanuel tips his Uber driver.) Although Lightfoot got to the mayor’s office with the support of lakefront liberals, she is now most popular in the Black community, which feels that “this is probably the last shot to have a Black mayor, because of the declining population,” according to radio host Maze Jackson. You have to think Lightfoot would at least make the runoff before becoming the first elected mayor since Jane Byrne to be voted out of office.
3. Paul Vallas
Vallas has been running for mayor almost since he got 5 percent of the vote in the 2019 primary. He’s been attending “Back the Blue” rallies and has called police superintendent David Brown’s antiviolence strategy of dispatching a roving antigang unit to various parts of the city “an epic failure.” It’s a law-and-order strategy to appeal to a crime-weary city, although he would never use that loaded term. Since Arne Duncan announced he won’t be running, Vallas has the “technocrat who’s never been elected to anything” lane to himself. Vallas is full of ideas, but his failures as a campaigner go back 20 years, when he lost the 2002 Democratic primary for governor by 25,000 votes to the more hirsute, more charming Rod Blagojevich. Bet you wish you’d voted for him then. Blago would be a forgotten congressman instead of a Cameo celebrity, and Vallas wouldn’t be running for mayor, waving a broom, and churning out white papers.
4. Willie Wilson
“With GOD’S Help and Wisdom We Will Get Through These Tough Times Together. Free Gas Donated By Dr. Willie Wilson. Businessman. Philanthropist. Humanitarian.” So read the banner across the street from a station that participated in Wilson’s $1.2 million gasoline giveaway. That was a stunt to promote Wilson’s third campaign for mayor, which he will announce April 11. Wilson says “crime is the number one issue,” but this identifies him as a candidate who thinks inflation and suspending the 8-cents-a-gallon gas tax are the city’s most important concerns. Wilson won 13 of 18 Black wards in the 2019 primary, and has given away most of his free gas in those communities, causing traffic jams that stretched for blocks. The city’s Black population is declining, and Wilson has never been able to sell himself to White, Latino or Asian voters. It’s hard to see him making the runoff. But he’ll give a lot of press conferences and give away a lot of money over the next year. Those are two things Willie Wilson loves to do.
5. and 6. Anthony Beale and Raymond Lopez
The last alderman who went directly to the mayor’s office was Monroe Heath — in 1876. Voters want a candidate who’s been responsible for more than 2 percent of the city.
7. Kam Buckner
Buckner is a second-term state representative who represents half of the fancy lakefront district Barack Obama drew for himself when preparing to run for the U.S. Senate. Stretching from the Gold Coast to South Chicago, it’s a great base for fundraising (which was Obama’s intent). However, if there’s any politician more obscure than an alderman in Chicago, it’s a state legislator. Harold Washington and both Daleys started out in the Illinois legislature, but all served in bigger offices before running for mayor. (Daley I was Cook County Clerk, Washington was a congressman, Daley II was state’s attorney.) Buckner should do likewise.
8. Stacy Davis Gates
Chicagoans supported the Chicago Teachers Union in its 2019 strike, which reduced class sizes and won teachers a 16 percent raise over five years. Does that mean they want the CTU’s political and legislative director in the mayor’s office, giving teachers whatever they want? Probably not.
9. Bill Conway
In 2020, Conway, a former assistant state’s attorney, challenged Cook County State’s Attorney Kim Foxx in the Democratic primary. Conway’s campaign was funded by his father, the billionaire co-founder of the private equity fund The Carlyle Group. Conway lost, 43 percent to 35 percent. In the city of Chicago, the margin was 55-27. Prediction: Chicagoans don’t want a rich white narc as mayor, either.
10. John Catanzara
Chicago has three neighborhoods with concentrations of Republican precincts: Mount Greenwood, Canaryville, and West Rogers Park. So Catanzara, the Fraternal Order of Police president and Trump supporter, has a base. Lightfoot was correct when she said a Catanzara candidacy would be “a gift.” He may be the only candidate on this list who couldn’t beat her in a runoff.
11. William “Dock” Walls
The former Harold Washington aide hasn’t announced he’s running for mayor again, but he belongs at the bottom of the power rankings anyway.