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On Tuesday following Labor Day and just before the Jason Van Dyke trial gets under way, Chicago Mayor Rahm Emanuel announced he will not be running for a third term next year. “I’ve decided not to seek re-election,” Emanuel said to a packed City Hall. “This has been the job of a lifetime, but it is not a job for a lifetime.” With his wife by his side, Emanuel effectively blew open the race for the next Mayor of Chicago. To be sure, he’s had plenty of detractors from Governor-candidate Chris Kennedy to local artists like Chance The Rapper who referenced him in a recent song “I Might Need Security” with the chorus “fuck you” repeated as a backing beat. That he chose to do so just ahead of the long-awaited trial for Van Dyke, who is accused of using excessive force when he emptied 16 shots into 17-year-old Laquan McDonald back in 2014. It is widely assumed that Emanuel and his office had a hand in keeping the incident quiet for almost two years before the video was ordered released. We’ll have to wait and see how that side of things shakes out. For now though, we’ll take a quick look at some of the names initially being pushed forward to take Rahm’s position.


Paul Vallas

A former Daley-era holdout, Valles oversaw the Chicago Public Schools from 1995-2001 under the latter of the two familial mayors. He parlayed success and compliments from the likes of then-president Bill Clinton into a play for Governor in 2002 where he lost to Rod Blagojevich. Following that, he crisscrossed the country working for school districts in Louisiana and Philadelphia, amongst others while continually staying in communication with Chicago politics and flirting with several other positions. In 2014, he teamed up with Pat Quinn to run as a Democrat. They lost to now incumbent Governor Bruce Rauner and Evelyn Sanguinetti. It’s not readily clear what he’s been up to in between following a controversial situation with a potential superintendent position in Bridgeport, Conn. What is clear is that Vallas is going to have a hard time untying himself from two of the more disliked names in Illinois politics in recent memory: Daley and Quinn.

Chances: 40%

Dorothy Brown

Dorothy Brown has long been seen as one of the early names to crop up in defiance of a continued Emanuel reign. The current Clerk of the Circuit Court of Cook County, Brown has participated in races over the year for City Treasurer (1999), Mayor (2007) and President of the Cook County Board of Commissioners (2010). She has held her current position since 2000, but not without some headline-grabbing situations that have put her trust in question in a city long-known for kickbacks and greased palms. She came under fire in January 2010 for money accrued via a “Jeans Day” where Clerk’s office employees could donate cash to the Jeans Day fund and wear casual clothing to work on a Friday. An investigation found misappropriation of funds, but no guilty verdict. She was also tied to corruption charges against potential New Orleans Mayor Ray Nagin a few years back and a 2011 allegation of a building given to her husband on the southwest side. In all honesty, Dorothy Brown may have the background for this, but the more you dig into it the more it feels increasingly familiar.

Chances: 20%

Photo by @rrhinton

Garry McCarthy

If you want our honest opinion about McCarthy’s campaign, feel free to reference a previous op/ed on the subject. Still one of the most controversial declarations amongst the packed field of candidates, McCarthy is looking to return to public service in Chicago after being dispatched from his position as Superintendent of Police by Emanuel following the McDonald fallout. Having been fingered as the scapegoat for that incident which brought a Justice Department investigation, it’ll be hard for McCarthy to get the support of anyone but the most ardent police supporters and even then, he wasn’t the most popular for his practices.

Chances: 15%

Chris Kennedy

During his campaign to represent the Democrats against Rauner for a chance to lead Springfield, Kennedy made a big play against Emanuel, charging him with not doing enough for the city’s less popular corners in what he called “strategic gentrification”. While he may have bowed to the deep pockets of JB Pritzker, there have been grumblings that he may throw his hat in the ring for Mayor. While his politics would play well and his earlier attacks on Emanuel’s handling of the city’s image and finances have already seen his name come up earlier this year, his address in north suburban Kenilworth may end up keeping him on the sidelines for this one.

Chances: 20%

Willie Wilson

Willie Wilson is a name Chicago voters are readily familiar with. Having ran several times in the last two decades for mayor, he’s got the name recognition. Last month he came under fire for handing out cash to potential voters at a church on the south side. In all honesty, politicians have been giving money to those in City Hall and with varying degrees of clout in the Chicago for generations so Wilson giving it to people who can actually use a few extra dollars and being transparent about in the process may have been the most unveiled use of the local political machine we’ve seen to date. Of the candidates, the owner of several McDonald’s restaurant franchises and owner of Omar Medical Supplies, which imports and distributes latex gloves and other medical and safety supplies and equipment, seems to be the most in touch with those on the ground floor. We’ll see if he can utilize the grassroots campaign he’s had in almost constant motion since his 2015 bid and subsequent outside shot for President in 2016. So far, he’s an underdog favorite to some.

Chances: 35%

Lori Lightfoot

Lori Lightfoot is a name that has been around the city for awhile now. A career trial attorney, investigator and risk manager has seen Chicago from all angles in her time and is looking to parlay her knowledge and know-how into a successful bid for mayor. A graduate of the University of Chicago Law School, she served as Chief Administrator at the precursor to the Independent Police Review Authority (IPRA). While there, she managed a 100-person office of civilian investigators who investigated police-involved shootings, excessive force and misconduct allegations, among other duties. Her insight here may endear her to a community reeling from a wave of shootings involving officers and citizens. She also has a proven track record of standing up to established names, having investigated Tony Rezko, the former fundraiser for Gov. Rod Blagojevich, Elzie Higginbottom, the black community fundraiser for Mayor Daley, and F.H. Paschen, the head of one of Chicago’s biggest construction companies. Emanuel tapped her to head of the nine-member Chicago Police Board, which decides disciplinary actions involving allegations of serious misconduct made against CPD. In December 2015, in the fallout over the Laquan McDonald case, Lightfoot was tapped as one of six members of the Mayor’s Police Accountability Task Force. As an openly gay black woman as well, she offers a perspective that recent mayors certainly have lacked. Her background may well be just what the city needs right now if she can prove she can handle the larger context of the office.

Chances: 35%

Ja’Mal Green

A local activist and one of the younger names on the list, Ja’Mal Green represents an important side of the field of candidates. At a time when someone like Donald Trump can enter politics as a “outlier” why can’t it happen on the Democrat side of things? Green, like Chuy in the last election, represents Chicagoans best opportunity to be represented by someone with their own perspective. Whereas other candidates announced so far are career politicians, Green appears to advocate for the causes he actually believes in, and isn’t afraid to protest or get arrested to prove his point. He started his first youth organization at 15 and has been dedicated to fighting for the injustices he experiences firsthand growing up on the city’s south side. At only 23, Green is definitely the outlier on age and experience, but given the amount of corruption and disarray that older folks have been causing in this city for generations, maybe a young independent voice is exactly what we need.

Chances: 35%

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