Politics – it is a double-edged sword in Chicago. For some, it never stops, while for others too much time is spent on it. Here we are about two years away from the next race for mayor, and the discussions about who are the best candidates are already heating up. Never mind many of us are leap-frogging next year’s gubernatorial election to talk about unseating Mayor Emanuel. Yep, there is nothing like Chicago politics. 

It’s a certainty that if the rumored and hoped-for candidates jump into the mayoral fray, Chicagoans will have the best line-up of bonafide candidates in decades. Of course, there will be an outlier who enters because of ego or the need for name recognition. That just goes with the territory.

There are a few variables but it looks like the lineup will include some political veterans along with a couple of newcomers.

Tom Dart

Amara Enyia

Jesus (Chuy) Garcia





Troy Laraviere

Kurt Summers




Tom Dart without question brings the most robust governmental resume of anyone thinking of running. He’s been:

  • a state prosecutor
  • a state senator
  • a state representative
  • a sheriff department chief of staff and,
  • currently, the Cook County Sherrif  

    Sheriff Tom Dart

That equates to a wealth of campaign experience, and simultaneously the opportunity to create a lot of goodwill as well as have some develop hard feelings toward him.

Mr. Dart has proven to be innovative as he has churned out initiative after initiative to reduce jail overcrowding, as well as work with others to develop favorable bond options for minor misdemeanors. His political appeal is felt on the South Side, North Side and West Side Raising money should not be a problem for him, and campaigning will be second nature. That level of appeal will be a major factor in Mr. Dart’s favor should he decide to run. It means it is one less obstacle he will have regarding votes along racial lines

Amara Enyia, no doubt took away a lot of lessons from a campaign that had an extremely difficult time getting out to of the starting blocks when she decided to challenge Emanuel in 2015. She is as equally versed in public policy as any other prospective candidate, and better than the rest. Besides her endless knowledge of budgets and governmental operations, Ms. Enyia did what some many unsuccessful candidates for public office don’t do – she remained highly visible after the election. That move spoke volumes about wanting to occupy the big chair on the fifth floor.

Amara Enyia

Not only has she embarked on speaking engagements across the city, she has made certain she has not been put in Black candidate box. She seems to belong to the people. Look for her to be an Obama-esque fundraiser, and that is amassing a war chest from a very expansive base of small amount donors.  She is likely too to be the only candidate who not only appeals to millennials but can get them to the polls. 

Voters on all sides probably still remember that two years ago Cook County Commissioner Jesus “Chuy” Garcia forced incumbent Mayor Rahm Emanuel into a runoff election. While he showed a depth of knowledge consummate with his county experience, and time as an alderman; Mr. Garcia was a tepid campaigner, He often failed to show the passion many voters wanted, nor was he quick to counter many of the mayor’s jabs.

Cook County Commissioner Jesus (Chuy) Garcia

His campaign also was crippled by a Black undercurrent promoting the idea Black people will be shut out of government in favor of those of Mexican ancestry, as Mr. Garcia is Mexican. Some of his current backers say we should expect to see a forceful Chuy if he gets back into the fray.

The long-shot among potential candidates is Troy Lariviere.The young former CPS principal made a name for himself by openly and repeatedly challenging Mr. Emanuel’s policies on education – particularly school closings and resource allocation.  

Troy Lariviere

HIs position resonated with residents, and as is the case politically in Chicago; when someone is anti-incumbent there is a cohort pushing that person as a viable opponent. Hopefully, Mr. Lariviere.see that a city council see will afford him the background and knowledge needed to make a solid mayoral bid down the road, 

Chicago City Treasurer is the x-factor on the who will be next mayor list. Mr. Summers is widely rumored to edging toward a run against incumbent Gov. Bruce. That race would be a better fit because even though it is state-wide, it would be less grueling than a Chicago mayoral election. Mr. Summers’ portfolio doesn’t include much retail politics campaign experience.  There is plenty of city hall observers who like his chances of running for mayor.

City of Chicago Treasurer Kurt Summers

The problem there is it would make for a mighty uncomfortable tenure as treasurer, given Mr. Summers would be running against his boss, the man responsible for him having the job. There is no denying Mr. Summers is among, if not the brightest star in the Democratic Party sky.

An upside to election talk this far ahead of the vote is citizens might be nudged to start paying close attention sooner to what potential candidates are saying and doing. Voters should begin to study the problems with the budget to be able to ask the tough questions that are too often avoided.Using these two years to gain a better understanding of how the city council operates is another area that deserves attention,