Cook County Sheriff Tom Dart
Tom Dart
Soon after Rich Daley announced in September that he would not seek another term, Cook County Sheriff Tom Dart jumped in the mayor’s race. Though he never officially announced, Dart withdrew in late October, saying he couldn’t be mayor and a good father to his five children at the same time.

He had a good shot at winning, even with Rahm Emanuel strutting back into town. With ties deep in the 19th Ward—his late father was the first Mayor Daley’s main lobbyist in Springfield—the 47-year-old Dart seemed the golden boy to beat. He had taken a county office and turned himself into a national star, refusing, for starters, to evict tenants who had paid rent to landlords who then defaulted on their properties. Last year, Time named him one of the world’s 100 most influential people. Since turning his attention back to the sheriff’s office, Dart, who was easily re-elected to a second term last month, has continued to accumulate accolades—most recently when the Chicago Tribune called him a “hero” for pushing his 7,000-employee department into compliance with the Shakman decrees that limit hiring and firing government workers based on political loyalty.  

What’s next for Dart, a lawyer, who talks about sticking to the sheriff’s job “definitely” for the next four years? And whom, if anyone, will he endorse for mayor? Here, some answers from our hour-long conversation:

CF: Any regrets about leaving the Mayor’s race?
TD: I honestly find myself saying to myself, “What in God’s name was I thinking?” My two older daughters particularly were crying a lot, and when I tried to leave the house they’d hang on to the door handle. I’d have to almost try to tear them away, and then it got to the point where my wife would have to keep them at the front door while I’d run out the back door and they’d come crying after me.

CF: You have five children ages one to nine, one born every other year. More to come? 
My nine-year-old is a boy and then it’s four girls. When number five was imminent, we struck a deal that if my son and I did not get another boy that we were going to get a male dog. We do not have the dog yet. I think it’s going to be another year or two before we wear my wife down, with enough whining from both of us.

CF: Rahm is taking a beating for not committing to send his kids to public schools. Do your children go to public school?  [The Darts live in Mount Greenwood on the Southwest side.] Is it fair to ask that question of a candidate for mayor?
TD: Yes, the three who are school-age are all in public schools. If somebody says, “Yes, I feel very strongly about the public school system; however, in the area we live, the school has always been ranked below average and as a result of that I want to send my child to a place where they get a better [education],” it’s a well-thought-out answer [and] people should be able to send their children wherever they want to send them. But it is a little bit tricky to have someone going on and on about the merits of public education, and they have a good school but don’t send their child there. 

CF: You say that Emanuel and Gery Chico and most of the other candidates have “reached out” to you. Whom will you endorse?
I don’t think I’ll endorse anybody. I’ve told them after the holidays, “If you want to talk with me, I’ll talk with you, but the chances of me endorsing anybody are horrifically slim.”

CF: I’ve heard that you were having trouble raising money and that’s why you bowed out.
TD: I was shocked at how easily the money was coming in. We had raised a ton and I was being very, very well received by the business community, the liberal community, a lot of Republicans. The money was coming in embarrassingly quickly, and that was without a dime from the unions who made numerous representations that there would be a lot of money [coming from them].

CF: What do you think about Rahm and the residency issue?
I had a lot of people coming to me, [encouraging me to challenge Emanuel on the issue]. I didn’t seek them out. I never hired a lawyer, never got involved in the whole discussion—God is my witness. But I had a lot of lawyers coming to me because I think they were thinking I’m the frontrunner, so this is a good thing for you to get involved with. A lot of them were very clearly saying that [the residency challenge] is a serious issue.

CF: You spent the longest part of your career [1992 to 2003] as a state rep. Why did you leave?
I was one of the only lawyers down there who didn’t practice law, and my entire life and salary was my job in the legislature. Then they changed the rules of the game. My first three to five years, I was introducing a hundred some bills a year. Then it became like Washington; it was leadership-heavy where every bill, every amendment, had to go through a rules committee run by leadership, and they would only allow three bills a year to be heard.

CF: When you say “leadership” you mean Speaker Mike Madigan? 
Oh, God, yes. He and I butted heads a lot.

CF: Had you stayed in the mayor’s race, would you have sought his endorsement?
I called him a few weeks after I had sort of thrown my hat out there. He said we’d talk down the road once things started shaking out.

CF: You served in Springfield with Rod Blagojevich. Were you buddies?
TD: We roomed together for a year—lived in a two-bedroom apartment. He had one or two bills he really put some energy into. We’d be on similar committees and I’d be heading off to the committee and he’d be heading off to run. He’d say, “None of that matters, no one cares, not a big deal, screw that, wasting time.”

CF: Did he spend a lot of time on his hair?
He’d get pissed when I’d mess it up, tousle it as he was going out the door to run. I’d say, “You have to go comb your hair again.”

CF: Do you see yourself running for mayor down the road?
There are a handful of offices that I would consider at some point in my life, and they would be executive offices where I can get things done pretty quickly—such as governor or mayor. I view my life as a very short life, a very short period of time I’m on this earth. I want to get stuff done while I’m here. [As sheriff], if I wake up one morning and say, “The eviction process is unjust,” I don’t have to introduce a bill, I don’t have to run it by leadership, I don’t have to get 60 votes. I can just say, “You know what, guys? We’re not doing evictions anymore.”


Photograph: Chicago Tribune photo by Terrence Antonio James