My last talk with Cook County Sheriff Tom Dart was in December 2011, two months after he ended his mayoral bid just when it seemed to be gaining traction. The father of five young children—a firstborn son and four daughters to follow, all neatly spaced two years apart—told me at the time that he couldn’t figure out how to be, simultaneously, the father he wanted to be and the mayor of a big, messy city.

Many viewed Dart as the one Chicago guy—a lifelong South Sider (South Shore, Beverly, now Mount Greenwood)—who could win against the force of energy that was Rahm Emanuel. Dart had hired the smart and nationally recognized political strategist Joe Trippi—he ran Howard Dean’s 2004 fight for the nomination—to manage his run. Dart’s wife, Patricia, from Central Illinois and a former policy adviser to Mike Madigan, was all in. But it was not to be, and Dart even admitted to the Tribune at the time, “I’m disappointing people.”

Six years later, with Emanuel "politically kneecapped," Dart is hinting that he’s ready to try again for the mayor’s job. His youngest is now six and his eldest 14. The latter, following in the footsteps of his father, uncles, grandfather, and great-grandfather, is a freshman at the private, Catholic, all-boys Mount Carmel in Woodlawn. Before that he attended the neighborhood school Mount Greenwood Elementary, where his four sisters now go.

Dart is Catholic—he attended Catholic schools from high school through law school, and served five terms in the state legislature before making a failed run for state treasurer against incumbent Judy Baar Topinka. In Springfield, Dart developed a reputation for integrity. He was one of the few state reps who did not hold a second job. He was first elected sheriff in 2006 and reelected in 2010 and 2014.

He has deep roots in the 19th Ward. His late father had been a Springfield lobbyist for the first Mayor Daley and his younger brother, Tim, is currently a lobbyist who represents clients before the state, city and county.

I met Dart recently for lunch at the Greek Islands, and he confirmed he’s considering changing jobs. The 53-year-old has gray curls and rimless glasses, and his style is shabby preppy—khakis and a worn Mount Carmel baseball fleece over a collared striped shirt.

He avoided the question of whether Mayor Emanuel, facing reelection, deliberately held on to the videotape of the police shooting of Laquan McDonald, but spent many minutes lovingly describing the videotape his wife made of him surprising their children on Christmas morning with a gift box containing a golden doodle puppy.

We talked for more than two hours. Here’s a condensed and edited transcript of our conversation.

Let’s start with Rahm, the guy you could end up running against. I’m sure he has heard you’re considering a run for his job. Has he given you a call?

I haven’t spoken to Rahm since the day in 2010 after I announced I wasn’t going to run. It was a very nice phone call. He joked with me that it would have been a good match, asked me if I could support him. I said I just didn’t want to get involved. I try to stay out of the endorsement world.

[Dart did not endorse in 2011 or in 2015 when Rahm faced a runoff with Chuy Garcia.]

Elections aside, one would think, given the city’s frequent shootings, that there would be a lot of reason for the sheriff and the mayor to talk.

I meet with a lot of mayors all the time; from big towns, small towns. They call me frequently to ask for help. But Rahm, no.

Are you going to run for mayor?

I don’t know. I’m interested in looking at it. Do I think I can be helpful? This isn’t an ego trip for me.

When will you decide?

In about a year.

If you decide against a mayoral run in 2019, will you run in 2018 for another term as sheriff?

I think so. I’m pretty confident that I’ll do that. The sheriff’s job will be up first, so I have the ability to run for that and then decide whether I want to run for mayor.

Have you and Joe Trippi been in touch?

No, I haven’t talked to him in the last two or three years. I’d love to work with him again. He was one of the reasons I was disappointed about not running. I’ve been around long enough to interact with a lot of people in the political world. There are good people, but there are also people, loads of them, who really stand for very little, who will support whichever candidate pays them. He was an issue-driven person who would only get involved if he thought there was someone who was trying to make a difference.

Do you think that Rahm will quit before his second term ends?

No, I don’t see that. I’ve never seen him as someone who walks away from things. But, then, it’s not as if we chat a lot.

If Rahm were to run for a third term, would you run against him in a primary?

If I decide to run, I’ll run against anyone.

Speaking about other possibilities for mayor, what’s your relationship with Toni Preckwinkle?

We have a pretty good one. We both have a lot of things we share in common; long-term changes in the criminal justice world … There will always be, no matter who’s president of the county board, an element of tension, because they’re the ones that have to tax people. People don’t like being taxed. Whereas, I don’t raise taxes, I run programs that spend money.

Do you think Preckwinkle wants to be mayor?

I honestly don’t know. We get along pretty well, as I say, but have I ever sat down with her and talked politics? No.

So you don’t have a social relationship with her, go out to dinner?

I don’t have a social relationship with anybody. I’m like clockwork. You never see me in restaurants, bars after work, and it’s not because I look down my nose at people who do that, it’s that literally the second I’m out of the office, I’m home, I’m there with my kids to read a story with them at night.

What about Rauner? Any conversations with him?

Very strange. The first month he was in office, he would give me dates [to meet] and then they got canceled. We gave him other dates. And then he never got back to us. So I’ve never spoken to him, period, ever in my life.

So how’s Rahm doing as mayor?

I think Rahm could be more inclusive, would really open up a lot more avenues to get things done. Working with people in the community. Part of the upset with him is in his style, where people feel that intellectually he’s dictating to people all the time, that he has all the answers. No one has all the answers.

Are people who work for Rahm afraid to speak their minds?

That’s part of it. I think the environment that I create is one that they don’t feel that way. “What are your thoughts?” I’ll ask. Do I have a lot of my own? I wouldn’t be doing this job if I didn’t. People in my office are engaged because I value their thoughts. I can’t tell you how many times we changed course … You sometimes get in the weeds so much that you can’t see some of the stuff around you.

Have you noticed a change in Rahm since the release of the Laquan McDonald video?

Very much so, yes, he’s much more—once again, I don’t interact with him personally—but he seems much more open, more talkative.

Do you think Rahm purposely held on to the Laquan McDonald video until after his reelection was accomplished?

Because of the stuff I’m doing I really don’t have time to stick my nose in other people’s business. I know more or less what I read in the paper.

Speaking of Laquan McDonald, a couple of your police officers were on the scene that night, arriving just after McDonald fell to the ground, and one of those officers witnessed his death. This wasn’t known until later and no police report was written. Why?

Our officers will back up other officers and other officers will back up our officers. So I have two guys on separate patrols [that night]. All the sudden they saw all these Chicago police cars flying, thought they might need backup, so they followed them. They got there after Laquan had been shot, but wasn’t dead yet. One officer saw him laying there and put gloves on and walked over to him. He told me later, “I heard Laquan sort of mumbling, kind of gurgling type of thing.” [My guy] had asked [the CPD officers] about calling an ambulance and they said they had already done that. So he just went to Laquan and knelt down next to him and said, “Just hang in their buddy; there’s an ambulance coming.” He stayed there for a few seconds and felt that Laquan had passed away at that time. My guys just got back in their cars, went back to their patrols.

The Tribune was making a big point about how there was no police report. I had to explain to them, “Look, that’s the nature of what we do. We’re always backing up Evergreen Park, Oak Lawn, Chicago. We don’t write a police report. What we have is a radio that shows they called in, following Chicago [cops], called in when they got out of their car, called in when they offered help, called in when they got back in their cars, called in when back on the road again. So there was no grand conspiracy of silence.

You regularly send back-up officers to the South and West Sides to assist CPD handling gang violence.

I’ve been doing it for five or six years now. I’m sheriff of the whole county. So if there’s one area of the county that’s particularly troubled, I should be involved with it. Chicago is one of the 120-some towns and villages in the county. When the town of Dalton had issues, the mayor called me. He gave me a building in their village to operate out of and we do. The mayors look at me as a resource to come in and help whenever they have an issue or, say, crime spiking and they need extra people. That’s not me being generous, that’s what my job is.

Were you in touch with former CPD chief Garry McCarthy and, after Rahm fired him, his successors?

When Garry first came to Chicago, he was really nice, came by my office and we talked for a couple of hours. [I told him,] “Let me know if I can be of any help.” And then I would never hear back from him, but I did hear from local commanders.

Were they happy to get your help?

Oh, yes. If you were a commander about to be held accountable, wouldn’t you like to have your area be one in which you actually have a downturn in crime as opposed to an uptick? The more bodies you put in an area, it’s an easy calculation: If you have a squad car sitting on a block, it’s likely that block is not going to have any crime. So for a local commander, it wasn’t press conference stuff. It was real bodies showing up. I would scan the numbers and see where there was a problem, and I would have one of my people call the local commander.

How many sheriff’s police do you send?

We put about 100 to 150 people in there for about a three-week period. Unfortunately, then there’s another hot spot; then we’ll move to the next one.

After he fired Garry McCarthy, Rahm appointed John Escalante as interim CPD chief. What about him?

John got ahold of me right away and we met within a week or two of his coming in. A couple of times. I’m assuming it will continue [with Eddie Johnson].

[Through his press secretary, Dart explained that he and Johnson “have not yet had time to meet due to their similarly busy schedules, [but] we’ll get them together soon.”]

Are there actual results to point to?

Yes. First, we’re taking a lot of guns off the street. Second, there’s a decrease [in shootings] while we’re there. But we would expect that. Is that sustained all the time and in all the areas? No, but we have some really interesting stats we’re looking at as far as the number of shootings while we’re in the area. And it was objectively down, but it’s a function of the fact that there’s more bodies out there.

What’s your biggest accomplishment as sheriff, and what’s your biggest regret?

My biggest accomplishment is completely transforming our eviction process from a very barbaric traditional model to a social-work model. We go to houses before evictions, work with people as far as connecting them with services, connecting them with lawyers; we help them find ways to move, where to move to.

My frustration is with how our criminal justice system as a whole deals with people who have very little voice. Traditionally those are people who are poor and/or mentally ill.

How overcrowded is the county jail?

Not at all, except in our mental health units. I put a lot of time and energy working with the judiciary to get them involved with electronic monitoring. So, instead of putting them in the jail, they can stay in their homes. When I arrived, there was probably between 10,500 to 11,000 people in the jail. Now [it’s] around 8,500.

What about that huge news story about sealing off lockers at 26th and California intended for people to store their cell phones while making court appearances?

No one ever brought to our attention that there was a problem. The initial reason they started the ban in the court is because word came from judges that people were videotaping witnesses. We got no complaints from the people who are in charge of security at the courthouse. I don’t think it was happening so pervasively that it required us to ban all the phones.

Then it got to be that there’s contraband and stuff going into these lockers and once again you would think someone would have notified us. We probably would have put cameras up. We probably would have put a sign up saying everything in these lockers is subject to search. We probably would have randomly searched.

On the good publicity side, tell me about your inmates playing chess against prisoners in Russia via Skype.

We got a Russian chess instructor, who now lives in Darien, to come in and teach chess. He has all these connections in Russia. He set up the first international chess tournament between us and Russia. The guy who has been hugely instrumental in pulling this off is [former World Chess Champion] Anatoly Karpov; somewhat like the Michael Jordan of the chess world.

Our inmates were taught in the program and some of them were real good. I think we had 18 matches and we won only two, but nonetheless we beat two Russians. They were in different locations; couple of guys in Siberia, couple of guys in Moscow, couple of guys in St. Petersburg.

We have a waiting list for [the class] all the time. If you think about it, one of the biggest things that gets people in our custody is the bad decisions; that reactive type of personality. Well, chess makes you think multiple steps ahead. So you’re left with people who never really thought that way who are now exercising a different way of thinking.

If you end up back into private life, what would you do?

This past semester, I taught. I was a fellow at David Axelrod’s Institute of Politics [at the University of Chicago]. And I loved it. I just loved it.

Can you imagine ever practicing law again?

I went to law school because I thought it would open up a lot of options for me. I never really thought about being a “lawyer.” I started after law school in the State’s Attorney’s office. I finished there in felony courtrooms, where typically you have three attorneys—first chair, second, third chair is the youngest. When I left I was in the second chair. I loved it and I was close to probably staying there my whole life, because I really had a lot of rewarding experiences helping victims of crime. But no, I don’t see myself as a law firm lawyer; I never wanted that.

And after that?

I was unemployed for a few months. [Cook County Sheriff] Mike Sheahan asked me to come and work with him, and I was his chief of staff for two and one-half years. I primarily worked on jail overcrowding issues, things like that, and then he said he wasn’t going to run and asked me if I had any interest. I thought, this is a cool thing, so I did.

When I talked to you in 2010 you told me that you had promised your son—who already had three younger sisters—that if the next baby was another girl, you would get him a male dog. Did you keep your promise?

Yes, we now have two dogs, both male, both golden doodles.

I asked you when we talked in 2010 about your experience rooming in Springfield with Rod Blagojevich. I can’t leave this go-round without revisiting the subject.

He and I had a falling out [in 2002] right after I lost the treasurer’s race. He won the governor’s race. He had asked me as his former roommate if I’d help him when he first started running, and I said sure, I could use some help too. But when it came time to help me, I got nothing, I mean literally he wouldn’t help me at all. I knew he had more money than he could spend for his campaign. I had Dick Durbin paying for me to go on state flyarounds right before election day. I couldn’t afford to pay for it and Durbin went into his own account to help me.

Did Blago deserve the 14-year sentence?

Probably excessive. I’m in the jail pretty much every day of the week and there are people in there who are convicted of murder who get 20 years. But he was deserving of significant time.

Your wife worked for Mike Madigan. Was he at your wedding?

I honestly don’t recall. President Obama [then a state senator] was there. He and I were friends. Michelle did not come. He came by himself.

Have you been to the Obama White House?

I’ve been invited, but I couldn’t make it.


When I’m not working, I’m with my kids.