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Matt Hynes, the director of intergovernmental affairs for the Emanuel administration, is leaving after three years on the job. | Richard A. Chapman/Sun-Times

Matt Hynes on lessons learned on front lines with Mayor Emanuel

He used lessons learned from his political pedigree to help Mayor Rahm Emanuel start down the road to pension reform, build surprisingly strong ties to labor leaders who opposed the mayor and deliver a $375 million plan to renovate Wrigley Field that has yet to turn a shovel.

Now, he’s leaving the grueling hours behind to reconnect with his young family and resume his legal career while steering clear of lobbying.

Matt Hynes — the 43-year-old son of former longtime Cook County Assessor Tom Hynes and brother of former state Comptroller Dan Hynes — is stepping down as Emanuel’s $168,996-a-year director of intergovernmental affairs as Emanuel hunkers down for what could be a difficult re-election campaign.



Hynes was Emanuel’s chief liaison to organized labor, the City Council and Springfield. His departure leaves a giant void as the mayor seeks to nail down a police contract, pension deals with police officers and firefighters, and crucial votes in the City Council and Illinois General Assembly to pay for it all.

He’s also part of a powerful triumvirate of City Hall decision makers that includes Chief of Staff Lisa Schrader and senior adviser David Spielfogel. 

“Matt’s title of Senior Advisor doesn’t fully capture all of his contributions and commitment to the City of Chicago and my administration. He has been on call 24-7 for the last four years and the City and I will forever be grateful for all of his efforts,” Emanuel said in an emailed statement. “Matt has been my trusted advisor and confidant since the days on the campaign and though he may be leaving City Hall, he will continue to be someone whose counsel I rely on.”On Tuesday, Hynes sat down with the Chicago Sun-Times to reflect on his hard-charging boss and the three years he has spent at the center of power. Here is an edited version of the interview. 

Q: What did you learn from your father that helped you do this job?

A: I learned a lot about how to treat people and listen to what they have to say. If you can’t use what they suggest, let them understand why you’re doing something differently. He had a very good style that I’ve always tried to incorporate. To do this job, you don’t always have to be a jerk. You don’t have to be a tyrant. You can be professional and work with people in a way that makes people want to work with you. You get better results that way.

Q: That’s a style that’s a lot different from Rahm Emanuel’s cartoon image anyway.

A: Yeah, but his style is so collaborative. People do not give him credit for how he really is. He’s very accessible, open to other ideas. He always wants to get people to a mutual agreement. That’s why it’s fun to work for him. It makes my job a lot easier.

Q: Where are you going?

A: I’m not gonna be talking about it until things are final. What I’m gonna be doing in the short-term is spending a lot of time with my family . . . And, as a volunteer, I’m gonna spend a little bit of time on the mayor’s campaign effort to get it off the ground.

Q: What’s it been like to work for this mayor? We had a police superintendent who had a heart attack. He was so driven by the pressures of the job.

A: It’s been incredibly rewarding. Yes, he is a demanding boss. We’re taking on a lot, and he expects a lot from his staff. But it’s actually a great feeling to be part of that. Not something where you feel like you’re driven into the ground. We all work very hard. But it’s kind of easy to do when you see how hard he works. So you don’t feel sorry for yourself.

Q: You’ve spent hundreds of hours on Wrigley Field and you haven’t delivered that yet. What happened?

A: We made a lot of progress. But there are certain things outside of our control. What we did is put in front of all the parties the groundwork in order to get to a yes, which is still possible. The mayor delivered on all of the things he said he was going to do. The rest is up to the other parties to step forward and get to a point where we can put this behind us and start investing in the community.

Q: How frustrated are you with Cubs Chairman Tom Ricketts and the fact that, with all you’ve done to deliver, he kept you in the dark about enlarging the bullpen doors and altering Wrigley’s ivy-covered brick walls?

A: That was a minor setback, but one that can be overcome. I don’t think it was an intentional effort on the Cubs part to sneak the goods through customs. But once it came to the mayor’s attention, he made his opinion pretty clear. But you’ve got to look at the big picture. It’s important to have the Cub investment in the park and in the community go forward. So you move past it. There’s not a whole lot to be gained from harboring bitterness when you’re trying to get a deal done.

Q: How did you feel about Ricketts cutting off negotiations with the rooftops and returning to his original plan for seven outfield signs?

A: The Cubs perspective is, if we’re gonna be going to court, let’s make it all or nothing. There is a certain amount of logic to that point of view. They own Wrigley Field. While there are restrictions, they have right to at least seek the ability to do what they want with their park. It’s not for the mayor and certainly not for me to tell them they don’t have that right. . .  But there is a process. They know that and they have to go through it.

Q: You also spent countless hours negotiating pension deals with the Municipal Employees and Laborers Unions. How tough was that?

A: Everyone understood how big it is. That causes sleepless nights. That causes a certain amount of anxiety because it’s huge. And it has an impact on people. That’s why these things take so long.

Q: But police, fire and teachers remain.

A: One thing that is good with regard to pension reform is that there’s definitely momentum in the state for it. We’re on the verge of being done with it. There’s some big pieces still to solve. But there have been a series of bills passed and signed by the governor. That’s a good thing. Something to build on. It’s getting to the point where people can see the light at the end of tunnel.

Q: Gov. Quinn has asked the mayor to rule out a property tax increase. Can that be done?

A: The income tax question still has not been resolved on the state level. There are a lot of things out there we don’t know yet. There may be opportunities for the state to provide assistance.

Q: But where is the money going to come from to meet your obligations to Municipal and Laborers and do the same for police and fire, whose reforms will not be as lucrative because of the nature of those contracts?

A: There are new ideas that can emerge at any time that could provide significant revenue to the city…And you have a statewide issue, which provides opportunity.

Q: Could there be a sales tax on services that becomes a statewide solution to the statewide problem of police and fire pensions?

A: A lot of elected leaders in Springfield want to have a sales tax conversation. But I don’t expect anything to occur on that until certainly post-election.

Q: Your own brother proposed that during his 2010 gubernatorial campaign. The mayor also talked about it. They called it the “Rahm tax.” It makes sense, doesn’t it?

A: Part of what you want to do when you look at the sales tax is also provide relief to people in terms of the current sales tax structure.

Q: You dealt with Fraternal Order of Police President Mike Shields. Now, he’s out of there and been replaced by a much more moderate FOP president. Is the city making any progress with police in contract talks?

A: There’s been an opportunity to hit the reset button with the new leadership. The mayor has had productive conversations. I expect over the summer, there will be serious conversations on collective bargaining. There’s reason to believe this will be a productive process.

Q: What was it like being a top mayoral aide during Chicago’s first teachers strike in 25 years? Was that the low point?

A: It was intense. Surreal at times. You have a very large event occurring and you’re in the middle of it. . . .  The weeks leading up to it were, in some ways, a little bit more intense than after it had actually occurred. You obviously don’t want it to happen. Once it occurred, your mind-set changes and you’re more in the moment dealing with it. There were a lot of logistics. You kind of go into auto-drive once it occurs. It was a moment in history.

Q: Could it have been avoided? Was it provoked?

A: I don’t think it was provoked. . . .  The mayor was fighting for the right issues. . . .  He was led by the right principles and made the right decisions. No one is glad there was a strike. You always look back and see if you learn from things.

Q: But the mayor still doesn’t have a dialogue with Chicago Teachers Union President Karen Lewis. Why not?

A: I don’t know. . .  The mayor has shown that he is always willing to continue to look to the future.

Q: School closings have hurt the mayor, particularly in the black community. There’s a disconnect when you’re closing schools, but opening charters and building schools on the North Side.

A: The mayor is very committed to trying to build up the school system in the right way. A lot of these decisions that have been put off are very difficult. No question about it. It’s not that he relishes these things. But he knows that tough decisions have to be made. It certainly isn’t easy on the people impacted. But he’s trying to do what he thinks is right.

Q: Did he do it in the right way?

A: Time will tell that. Transforming a school district is not something you see the next day. You see the signs of positive results and you try to fan those things and make them grow into something bigger.

Q: How would you characterize the mayor’s relationship with labor leaders, many of whom opposed his candidacy?

A: Very strong. Once various leaders in labor got an opportunity to work with him and got to see what his values and principles were, some of the myth of what maybe his experiences were in Washington completely evaporated. He’s got very strong relationships. We’ve made incredible deals. Our collective bargaining has gone really well. They’re on the same page in terms of investing in our infrastructure and in our convention and tourism industry. He has knocked down some of the ideas that may have existed when he came into office.

Q: How much trouble do you think the mayor is in as he stands for re-election. Our Sun-Times poll shows 29 percent support.

A: The mayor is gonna be tough to beat no matter who runs. He’s in a very strong position. When you look at the accomplishments across the board and you’re able to put that into context for the voters, it becomes very clear that he’s actually been taking on tough challenges and getting results. . . .  He’s an authentic person. He is strong. He does care. And he is willing to fight fights that have been put off in order to get results. That is why he was elected. That’s what he’s doing. That’s why voters are gonna want to see him stay in office because they know that we still have real problems yet to deal with.