04/27/2026
Meet Paul Winberg, MPA '98, CEO of the Grant Park Music Festival, Chicago
For more than 14 years, Paul Winberg, MPA, helped grow and sustain the Grant Park Music Festival’s artistic excellence, financial strength, and public impact.
The following is an edited transcript of our interview with Paul Winberg.
CUPPA: How did you make your way to the UIC Master of Public Administration Program?
PW: This comes up a lot in conversations I have with people; they often ask me why you did your MPA and not an MBA. And then I have to reflect, ‘Oh, why did I do that?’ If you just rewind the clock a bit, when I graduated with my undergraduate degree, I was at the University of Michigan at the music school there. I studied music and theater and came to Chicago to be a performer. I was a gigging performer and at the time, I had the opportunity to take an entry level full-time job for a start-up non-profit organization that popped up to try to address the HIV crisis that was happening in the Chicago area at the time.
That work led me into the nonprofit world. Battling HIV led to another job, and another job, and then I worked for the AIDS Foundation of Chicago, and then I was working for a company that was connected to Saint Joseph Hospital that was doing clinical drug trials. I worked my way up into being their financial business manager, and I thought, I love the work! I mean, it was important work and I felt good about that. But I also missed the performing arts side of my portfolio.
I began to think about, well, if this is where things are heading for me, I really need to find a way to transition out of healthcare and use the skills I had acquired and try to align them into the performing arts. That’s really what propelled me into going back to school. I was looking at a variety of different programs. The reason why I felt I needed to go back to school is because I was coming out of an undergraduate program in music that was very vocational in many ways, like we had to take liberal arts courses, but everything was very much geared to being a performer. So, I didn’t have the opportunity to take a statistics class or to take economics, some of the things that I really felt were important skills in order to succeed as someone who ultimately wanted to lead a non-profit performing arts organization.
I was really looking across the landscape. I was living in Chicago. I didn’t have much money, you know, I was working in a nonprofit. I was looking at a variety of graduate programs and the MPA program kind of popped into my radar and it seemed like it would make more sense if I’m pursuing this non-profit world rather than an MBA. At the time University of Illinois Chicago was the only school in Chicago offering an MPA program that was fully accredited. There was one at Northern Illinois University and I think there was one in Champaign, but I wasn’t leaving Chicago.
CUPPA: Can you tell me more about your time in the program?
PW: When I enrolled in the MPA program, it was very much a generalist degree. It did not have a nonprofit emphasis. I really liked the idea of a generalist degree. Each time I had to do a special project throughout my MPA, I just focused it on non-profit enterprises. I was able to tailor the program to exactly what I was aspiring to do once I finished the program.
I found the program to be very rigorous. I really enjoyed the faculty. I remember when I first started the program, I was so intimidated by everybody. Especially in the larger cohort based classes. I remember when professors would call on me to say something and I’d just be so anxious about it. Then I remember in my final year being in smaller classes, where we’d have very intense discussions about readings, and you couldn’t shut me up. That was a huge transformation for me, going from being completely intimidated by everybody around me to really feeling confident about what I learned.
I was also able to apply some of the things I Iearned in my work life before I entered the MPA program, and that was helpful for understanding the context of the work that we were doing and the topics we were discussing. My prior experiences were also helpful in discussions with other students.
I took statistics class, and economic class and administrative law. Those classes were completely eye-opening and helped me understand the universe in a way that I didn’t appreciate before. It also really opened my eyes about the interconnectedness and the organic nature of how we’re all working in this collective ecosystem. I would have never thought about the world that way had I not participated in a program like the MPA program. I might not remember exactly how to run a regression, but I do remember what it taught me.
It's an outstanding program and on top of that it was the most affordable program. I can’t stop singing the praises of the program when people ask me about how the program was structured, the faculty, and how much I took away from the experience. It really was transformative and set me up for success.
CUPPA: You came into the program with such a clear focus and things have really played out exactly how you planned them in a way. Has there been any deviation in your career path since that time?
PW: I didn’t realize how hard it would be to break into the administrative side of performing arts. I felt so credentialed and ready to take on the world and the barrier was, you really have to start in an entry level role. My internship was actually with the Grant Park Music Festival back in 1997. It was a really intense experience, but as an older student with a bit more perspective and experience, I really just tore into it and I just said yes to everything, probably overextended myself during the time, but I had just wanted to learn as much as I possible could within the internship timeframe.
That internship propelled me into my first position, learning how the production side of creating orchestral concerts, then I worked in development. Throughout all of my experiences, I stayed focused on my becoming an executive director along the way. There were many different places where I could have either parked myself or stayed. I could have stayed in development or marketing, but my background and experience, and I think the MPA degree in and of itself, kept positioning me in a favorable way so that people were really asking me to step into different roles. I was given these unique and interesting opportunities to kind of continue this upward trajectory.
Once I felt like I had a really good grasp of our foundation, and had experience in many of the administrative departments, I felt very confident taking my first executive director role.
CUPPA: Is there any advice you would give to MPA students that are soon to graduate?
PW: When you’re coming off a degree like the MPA program, it’s important that you don’t need to start right at the top. It’s important to learn as much as you possible can by taking on these different roles so that when you do get the top position, you are really equipped to truly understand the scope of the organization and also be a real resource to the staff that are reporting to you, and be a true thought partner with the people that are reporting to you. I oftentimes tell younger folks who are way more ambitious than I was at that age that it’s OK to take your time and there will be rewarded for doing that.
CUPPA: I know you have been instrumental in getting municipal funding for Grant Park Music Festival. One of the Professors at CUPPA often says work moves at the speed of trust. Can you tell me more about that work?
PW: Grant Park Music Festival works very closely with two huge bureaucratic municipalities. One is the City of Chicago and the other is the Chicago Park District. They are two separate organizations with their own taxing authority. Had I not had my MPA, I never would have understood the difference between one another.
In terms of working at the speed of trust, one of the biggest challenges for me in my relationships with both the city and the park district is that once you are able to establish trust with say the Commissioner of the Department of Cultural Affairs, who I interact with, or the Superintendent of the Chicago Park District. We build really great rapport with one another, which is so important to the festival in terms of maintaining support and funding. Then a new mayor comes and the entire administration shifts and I’m starting all over.
It’s very true that you can’t get anything done if you haven’t worked to build those relationships and build that trust. So much of it relies on the relationships that you identify, build and nurture in order to get things done. It’s an ongoing part of the work that I do and in a way that I never really expected it would be. I think one of the reasons why I have been successful in navigating it is that I understand it because I studied it. I understand that budgeting is a political process. Making decisions about resource allocation is completely a political process and I have to be part of that process. So tying it back to the MPA program, what I learned from my graduate work has been helpful in navigating that process.
CUPPA: It was announced that you’ll be retiring from the festival. What’s next for you?
PW: I’m not sure what it will look like, though I’m going to take the summer to kind of think more about that and then recalibrate. In the meantime, I have been studying piano again. I have found that going back to where it all started, as a pianist and performer, has been a great outlet for me.
CUPPA: Thank you, Paul and best wishes on your retirement and adventures to come!
