There are only a handful of FIBs that we love, and Charlie Connelly is one of them. The current Manager of Corporate Partnerships for the Milwaukee Admirals, Charlie has helped to elevate the minor league team, drawing new fans and partners to the Admirals.
But his life outside of work is equally as important as the passion he has for the Admirals. Charlie enjoys helping young athletes unlock their potential: he serves on the board for Girls on the Run and is Dominican High School’s assistant baseball coach. He’s also his wife’s number one fan.
We talked with Charlie to learn more about his path to the Admirals (hint: cut throat advertising industry), his ties to the community, why he made the move to Milwaukee, and what he hopes to see for the future of the city he calls home.
What is your background?
I am from a smaller town in the Western Suburbs of Chicago. Riverside, Illinois. I won’t lie and say “I’m from Chicago”. I usually shorten the answer to “the Chicagoland area” to avoid offending true Chicagoans. I grew up in Riverside, moved to Lakeview in Chicago when I was 19, and then moved to Milwaukee when I was 21. I’ve been in Milwaukee ever since and have loved every minute of it.
Any stories from your youth that define your path?
There are several stories, and certainly influences, from my younger days that have shaped me. I am one of five siblings and a product of a divorced family, which has given me two gifts – a strong support system and a sense of humor.
One childhood story that stands out in particular comes from my summer going into freshman year of high school. My twin brother, a group of friends, and myself were given 20 hours of community service for trespassing on our school’s roof. For our community service, a few of us chose to volunteer at the local retirement community. What was originally 20 hours of court mandated community service turned into over 225 hours of volunteer work at this retirement community over the course of my high school career. I really grew an admiration for the residents, their stories, and the time I spent there. That would have never happened if I hadn’t made that initial mistake.
One learns a lot more from their mistakes than they ever do their successes. Whenever I speak to school groups or people early in their career looking to get their start, I try to remind them that. I’ve actually never shared this specific story in a professional setting though, so Milwaukee Uncut gets this uncut scoop on 14-year-old Charlie Connelly breaking the law.
Where did you study (if you did higher education)?
Columbia College in Chicago. I’ve also learned that if I just tell people Columbia, it’s not worth correcting their assumption. Columbia College is a great Art school, but what a lot of people don’t realize is its Journalism and Advertising programs are arguably equally impressive. I loved my time at Columbia. As a sophomore, I became the Advertising & Business Manager for our school newspaper, and that’s when it became clear I could find a pretty exciting career in media sales.
What do you do for work now?
I am currently the Manager of Corporate Partnerships for the Milwaukee Admirals. I handle sourcing new partners of the Admirals and executing some pretty exciting work in-game and in our community. I know that people can get confused by the term partnership. Is that just a paid sponsorship? It can be if you view it that way.
With every partnership our team executes, I really do make it my primary goal to not only deliver on what the contract outlines, but also ensure it’s really a two-way relationship. What can I really do to help advance their company’s mission? What can the Admirals gain in that process as well?
I enjoy my job because I remember what it was like to go to White Sox games growing up and seeing the entertainment experience blow me away. The fact that I can have a small hand in delivering a similar sense of wonder to young kids here in Milwaukee is special.
Can you talk a little bit about your career journey? How’d you get to where you are now?
I am in media sales and have been for a decade now. Time flies. It all started though when I found out I was actually decent at the job. I switched my major from Journalism to Advertising and saw that my college newspaper was hiring in the Advertising department. I interviewed and landed the Advertising and Business Manager position right away.
What I didn’t realize at first was that was by necessity and the upper classmen in the Advertising department had graduated. I cut my teeth on digging up old account records and making phone calls. In a short period of time, I was managing a book of clients who paid roughly $30k a week to advertise in our newspaper. At 18, I learned quickly how to build trust and strong relationships in the business world.
I’ll never forget the advice that the VP of Sales at the Chicago Tribune told me when I went with a group of college newspaper ad managers to shadow his sales floor for an afternoon. He told us that we do the exact same thing that he does, he just happens to do it with more zeroes at the end of each contract. That line really stood out to me, and still does.
I had three valuable internships during my college career, and then landed my first full-time position in media sales for a trade publication in Chicago. My world was opened up quickly in that role. It was a churn and burn environment and ultimately wasn’t for me. After a brief stint there and then a year in the sales department at Interpark, I was hired at the USA TODAY Network, which owns the Milwaukee Journal Sentinel here in Wisconsin. I grew from a local territory rep to a senior key accounts rep in just over four years, and was managing the largest panel of business in the Midwest by the time I left for the Admirals.
Now being in the entertainment and sports business, I’m reminded how there’s no one direct path. That’s the beauty of it.
Can you talk more about your community involvement?
I currently serve on the Young Professionals Board for Girls on the Run Southeast Wisconsin and am an assistant varsity baseball coach at Dominican High School in Whitefish Bay. I’m passionate about athletics, but really not from the physical side at all. I’m most interested in helping young people unlock whatever it is their unique potential is. Kids often find what that potential is through sports, and it ends up having nothing to do with the physical side of the sport at all. Sports teach us all about sacrifice, commitment, dedication, failure, and the list goes on. In my work with Girls on the Run and Dominican baseball, it’s all about helping kids discover those life lessons for themselves.
What are some ways you have impacted the community in your line of work?
In my role with the Admirals, I’m fortunate to play a small role in impacting the community on a regular basis. Specifically, I enjoy the work we do to support Children’s Wisconsin. Every year, we host an annual game for charity where $3 from every ticket supports the amazing work being accomplished at Children’s Wisconsin. Along with that, I get to help play quarterback on executing the partnership with our annual player visit, where we have Admirals players come into the hospital and play games with patients. I’m now in the midst of planning a blood drive at our arena with Versiti Blood Center of Wisconsin in January 2026. There’s always something we as an organization are touching that helps give back to the community that supports us so much. That’s how I view it. It’s really a two-way street.
What do you like about living in Milwaukee?
I really like the people here in Milwaukee. Milwaukeeans don’t take themselves too seriously, but sometimes maybe not as serious as they should. I also really enjoy that you can get anywhere in 15-20 minutes. Milwaukee is like Chicago, without the BS.
What do you want to see for Milwaukee’s future?
I want to see Milwaukee continue to evolve, in it’s own unique way. I love that Milwaukee is what it is, and doesn’t necessarily try to be what it’s not. We don’t need another Chicago on Lake Michigan.
Anything else we should know about you, your job, community involvement, or life in general?
I am a very proud husband. My wife Katie does an incredible job serving our community as a high school Athletic Trainer and making sure our lives are running in the right direction. I have a front row seat every single night, hearing about her athletes’ needs and the care that she provides them. I couldn’t be more proud of her. While I am proud of my career, it really means nothing compared to the life we’re growing together. That’s what I’m most proud of.