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Milwaukeean of the Week

From Transplant to Match of the Year: How an Illinois Native Found Her Purpose in Milwaukee

When Gabbi moved from Naperville, Illinois to Milwaukee in 2019 to join Teach for America, she couldn’t have imagined that her journey would lead to being named the 2025 Match of the Year by Big Brothers Big Sisters of Metro Milwaukee. Her story demonstrates the transformative power of meaningful relationships, both as someone who received crucial support during difficult times and as someone who now provides that same support to others.

Gabbi’s path to mentorship was deeply influenced by her challenging high school experience. Struggling with significant attendance issues and uncertain whether she would graduate, she found her footing in supportive teachers who saw her potential. “One of my main motivators in high school was the close relationships I had with multiple teachers,” she recalls, giving special shoutouts to Mr. B. and Ms. T. “They truly helped guide me through life both in and outside of the classroom.”

These relationships shaped her career aspirations and motivated her to pursue education across multiple institutions—from community college and North Central College for her undergraduate degree, to an Education master’s degree from Alverno College and a Political Science master’s degree from Marquette University, and now her Ph.D. in Educational Leadership and Policy Analysis at the University of Wisconsin-Madison.

After moving to Milwaukee, Gabbi taught high school special education in the Milwaukee Public School system while serving as a debate coach and tutor. Now pursuing her doctorate full-time, she continues her commitment to education as a substitute teacher and Academic Coach, with the ultimate goal of becoming a K-12 administrator.

As a transplant to Milwaukee, getting involved with Big Brothers Big Sisters was Gabbi’s way to connect with her new community. “Showing up, listening, and caring for my new community was the way in which I could help support and uplift my new home,” she explains. Through the Mentor 2.0 program, she was matched with Guadalupe (‘Lupe’), and their connection was immediate.

Despite being warned that Lupe was “timid” and “shy,” Gabbi discovered quite the opposite. “The first time I met her, she spoke for almost 1 hour and 15 minutes straight!” This instant connection exemplified what would become a deep, trusting relationship.

One highlight of their partnership was a college visit to Marquette University, where Gabbi was working as a teaching assistant. Lupe still calls it the “VIP Tour,” experiencing college life firsthand—from lecture halls to dining halls to meeting current students. Over three years, Gabbi has watched Lupe grow into “an incredibly resilient young woman” who successfully graduated from high school.

The relationship has been mutually transformative. During health challenges, Gabbi’s mentorship with Lupe provided something positive to look forward to. Winning Match of the Year has been a “surreal experience,” providing opportunities like appearing on the Little BIG Chats Podcast and reinforcing the importance of community involvement.

Although she now lives in Madison for her doctoral program, Gabbi still considers Milwaukee her second home. Her experience there—teaching in Milwaukee Public Schools, participating in Teach for America, attending universities, and mentoring through Big Brothers Big Sisters—has shown her “some of the best of what Milwaukee has to offer.”

Looking toward Milwaukee’s future, Gabbi’s vision is rooted in her experience as a special educator. She wants to see the city continue fighting for educational equity, particularly for students with disabilities. Her doctoral research will focus on Milwaukee, ensuring her continued connection to the community that welcomed her.

Through Big Brothers Big Sisters, Gabbi discovered that giving back isn’t just about helping others—it’s about being part of something bigger and contributing to the greater good of the community that became her home.