The first installment of MATC President Dr. Anthony Cruz’s Student Leadership Series kicked off this month. The series is aimed at exposing MATC students to leaders in our community, and specifically leaders who have made a big difference in underserved communities. On Wednesday, February 12, a conference room on the 6th floor of the M Building at the Downtown Campus was full of students who braved a winter storm for a chance to engage with two prominent leaders in our community: Gregory M. Wesley JD and Margaret Henningsen.
Wesley arrived in Milwaukee in 1997. He joined the national law firm Gonzalez Saggio & Harlan LLP before transitioning to the Medical College of Wisconsin in 2016. He serves as their inaugural Senior Vice President for Strategic Alliances and Business Development, later adding the role of Interim General Counsel. His work helped forge key partnerships and expand the Medical College’s impact.
In 2024, he became President and CEO of the Greater Milwaukee Foundation, Wisconsin’s largest community foundation and one of the first established in the world. Under his leadership, racial equity remains the Foundation’s guiding principle, shaping investments and strategies for social and economic change.
At the leadership event, Wesley spoke candidly about being an early investor in creating Legacy Bank and working with Henningsen on building the bank’s impact. He detailed his struggles and the adversity he encountered along the way – while encouraging students to stay ambitious. Wesley insisted that students not buy into the idea that college is unnecessary – while he recognized that some may be able to succeed without higher learning, he was adamant that “education is for everyone.”
The other speaker, Margaret Henningsen, co-founded Milwaukee’s Juneteenth Day celebration in 1971. It is now one of the nation’s longest-running and largest Juneteenth Day celebrations. Her vision helped revitalize what is now Martin Luther King Jr. Drive, strengthening Milwaukee’s commitment to honoring Black history and culture.
A champion for economic equity, she co-founded Legacy Bank in 1999 to serve Milwaukee’s underserved communities, particularly Black entrepreneurs and families. As one of the few Black-women-owned banks in the country, Legacy Bank provided critical financial resources to help build generational wealth where it was needed most.
A lifelong advocate, visionary, and change-maker, Henningsen’s leadership continues to inspire future generations, and after experiencing her wisdom today, there is no secret why. Henningsen spoke in-depth about growing up in a more segregated Milwaukee, and the changes she has witnessed in the past 70 years. One story that Henningsen told, that received rapturous applause, regarded her expulsion, and subsequent reinstatement at UW-Milwaukee. During the civil rights movement, Henningsen was participating in a movement on campus, when a student threw a chair at the group. Unsure of how to proceed, Henningsen threw the chair back – I could not retell the story in full and do it proper justice, but she ended the story by mentioning that the same student who threw the chair all those years ago, ended up being a major source of funding for Legacy Bank – she had turned an enemy into a lifelong friend, and she encouraged students to create these bonds, and to look for connections over differences.
