Vondale Eugene Singleton Sr. Builds a Legacy of Mentorship
Born on the South Side of Chicago in the historic Ida B. Wells Homes housing projects, Vondale Eugene Singleton Sr. understands firsthand what it means to overcome adversity. Raised amid challenging circumstances, he defied the odds to become a first-generation college graduate, earning both his Bachelor’s and Master’s degrees from Oral Roberts University. He later received an honorary doctorate from Trinity International University.
Singleton credits much of his success to his mentor, Steven Robertson, who he says “invested sacrificially” in him and helped shape the man he is today. That investment sparked a lifelong commitment to ensuring other young men receive the same guidance and opportunity.
For more than 21 years, Singleton has worked in primary, secondary, and higher education as both a teacher and administrator. His leadership experience includes roles within the KIPP network and the Noble Network of Charter Schools, where he founded CHAMPS Mentoring. He now serves as Backbone Director for My
Brother’s Keeper Chicago (MBK Chicago), part of the broader Obama Foundation initiative focused on creating pathways of opportunity for boys and young men of color.
Singleton’s philosophy is simple yet powerful: “Salvation plus education is an unbeatable combination.”
Breaking Barriers and Redefining Narratives
Singleton’s early life was marked by hardship. He lost his mother at 14 and witnessed his father struggle with addiction and incarceration. Rather than becoming defined by circumstance, he chose faith, discipline, and accountability.
“Mentors poured life into me and helped me see my purpose,” he says. “When you believe you are Born 2 Win, you begin to live differently.” That belief became the foundation for CHAMPS Mentoring, a Gold-Star Award-winning program designed to provide structure, leadership development, mental health support, and college and career exposure for boys and young men of color.
Influences and Inspiration
Throughout his journey, Singleton was shaped by influential leaders and thinkers. In addition to Steven Robertson, spiritual guidance came from Pastor Clarence Boyd, Pastor Corey Brooks, and Pastor John Hannah. Motivational speaker Eric Thomas inspired his “one percent mindset,” while business leaders Larry Miller and Howard H. White of Jordan Brand modeled leadership rooted in legacy and excellence.
A Legacy of Impact
Singleton considers his greatest achievement to be personal: being a present father and husband. Professionally, he has received numerous honors, including recognition as a Chicago Defender Men of Excellence honoree and a mayoral proclamation recognizing ten years of CHAMPS service.
To date, CHAMPS Mentoring has served more than 12,000 young men across Chicago and cities nationwide. Participants have gone on to graduate from institutions such as Morehouse College and Northern Illinois University with scholarships, becoming entrepreneurs, engineers, and mentors themselves.
The organization now focuses on long-term sustainability, including plans for a permanent CHAMPS headquarters to serve future generations.
Overcoming Barriers
Singleton has faced poverty, grief, limited resources, skepticism, and the ongoing funding challenges of nonprofit leadership. Yet through partnerships, faith, discipline, and documented impact, he has continued to expand opportunities for the young men he serves. “What keeps me motivated is seeing a mentee reach a goal he set for himself,” he says. “Watching Boys and Young Men of Color become fathers, leaders, and mentors, that’s the reward.”
One of the most heartwarming moments for Singleton is when former mentees return to guide the next generation, creating a cycle of leadership and empowerment. “Every young man is Born 2 Win when given structure, love, and opportunity,” he says. “Chicago’s future depends on how we invest in our youth today.”
For more information about CHAMPS Mentoring, visit www.champsmentoring.com.
