Wintley A. Phipps

The moment that sparked my passion

I am a minister and successful gospel performer, so to give back, in my early 40s I started doing prison ministry. It was there I learned the stats on intergenerational incarceration, and realized I had to do something so I wouldn’t be coming back later to minister to the grown kids of the people I was meeting behind bars. Further tipping the scales: A pregnant woman I met in one prison turned out to be my wife’s niece. When we examined my wife’s family tree, we realized all seven of her siblings, plus many of their children, had been incarcerated. My wife escaped that fate because she was mentored by a neighboring family. I knew I needed to bring this care to other kids.

Why my approach is unique

Founded in 1998, we are one of the nation’s oldest school-based mentoring and after-school programs targeting children of incarcerated parents and other vulnerable youth. We currently serve 700 students, from elementary to high school age, in 15 schools in eight cities around the U.S. Unlike most after-school programs that focus only on academics or recreation, we support the whole child. When they come to our program, located in their own school, we help with homework and other academics, teach them the positive character traits necessary for a successful life, and work to build their dreams, because unless you see a doctor or a pilot, you can’t picture that for yourself. Finally, adult mentors in the community meet one-on-one each week, and often become lifelong friends.

Advice to others who want to make a difference

In the nonprofit world, everything takes a long time, so you need a dogged determination to keep at it. You also need patience — one of the character traits we teach the kids. Finally, it helps to have faith, not only that things will work out, but also that in the end your efforts will be a blessing to both individuals and humanity at large. I always joke, though, that God has this thing about answering prayers at the 11th hour. After the recession in 2008, for example, our funds were so low we worried we might need to curtail some of our programming. It was right before things got that dire that Oprah Winfrey, a fan of my singing and a major supporter of our program, surprised me with a massive gift.

What I hope will be next

We’ve been blessed to be assisted by many great people, including senators and presidents. Along with our incredible staff of 45 people and our 350 community volunteers, this has enabled us to expand to the eight cities we work in now. But there are so many children in other parts of the country we haven’t gotten to yet. My dream is for Dream Academy to help the kids of incarcerated parents everywhere be able to dream of their own bright future — and to have the tools to make it so.