Wintley Phipps: A Man of Charisma and Faith

He has done more than just sing about his love of Christ. He has tried to love like Christ.

The U.S. Dream Academy's Wintley Phipps, Guideposts

Charisma. It’s one of those things that’s hard to define but you know it when you see it and I saw it in the person of Wintley Phipps, who paid a visit to our offices in New York the other day.

Wintley truly lights up a room with both his physical and metaphysical presence. Knowing him only as one of the great gospel singers of our time, I fully expected a man of faith. What I didn’t know was the incredible way he has used the blessing of his success and fame to reach out and help others, especially children whose parents are incarcerated. He has done more than just sing about his love of Christ. He has tried to love like Christ.

It began with a concert he gave at a prison back in the mid-’90s. He was struck by the sad-eyed children visiting their incarcerated parents, their seeming loss of hope. He learned that the children of inmates are many times more likely to end up in jail themselves. It is a vicious cycle, one he hoped to help break. In 1998 he formed the U.S. Dream Academy, a nonprofit organization that focuses on these children at risk, supporting them academically. A solid education, Wintley realized, is the best way to break the chain, and so many of these children struggled in school, fell through the cracks and usually dropped out. A diploma was the best defense against following down the path of an incarcerated parent.

It didn’t hurt that Wintley had met a lot of famous and influential people who could help him get his program off the ground. And he has great stories to tell about them. He seems to have performed for and befriended every U.S. president in his adult life along with some of the great stars of our time.

My favorite of Wintley’s stories goes back to when he was still an up-and-coming gospel singer performing for a local news station in Baltimore. After he was through, a nervous young reporter shyly approached him. She said she was about to lose her job at the station and was in despair over the direction her life would take. “I thought you were someone I could pray with,” she said. She and Wintley held hands and bowed their heads. Then Wintley told her that God had given him the distinct impression that she would go on to great success in her career and touch the lives of millions and that he would continue to pray for her.

That nervous young reporter was Oprah Winfrey and she never forgot Wintley’s prayers. Today she is one of his biggest supporters. My impression is he has her on speed dial, along with a couple of presidents. I stared at his iPhone as if it were famous.

The big project Wintley has going right now is the Dream Academy’s Read to Achieve Read-a-thon. He wants kids not just to read but also to fall in love with reading. Reading comprehension is the key to educational success in the early grades. To that end, 600 students will be logging 2,400 minutes of reading each over the next two months. The goal is to reach a million combined minutes by December 20 and raise money for the Dream Academy’s critical afterschool programs for children of incarcerated parents.

I was sorry when Wintley finally stood to be on his way. I could have listened to his wonderful stories—and that beautiful, sonorous voice—all day. He asked if I would be kind enough to mention the Read to Achieve Read-a-thon in my blog. I have. Not out of kindness but out of sheer admiration.

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