Wintley Phipps’ Singing Ministry Helps Set the Children of Prisoners Free

Wintley Phipps, the renowned Grammy-nominated gospel singer who has sung for the last six U.S. presidents, was deeply troubled. About 30 years ago, he had begun singing in prisons and was shaken by what he saw: young black men locked up, many of whom had children. He soon learned some shocking statistics:

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• 1 out of every 3 black men between the ages of 18 and 30 is in prison, on probation, or on parole.
• Between 60% and 70% of people in prison were born to people who ended up in prison.
• By the age of 30, 60% of African American boys that do not graduate from high school will be in prison.

Disturbed by these statistics and grieved by the inherent risk posed to children of incarcerated parents, Phipps wanted to do something to ensure that these youngsters could grasp a brighter future. He tapped experts from Princeton and the University of Michigan to examine the problem; the chaplain of the U.S. Senate was also on that committee. After two years, in 1998, the Dream Academy after-school program was born.

“A committee of experts determined that two interventions would be most effective,” Phipps says. “Increasing the density of caring, loving adults in these children’s lives; and academic tutoring.”

While ministering in the prison, Phipps felt as if he were on a black college campus. When asked why–were the men articulate, were they bright–he answered, “Bright? They were brilliant. But many of them had been caught in the inter-generational cycle of incarceration.” That was the cycle Phipps was determined to help break.

Now in operation for nearly 20 years, Dream Academy locations–12 total–are found in seven cities. The program is built on three pillars: character building, dream building, and skill building; character is first, Phipps says, noting that employers “hire for skills, but fire for [lack of] character.”

Phipps has identified eight dimensions to character:

1. Strong faith: the ability to believe in what you cannot see.
2. Moral integrity and goodness.
3. Love of learning, love of knowledge, wisdom (knowing how to apply knowledge).
4. Self-control: If you can’t walk away from something, you don’t own it; it owns you.
5. Patience: People of strong character are people who can hang in for the long haul. They don’t try get-rich-quick schemes.
6. Respect for what they hold sacred: people who don’t hold anything sacred aren’t safe.
7. Kindness.
8. The ability to love: choosing to be at your best when the other person is not at his or her best.

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