Wintley Phipps Is Inspiring Dreams by Keeping at-Risk Youths Out of Prison

Wintley Phipps performs with the Dream Kids and the Takoma Academy Chorale at the U.S. Dream Academy's 15th annual Power of a Dream Gala on May 3, 2016, in Washington, D.C.
U.S. Dream Academy via Twitter

Wintley Phipps is a force of nature, standing amid a children’s choir, belting out the gospel classic “He’s Got the Whole World in His Hands.” The performance, at Tuesday night’s 15th annual Power of a Dream Gala, was for a glittering crowd gathered to share his passion for keeping at-risk children out of prison.

“When you believe in what you are doing with all of your heart, you put your hand to the wheel,” Phipps says. “You’re running on passion and vision.”


On Tuesday night at the Washington Renaissance Hotel in D.C., the Grammy-nominated Phipps shared that passion with like-minded people, who came to support the U.S. Dream Academy, which he founded in 1998. The national after-school program is aimed at breaking the cycle of children following their incarcerated parents into prison through education, mentoring and technology-driven activities. It currently operates in seven cities, including Orlando, Fla., Salt Lake City and Washington, D.C.

For Phipps, the motivation to create the project was very personal.

“All of my wife’s brothers and sisters have been incarcerated at some point in their lives. Her older sister had six children, and five have been in prison,” Phipps explains. “You look at other kids who you know, without intervention, without help, many of them will follow their parents down that same road unless they get the kind of encouragement and guidance and motivation my wife got from the family down the street.”

Phipps’ wife, Linda Galloway, was mentored by a neighborhood Christian family who sent her away to school, which allowed her to eventually become a registered nurse. Phipps says that the U.S. Dream Academy, through a program that involves everything from mentoring to academic skill building and character building, helps over 700 kids per day and has touched the lives of thousands. He cites the story of two twins from Philadelphia: Kwame and Quentin.

“Their mother lived in Philadelphia, and while the father was incarcerated, she had twins. Those two twin black boys—both together—failed the first grade. The principal of the school reached out, and they’ve been part of our program for about six years,” Phipps says. “We see the tensions go away. Their conduct is awesome, and their academics improved significantly, and so these twin boys … we know they’ve got a shot.”


At the ceremony Tuesday night, Jaime Casap, global education evangelist at Google, received the President’s Award for his work on education; Rep. Bobby Scott (D-Va.) received the Legacy Award for his work with children and criminal-justice reform; and Jarrett Adams received the MLK Jr. Award. Adams was wrongfully convicted of sexual assault at the age of 17 and sentenced to 28 years in prison. He was released after 10 years after battling for justice, graduated from the Loyola University Chicago School of Law and founded his own organization, Life After Justice. Adams says that he’s focused on helping people who have come home from prison and need access to education and a trade so that they can provide for themselves.

“We help someone all the way from being able to tie a Windsor knot for an interview to how to balance a checkbook,” Adams says. “If you provide people with the education and opportunity to provide for themselves, what reason would they have to rob and kill and steal?”


Adams says that people who read about his success should understand that his story is amazing, but it can be duplicated. He stresses, however, that it was hard work and that education is key to everyone’s success.

“Right now you have everyone floating the banner while they’re running a campaign of, ‘We’re interested in criminal-justice reform,’” Adams explains. “The only way you do that is that you provide access to education to both people who you want to keep from going in and also the people who are in and will get out.”


“This is very special, in a tough election year … where real issues are being heard and the whole school-to-prison pipeline has been brought up by many of the candidates,” says actor Laz Alonso, who was a co-host for the event and is currently starring in NBC’s The Mysteries of Laura. “Back in the day, a lot of candidates, because of their own political affiliations, thought they could just walk into a nomination or get the black vote. Oh no, no … you have to earn our vote, and this is what we want because … these are areas of the community that aren’t being serviced.”

Rep. Scott, who says that he is honored to have received an award from an organization that focuses on at-risk children, notes that this is a much better way of dealing with crime than the traditional bidding wars that erupt over who can impose the harshest sentence.


“Traditionally, we just load up prisons, and we’ve followed that strategy to the point that it is counterproductive,” Scott says. “We lock up so many people now that Pew Research has calculated that we are actually adding to crime because we are messing up so many families.”

Scott says that there are several pieces of legislation being considered on Capitol Hill that could help, including the Youth PROMISE Act, to help get young people on the right track, and the SAFE Justice Act, which would reduce mandatory minimums.


Phipps cites statistics showing that 60 percent of black boys in the U.S. who don’t graduate from high school will be in prison by age 30. That’s among the problems the U.S. Dream Academy is trying to address.

“We don’t really know why school success helps the way it does—whether it is the sense of self-worth and self-esteem it fosters,” Phipps says, “but it helps to inspire dreams and success.”

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