Wintley Phipps


By Markus WilliamsWintley-Phipps

Where shall I fly and where shall I be?
Someone planted a tree.
A tree they may never see.

Some could have thought that it was unlikely. Others might have thought it not realistic and reality says it was simply impossible. For Wintley Phipps his dreams were his constant companions, they were all he had. Years later, his dreams would have dreams of their own through the minds of those he helped to fly.

He was born in Trinidad to a family who would not be a candidate for a Norman Rockwell painting. His home life was a troubled one as his parents had an unhealthy relationship and he was tasked with learning to fly on his own. As a young boy on the island he would try to escape by transforming his beloved tricycle. This was not just any tricycle it was a window for his imagination. He would turn this tricycle on its side and use the wheels as a driving instrument. He was instantly able to imagine himself flying all over the world or driving throughout the island. He wanted to find meaning and significance in his life, a life that seemed to have no wings.

Rumor had it that Wintley’s father was planning to take a trip. This information was supposed to be classified as his father did not plan to return. He obtained his passport and a one way ticket to Canada. His mother found out about the plans and she decided to make plans of her own. She also got passports for herself and the kids and on the date of his scheduled departure she decided to show up ready to go. They all moved to Montreal Quebec where Wintley continued to dream. He enjoyed accompanying his father to the airport as they would see visitors off. While there he would grab luggage tags and stuff them into his pocket, once home he began to write his name on the tags dreaming of the places that he would one day travel.

As a young man he was attracted to music. He began to discover the power of the human voice as his very own rich communicative baritone instrument began to speak to individuals. One of those persons was a Catholic lady who would later become his first patron. One summer, after hearing about a school called Oakwood College he hitched a ride to Huntsville Alabama with high hopes of enrolling. He didn’t quite consider the concept of tuition, so when asked how he would pay for it he pulled out three hundred dollars and hoped for the best. It was beginning to look like his three hundred dollars was not going to take him very far when someone noticed in his file that he had a credit. His patron had heard he was planning to visit the school so she sent him money and this is what allowed him to get into school. As he considered what to study he looked around and saw that the only way he could serve the church and make a living was through preaching so he set out to study theology. He would later realize that it would be his music career that would open more doors providing him a wider audience of service. As he was preparing to leave the seminary he was in conversation with his dear patron. She happened to ask him when his album was coming out. He laughed, as that was not something he had considered it was a dream with no wings. He told her what it would take to properly record an album and how much it would cost. She gave him the money and this is how he recorded his first album. He entered a career that would have him serving as pastor, recording artist and traveling around the world to every country. He has journeyed far from his beginnings and his dreams were no longer make believe moments with his tricycle.

By most people’s standards he had achieved what would be considered success. He was a successful recording artist, Grammy nominee, presidential confidant with many notable performances. But his story was waiting for one of the most important chapters to be written. His dreams needed to continue with the next generation. He understood what it means to be born in a family caught in an unhealthy cycle so in 1998 he founded the U.S. Dream Academy.

This nonprofit organization targets at risk children and youth living in high crime and high poverty areas who also have parents serving time behind bars. The kids often don’t think they will live to be adults so they forget how to dream, and with forgetting they become vulnerable to losing the ability all together. The Dream Academy stands in the gap nurturing the whole child through character building, skill building and dream building. The most important part of the program is the caring loving adults who surround the kids.

Since 1998 they have grown into the operation of ten centers in eight different communities around the country including Baltimore, Washington D.C., Orlando and Memphis. They are called Dream Cities. The Dream Academy has captured the attention of President Bill Clinton, Oprah Winfrey and many other notable figures. They are changing lives as they empower their students to believe in themselves and succeed. No matter their start it does not have to be their end. He believes that we are interwoven and interconnected requiring an organic participation. Without it, something vital is lost.

We celebrate you, Wintley Phipps, for your service to humanity. Caring enough to help and change the life of another human being is the greatest act that an individual can do. For so many students you have made an impossible dream come true.