Wintley has performed for American Presidents Jimmy Carter, Ronald Reagan, George H.W. Bush, Bill Clinton, George W. Bush and Barack Obama at several National Prayer Breakfast events and other distinguished celebrations.
He performed for: the 1984, and 1988 National Democratic Conventions, Rosa Parks' 77th Birthday gala at the Kennedy Center,Mother Teresa of Calcutta, and President Nelson Mandela. He has appeared on various programs such as the Dr. Martin Luther King, Jr. television special, Dr. Robert Schuller's Hour of Power Telecast, the Billy Graham Crusades, at the Vatican, was guest soloist at Diana Ross' wedding ceremony in Switzerland, Saturday Night Live, Soul Train, and The Oprah Winfrey Show. He has also conducted lectures in Europe, Australia, Asia, Africa and North and South America.
Wintley was selected by Oprah Winfrey to offer musical interpretations for her week-long coverage of the ''9/11'' tragedy and was asked to pen a special prayer for her to deliver in tribute to the lives lost. He has met President Nelson Mandela of South Africa; performed for the 2005 pre-inaugural swearing-in ceremony of President George Bush. Wintley was nominated for Grammy Awards in 1988 and 1989. He is the author of The Power of A Dream (1996), founder of Songs of Freedom Publishing Company and Coral Records Recording Company.
Wintley attended Kingsway College, a Seventh-day Adventist Christian Academy, and later Oakwood University in Huntsville, Alabama where he received a Bachelors of Arts degree in Theology. Phipps would later go on to earn a Masters of Divinity degree from Andrews University in Berrien Springs, Michigan. Wintley served as senior pastor to several churches in the Washington, D.C. metropolitan area, including the Capitol Hill and Seabrook Seventh-Day Adventist Churches. He currently serves as Pastor of the Palm Bay Seventh-day Adventist Church in Palm Bay, Florida.
In 1998, Wintley founded and created the U.S. Dream Academy, Inc., a non-profit organization dedicated to providing a values-based, interactive, tutorial and remedial education program targeted at children and youth-at-risk through community Family Learning Centers located in various states. Seeing a need, Phipps wanted something to help break the cycle he saw played out so many times in his own family.