Andre Ra’Mone Winfrey

In Loving Celebration of the Life of Andre Ra’Mone Winfrey

“Well done, thou good and faithful servant.”                                                                                                                                                                                                                                                                                  — Matthew 25:21 (KJV)

Andre Ra’Mone Winfrey was born on November 13, 1969, to Henry Winfrey Jr. and Janice Winfrey. From the moment he entered this world, Andre carried a joyful spirit, a creative soul, and a heart full of love—gifts he shared freely with everyone blessed to know him.

Andre received his education at Phillips Elementary School and Parkman Middle School before graduating from Custer High School in 1989. During his high school years, he played basketball, displaying discipline, teamwork, and determination—traits that followed him throughout his life.

Andre was a gifted videographer with a deep passion for music and storytelling. He had a natural talent for capturing moments and turning them into lasting memories. Whether creating family videos, photographing life’s special occasions, or producing music videos with A-G-2-A-KE (88 Keyz, Mac Fee, and G-Mone) and Polo World, Andre used his creativity to uplift others and celebrate artistry. His work reflected his eye for detail, love for music, and joy for life.

Known for his humor and love of good food, Andre also found joy at the grill. He proudly shared photos of his culinary creations and often joked—confidently—that he was better than Bobby Flay. His laughter was contagious, his jokes unforgettable, and his presence always brought warmth to any gathering. Andre would do anything for those he loved, and his kindness left a lasting imprint on countless lives.

At the core of Andre’s life was his big heart. He found purpose in serving others as a devoted caretaker for adults with disabilities, offering compassion, patience, and dignity in all he did. Andre lived out his faith through action, always willing to go above and beyond for those he loved and cared for.

On June 27, 1997, Andre was united in holy matrimony with the love of his life, Yolanda Douglas, at the Hilton Waikoloa Village in Hawaii. Their beautiful union of 28 years was blessed with an extraordinary son, Douglas Winfrey—whom Andre proudly described as amazing, highly favored, and compassionate. Andre took great pride in the man Douglas has become, and his love as a father was unwavering and evident.

Andre transitioned from labor to reward on January 8, 2026. He was preceded in death and joyfully welcomed into eternal rest by his grandfather, Henry (Papa) Winfrey Sr.;
grandmothers, Pearlie Winfrey and Dorothy Milton; and his beloved aunt, Sandra Lee Caruthers.

Andre leaves to celebrate his life and cherish his memory his devoted wife, Yolanda Winfrey; his beloved son, Douglas Winfrey; his brothers, Brandi (Tinnisha) Winfrey and Kelly (LaVonda) Winfrey; his nephews, Kelly Winfrey Jr., Jaiden Rhodes-Winfrey, and Mason Winfrey; his uncle, John (Sheila) Milton; along with a host of cousins, other relatives, and dear friends.

Andre lived fully, loved deeply, and served faithfully. His legacy is one of joy, creativity, compassion, and unwavering love. While we grieve his physical absence, we rejoice in knowing that his race is complete, his work is finished, and his soul now rests in the presence of the Lord.

“To be absent from the body is to be present with the Lord.”                                                                                                                                                                                                                                                      — 2 Corinthians 5:8

Andre Ra’Mone Winfrey will forever remain in our hearts, our memories, and our lives. His light continues to shine, and his love will never fade.

A Service will be held on Friday, January 23, 2026 at 6:00 PM at Christ the King Baptist Church, 7750 North 60th Street, Milwaukee, Wisconsin.