Kenneth Roland

KENNETH “KENNY” ROLAND, SR., was born on April 23, 1949, in Chicago, Illinois, to the late Clorine and Richard Roland, Sr. He was the sixth of eight children and was born as a twin to his beloved sister, Kneater Roland, whom he cherished deeply. The two shared a life-long bond and were inseparable until her passing in 2019. Her loss profoundly affected him, as he often felt that a part of him went with her. In addition to his sister, Kenneth was preceded in death by his daughter, Yolanda Brandy; two grandsons, Anthony Terrell Moton, Sr., and Martell Winton; one great-grandson, Anthony Terrell Moton III (“AJ”); four brothers, Earl Williams, Roy Williams, Richard Roland, Jr., and Keith Roland, Sr.; and another sister, Judith Roland. Kenny was known as a fun-loving, outspoken, and warm-hearted man who spoke his mind and freely offered wisdom to those around him. One of his familiar sayings was: “Don’t worry about that, man—don’t worry about that.” His humor, honesty, and presence left a lasting impression on everyone who knew him. LOVE AND FAMILY: In May 1962, at just thirteen years old, Kenny met Pamela, who was twelve at the time. Their youthful friendship grew into a life-long love. Together, they learned about life, love, and commitment. They welcomed two daughters, Yolanda “Dee Dee” and Angela “Angie”; two sons, Kenneth Jr. “Boo” and LaDaryl, Sr., “Ding” who became the center of their world. Wanting to serve his country and provide a better future for his family, Kenny proposed to Pam, and they were married on October 2, 1968—a friendship and love that lasted a lifetime. Together or apart, whenever there was a need for help of any kind, whether it was conversation, medical care, bills, or any business that needed to be taken care of, they were a team. They knew that they could always rely on each other. When Kenny’s health began to fail him, he knew that he could call Pam to help him out. When he needed groceries, to get to the pharmacy, or his appointments. When she needed transportation, he was there. He would come to pick her up and when he got there he would get out of the driver’s seat…and yes, she drove wherever they needed to go, without hesitation. She took care of Kenny as if they were never apart. “Always and Forever through Eternity” was their saying from the time they fell in love. Kenneth met Ruth on the North side of Chicago. They began a partnership and friendship. in which Ruth cared for Kenneth up until his passing. MUSIC AND FRIENDSHIP: Music was one of Kenneth’s greatest passions. He was a gifted singer nd a proud member of the vocal group The Deltours, recording songs such as “Blind Girl” and “Sweet and Lovely Girl.” Whether performing on stage or harmonizing on Chicago street corners, Kenny shared his voice with joy and soul. Some of his most treasured memories were singing alongside his twin sister Kneater. He also maintained life-long friendships with fellow musicians, his C.T.A. coworkers, and his Farragut High School Reunion family, all of whom held a special place in his heart. EDUCATION AND SERVICE: Kenneth attended Robert Burns Elementary School, and later attended Farragut High School. He remained deeply connected to his alma mater, faithfully attending reunions and volunteering, often humorously serving as “security,” directing traffic and watching over everyone. Kenneth proudly served in the United States Army, demonstrating his commitment to duty, discipline, and country. After his military service, he worked in maintenance for the Chicago Transit Authority (CTA), where he was respected for his strong work ethic and reliability. CHARACTER AND LEGACY: Kenneth was a man of resilience, quiet wisdom, a strong voice towards discipleship, and deep love for others. He had a generous heart, valued friendship, and found joy in simple pleasures, especially his favorite Family Dollar sandwich cookies. Above all, Kenneth cherished his family. He was a proud father, grandfather, and great grandfather whose love and guidance will live on for generations. His legacy of kindness, music, loyalty, and service will forever remain in the hearts of those who knew him. Kenneth Roland, Sr., will be deeply missed but lovingly remembered. His spirit, laughter, and love will continue to shine through his family and friends. Kenneth is survived by his devoted wife, Pamela Roland of Chicago, IL; his loving children Angela Roland of Chicago, IL; Kenneth Roland, Jr. (Cherise) of Minneapolis, MN; and LaDaryl Roland, Sr. of Glendale, AZ; and son-in-law George Brandy of Chicago, IL. twenty grandchildren, twenty-four great-grandchildren, and two great-great-grandchildren; one sister, He is also survived by his longtime partner and friend Ruth Afioga Tulele; one sister, Gloria Willis of Las Vegas, NV; brothers-in-law Danny Mitchell (Brenda) and Walter Mitchell; sisters in-law Monica Roland, Alice Tanksley, Rose Wofford, Mary Mitchell, and Carrie Roland; aunt in-law Mrs. Pearlie Hills; and a host of nieces, nephews, cousins, and friends. A special friendship with Mayor Harvey of Bellwood, IL

To send flowers to the family or plant a tree in memory of Kenneth Roland, please visit our floral store.