Lennie S. Riley
March 31, 1938— February 23, 2026
Chicago, IL
Lennie Riley ObituaryObituary published on Legacy.com by Winters Funeral Home on Mar. 3, 2026.Born to the late Mildred and T.J. Stephens, Sr. in Kosciusko, MS. Lennie was the eldest of 13 children, seven boys and six girls. Her brothers Bobby, Roosevelt and Ostranda preceded her in death. She stood tall in her siblings' eyes and was revered by all of them. Lennie was in charge when her mom and dad left home and she was known to throw a few punches when she felt like they weren't doing as she said.Lennie's Christian walk began at New Garden Baptist Church under the stewardship of Rev. Benjamin Watkins in Kosciusko. She continued her faith walk joining St. Paul M.B.C. under the stewardship of Rev. J.J. Taylor and New Faith Baptist Church under the stewardship of Rev. Dr. Howard Randolph.Lennie attended Attala County Training School (ACTS) graduating in 1956. A few years later ACTS became Tipton Street High School, home of the Bobcats. Lennie was a true Bobcat attending all the reunions with her other Bobcat sisters and brothers.After a two-year courtship, Lennie married the love of her life, Jimmy in 1957 and subsequently moved to Chicago, IL. From this union three children were born-Raymond, Angela and Randolph (who preceded her in death). Lennie also blended her bonus child, Marydell, into the family fold who also preceded Lennie in death. After the death of her dear cousin Ora, Lennie embraced Gwen and her family and became Mama and Granny to them. At the young age of 70, Lennie became a new mom, welcoming a bouncing baby girl, Triana, into the Riley household. Lennie loved being a mother, a role that she was devoted to and designed for. She also loved being a grandmother and great grandmother to her children's children.Lennie was a hardworking woman. Her work history began at Albert and Susie Bell's Cafe' on Beale Street in Kosciusko. She also worked at such notable places as Standard Brand, Brach's Candy Company and Jewel-Osco in Chicago. She put in a full workday, came home and prepared meals for her family and still found time to continue her education earning an Associate Degree from Kennedy King College. Her thirst for knowledge was only surpassed by her desire to better her and her children's lives. She was so proud when Angela graduated college and Randy became a police officer. Her children's accomplishments were her accomplishments.Lennie's life was a testament to love, resilience, and unwavering devotion to her family and friends. In Lennie Stephens-Riley everyone that touched her life knew that they had found a virtuous woman.Lennie leaves to cherish her precious memories her son, Raymond and daughters Angela (Marvin) and Triana; Daughter-in-law Rashonda, Sister-in-law Dora, Son-in-law Nathaniel, grandchildren Randolph Jr., Tiffany, Brittany, Juanita, Samantha, Bridgette, Joyce and Ronald and her bonus grandchildren Vincent, Alonzo, Malcolm, Orlecia, Sisters Mildred, Minnie Pearl, Carolyn, Armetta, Alberta (Anthony); brothers, William, T.J. (Sharon), James (Cloia), and Robert (Shirleen); many great grandchildren and a host of family, friends and extremely close acquaintances.PLACE OF SERVICE: Winters Funeral Home Chapel, Kosciusko, MSDATE OF SERVICE: Saturday 03/07/2026 at 10:00 a.m.INTERMENT: Parkway Cemetery, Kosciusko, MSVIEWING: Friday 03/06/2026 at 9:00 a.m. - 5:00 p.m.Send flowers to the service of Lennie S. RileyTo plant trees in memory, please visit the Sympathy Store.
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