Gwendolyn Jackson

Gwendolyn Jackson was born on September 28, 1959, to the loving union of Joseph and Julia Quinn Jackson. She often referred to herself as the misunderstood middle child in a lively house of seven siblings - Doris Jean “Faye”, Paul Anthony, Rosalind, and Derrick Reynold “Butch.” Her siblings LaDwenna Carol “Dean” and Vernon preceded her in death. Gwen grew up on Throop Street, where she and her siblings (along with her forever best friend Laureen) were known to stir up just the right amount of mischief. Whether it was engaging in a neighborhood street brawl or being chastised by an elderly neighbor for saying some not-so-nice words, Gwen was always in the midst of the action. A self-proclaimed bookworm, she’d stay up reading under the covers with a flashlight long after lights out and often got caught! That curiosity and love of words followed her into adulthood, shaping her quick wit, sharp tongue, and impressive vocabulary. Trust me, you would lose every debate! She graduated from John W. Cook Elementary and Calumet High School. She met her great love, Terry “T,” at a club when she was 15 - a place she had no business being! Their love brought forth her first child, Ivy Dacia Joi. Though their romantic relationship ended, their friendship endured for life. Terry remained a steady presence, helping co-parent Gwen’s second child, Ian Diamonte Jerome, whom she had from another relationship. Gwen gave her children the freedom to be who they were and encouraged them to speak their mind. For Ivy, she was a confidant, travel partner, and built-in safety net. Where Ivy is more reserved, Gwen was magnetic and full of energy - together, they were a perfect balance. For Ian, her “king,” they were kindred spirits that shared everything from a deep love of Prince to a mutual obsession with great music. Gwen always seemed to know what her son needed before he could ask. She was his compass, his peace, his teacher - and his heart. Gwen worked at Humiston-Keeling before joining the United States Postal Service (USPS) as a mail carrier. Known to her co-workers as a firecracker who didn’t back down from a fight for fairness, Gwen proudly served the USPS for nearly 30 years before retiring in 2023. In retirement she accomplished one of her biggest dreams - becoming a first time homeowner. She enjoyed adorning her home in her own style, gardening, cooking, and caring for her granddaughter. Above all else, her greatest joy came from being YaYa to her “grand-ladies,” Thierry and Kayden. She was their biggest cheerleader, their motivator, and their fierce protector. She loved talking about them to anyone who would listen. Her love for them was loud, proud, and unconditional. In January 2025, Gwen received a heartbreaking diagnosis: bladder cancer, complicated by severe kidney disease. Though she fought courageously, she suffered a series of strokes in June. On July 4th, 2025 — fittingly, Independence Day — she gained her freedom from pain and transitioned peacefully into eternal rest. While our hearts are heavy, we take comfort in knowing she is reunited with her parents and her beloved sister Dean. We hold tight to our faith that to be absent from the body is to be present with the Lord. Gwendolyn Jackson leaves behind a legacy of love, laughter, strength, and spirit. She is survived by her two children: Ivy and Ian (Tierra); six grandchildren: Thierry Noir, Zainab, Xenobia, Evan, Kayden DeVaughn, and Taylor; four siblings: Faye, Paul (Regina), Ros, and Butch; her son-in-love Navarro; and a large extended family of nieces, nephews, cousins, in-laws, and cherished friends.

Gwendolyn Jackson

September 28, 1959 - July 4, 2025