William "Bailey" Gregory

William Bailey Gregory, a vibrant spirit who brought joy and laughter to all who knew him, left this world far too soon on December 16, 2024,near Cherryvale, Kansas as a result of injuries sustained in an auto accident. Bailey was born on April 23, 1994, in Osage Beach, Missouri, to Jerry Gregory and Ronda (McAlexander) Matney. Bailey captured hearts with his charismatic charm and infectious smile, living life to the fullest until the very end. 

Bailey wasn’t just a son or a brother; he was a loving father to his pride and joy, William Bailey Gregory, Jr., whose well-being and happiness were his highest priorities. Being a dad was far and away his greatest accomplishment, and he would have done absolutely anything for his little guy. Even though he and William's mother, Amanda Hodges, had gone their separate ways, they shared the same commitment to ensuring their son felt loved and supported. 

Growing up, Bailey’s journey led him to Lebanon, Missouri and then to Altamont, Kansas, where he attended Labette High School and graduated in 2013. During those teenage years, he shone brightly in theater and music, always entertaining everyone around him. After school, he found a fulfilling career at Machinery Maintenance in Parsons, Kansas, where he often quipped that he was “building America one curb at a time.” he loved working with his hands and mastering the art of concrete work. 

Outside of his professional life, Bailey was a true artist at heart. He found joy in playing Dominos and was often spotted on the golf course hanging out with his brothers. He used his creativity in creating pottery though it was not quite what you'd see in a gallery, each creation was full of heart and a reflection of his fun-loving spirit. Sunday afternoons were reserved for football, where you could find him glued to the screen, engaging in lengthy discussions about the game with his Mawmaw. If the KC Chiefs or the Carolina Panthers were playing, you could count on their conversations to stretch on! Though he had never been to Hawaii you would have thought he was a resident with the numerous Hawaiian shirts he owned and wore. If he wasn’t in his favorite Hawaiian shirt he was in a plaid flannel. 

Bailey’s relationship with his family was nothing short of extraordinary. He was a constant source of encouragement for his younger brother Owen, sending uplifting texts every day. He cherished his role as Uncle Buddy to his nieces and nephews, who adored him for his playful spirit and kind nature. Long conversations and shared laughs were the backbone of his family time, as Bailey made it a point to connect deeply with each loved one. 

He is survived by his son William Bailey Gregory Jr., dad and stepmom, Jerry and Michelle Gregory; his mom and stepdad, Ronda and Joe Matney; girlfriend Sarah Gordon; siblings Ethan Gregory and his wife Katie, Taylor Gregory and his wife Caitlin, Owen Dennis, and Abby Dennis; his grandma, Barbara McAlexander; and step grandparents William and Candy Hill; a host of nieces, nephews and friends. He was preceded in death by his fraternal grandparents Junior Dale Gregory and Barbara Curlis; maternal grandpa Ronald McAlexander. 

 Bailey’s vibrant spirit, infectious laugh, and compassionate heart will be missed deeply by all who had the privilege of knowing him. A funeral service to celebrate Bailey’s incredible life will be held on December 23, 2024, where the family has request you wear your favorite Hawaiian Shirt or comfy Flannel in honor of Bailey. Services will begin at 1:00 PM at the Ford-Wulf-Bruns Chapel, 2405 Woodland Ave. in Coffeyville, Kansas. Graveside services will be held following the service at North Edna Cemetery. The family has requested memorial contributions to be made payable to William Bailey Gregory Jr. Education Fund. Contributions may be left in care of the chapel or left at Community National Bank. To leave a message of condolence or share a memory visit www.fordwulfbrunschapel.com