It is with great sadness that we announce the passing of our beloved friend and family member Kregg Christopher Bailey.
Kregg Bailey 84, of Southern Pines, North Carolina, passed away on December 29, 2025 at St. Joseph of the Pines Health Center after a short illness. Kregg was born April 9, 1941, in Dowagiac, Michigan, to the late Glenn and Helen Everett Bailey. He was raised and lived most of his life in South Bend, Indiana, marrying his wife of 65 years, Gail Roe Bailey.
After completing design school, Kregg spent his career in the graphic design and advertising industry as an art director and business owner. In 1982 he started Kregg Bailey & Associates in Elkhart, Indiana. Then in 1986 in collaboration with his daughter, Michele Kastner, they established Bailey & Kastner, Inc. an advertising and graphic design firm. Kregg and Gail retired from the firm in 2008 and spent time at their homes in South Bend and Beulah, Michigan. Kregg’s hobby was architectural design. Throughout his life he designed many homes for friends and family as well his and Gail’s homes in Elkhart and Beulah. In 2017 he and Gail relocated to Southern Pines, North Carolina from northern Michigan to be close to family.
Kregg’s dry sense of humor and sharp wit were hallmarks of his personality, bringing laughter to those who knew him best. He took great joy in spending time with his grandchildren and great-grandchildren, moments he truly treasured.
He is survived by his wife Gail, daughter Michele (Steven) Kastner of Southern Pines, North Carolina, grandson Brandon (Tasha) Kastner of Mishawaka, Indiana, and grandson Ryan (Heather) Kastner of Carthage, as well as great-grandchildren Jack, Joseph, Emmi Lou and Josephine.
The family extends their heartfelt gratitude to the compassionate staff of St. Joseph of the Pines for their excellent care, kindness, and support during his recent stay.
In lieu of flowers, memorial contributions may be made in his name to St. Joseph of the Pines, in appreciation for the care he received.
Memorial Services will be held at a later date.
Services entrusted to Fry & Prickett Funeral Home.
Online condolences: PinesFunerals.com.
