Gary Headley, age 78, passed away on Wednesday, September 15th.

Gary was born in Vienna, West Virginia in 1943 to the late Burl and Fern Headley. He served in the Air Force for four years as an air traffic control operator. He was awarded the Good Conduct Medal and the Expeditionary Medal. He graduated college with a Bachelor’s degree in business. He worked for Nationwide Insurance, quickly advancing into management. From there, Gary opened up his own agency, Headley Insurance, in Lakeland, Florida. After a successful career, he retired and was awarded an honorary PhD.

Because of Gary’s love for music, he and his wife Patty established Classy Music Live, where they performed throughout the southeastern United States for businesses, nursing homes, and many charitable organizations.
Gary loved the Lakeland community. He supported many charities and was an active member of Life Point Church.

Mr. Headley is preceded in death by his daughter Kim Fields.

Mr. Headley is survived by his loving wife of 18 years, Patty Headley; brothers Steve Headley (Carol), Phil Headley (Libby); Children, Scott Headley (Shari), Paul Headley (Angie); Step-children, Stacie Tollett (Chris), Christie Schwichtenberg, Stephanie Schwichtenberg; Grandchildren, Nathan Montgomery, Sarah Montgomery, Joshua Headley, Cole Headley, Josie Headley, Brayden Tollett, Oliver Schwichtenberg, Justin Fields Jr, Madalyn Fields, and 3 Great-grandchildren.

A funeral service will be held in Gary’s honor on Tuesday, September 21, 2021 at Life Point Church (5140 Bailey Road Mulberry, Florida 33860). Visitation will be at 9:30 a.m., followed by a service at 10 a.m.. Condolences may be sent to the family at Gentry-Morrison Funeral Homes.

“Aim High…Fly-Fight-Win”

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