Robert Leland Headley

Robert Leland Headley obituary, Bloomington, IN

Robert Leland Headley

Robert Headley Obituary

Obituary published on Legacy.com by Allen Funeral Home and Crematory on Oct. 20, 2025.

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Robert "Bob" Headley, 58, of Bloomington, IN, passed away peacefully at home on Wednesday, October 16, 2025. He was born in East Liverpool, OH, on July 11, 1967, to Janet (Dunn) Powell and Wallace "Bill" Headley.
Bob was a proud U.S. Army veteran, serving his country with honor and dedication. His time in the Army instilled in him a lifelong sense of discipline, loyalty, and service to others, qualities that he carried into every aspect of his life.
He was known not only for his service but also for his sharp wit and great sense of humor, always ready with a quick comeback or a story that brought laughter to those around him. Bob found joy in life's simple pleasures, quiet evenings at home, time spent with family, and peaceful days with a fishing pole in hand.
For more than 20 years, Bob proudly maintained the horse racetrack at Presque Isle Downs Casino as the Track Maintenance Supervisor. His hard work, dedication, and good-natured personality earned him the deep respect of his coworkers and friends. He took great pride in his work and in the lasting relationships he built along the way. In recent years, he worked at Novo Nordisk as a manager, where he led his team to success while continuing to build meaningful friendships.
Bob will be lovingly remembered by his wife, Robin McMillan-Headley; his children, Bobby (Lydia) Headley, Toshua Moore, Jessica Edwards, and Dylan (Rosetta) Shields; his grandchildren, Madi, Anthony, Tristan, Sofia, Aria, Mila, Wrenley, and Arlo; his mother, Janet Powell; and his siblings, Jim (Leanne) Headley, Elizabeth (Brian) Edenfield, Clyde (Kimberly) Powell, Chris (Lisa) Powell, Clay Powell, Cindy Powell, Cheryl (Ron) Powell, and Trish (Matt) Davis. He will also be deeply missed by many extended family members and friends who were fortunate to share in his life.
Bob's humor, love, and warmth will live on in the hearts of all who knew him.

To plant trees in memory, please visit the Sympathy Store.

Allen Funeral Home and Crematory

4155 South Old State Road 37, Bloomington, IN 47401-7483

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