Robert "Bobby" Leslie Pillow Olmsted

Robert Leslie Pillow “Bobby” Olmsted, 84, passed away peacefully on Sunday, June 1, 2025, at the University of Mississippi Medical Center, surrounded by family after a brief illness. Graveside services are at 11:00 A.M on Saturday, June 7, at the Scales-Pillow Family Cemetery in Greenwood. Visitation is at 9:30 A.M. Saturday at First Presbyterian Church. 

Bobby was born to Dr. John Gerald Maurice Olmsted and Helen Pillow Olmsted in Hartford, CT, and moved to Greenwood with his family in 1948. He graduated from Greenwood High School and later attended Mississippi State University, where he was a member of Sigma Chi. He proudly served in the Air National Guard and later began his career at Ram Golf in Pontotoc, MS. He returned to Greenwood, where he resided on Elmwood Plantation for most of his life. He later owned and operated Greenwood Lumber Company and was held in high regard by all of his employees. After retiring from Greenwood Lumber Company, he worked with his daughter, Lessley, at the Indoor Garden in various capacities for 18 years. His favorite job of all was being a “professional grandfather,” as he called himself. Bobby was affectionately known as “Bop” to his granddaughters, Helen and Rachel, as well as almost everyone who knew him. He was deeply invested in the lives of his grandchildren and was most commonly seen in the Pillow Academy carpool line or helping them with their homework after school. 

He was a fourth-generation member of First Presbyterian Church of Greenwood. He was also a member of the Rotary Club, where he was recognized as a Paul Harris fellow. Bobby loved spending time outdoors, especially in his well-known water gardens, and achieved the status of certified Master Gardener. 

Bop was a loving husband, father, and grandfather to his family and a cherished friend to many. He will be deeply missed by all who knew him and will be remembered by his bright smile and cheery disposition. 

Bobby is preceded in death by his parents. He is survived by the love of his life and wife of 57 years, Gloria Randle Olmsted; his daughter, Lessley Olmsted Singleton (Mark) of Greenwood; two granddaughters, Helen Olmsted Singleton of Jackson, Rachel McLean Singleton of Greenwood, and two sisters, Wendy White of Tuscaloosa, AL, and Pam Hull of Cleveland, MS. 

Pallbearers will be Mark Singleton, Neil Hubbard, Matthew Hicks, Reese Pillow, IV, Charlie Swayze, III, and Taylor Calhoun. Honorary pallbearers are Webb Franklin, Charlie Swayze, Jr., Fisher Southworth, Sr., Bob Knight, Fred Carl, Silvester Freeman, and Howard Marye. 

The family would like to extend a special thanks to the ladies of Indywood Glen. Memorials may be made to St. Jude Children’s Research Hospital or the Leflore County Humane Society.

The Scales-Pillow Family Cemetery is located at 2905 River Road Extended in Greenwood, MS. 

Greenwood Delta Funeral Home (www.greenwooddeltafh.com) is in charge of arrangements. 

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