Sidney Leonard Pipkin, Jr. (Sid) died at his home in Pensacola, Florida on Wednesday, February 18, 2026, following a diagnosis of esophageal cancer last fall. Sid is survived by his wife of 53 years, Anna Catherine Bryson Pipkin (Cathy); sons Chuck Brown, Mobile, Alabama; and Sidney Leonard Pipkin, III (Pip), Pensacola, Florida; sisters Sharon McCool, Madison, Mississippi; Nancy Claire White, Pontotoc, MIssissippi; brother Bobby Pipkin (Tracy) Tupelo, Mississippi; sister-in-law Debbie Pipkin, Little Rock, Arkansas; grandchildren Keighly Brown, Nicholas Brown, Dorothy Brown, Alena Brown, and Isabella Pipkin; great granddaughter Amani Brown.
Sid is preceded in death by his parents, Evelyn Campbell Pipkin, Sidney Leonard Pipkin, stepmother Nancy Marshall Pipkin; brother Barry Pipkin, and brothers-in-law Grady McCool and Walter White.
Sid was born in Memphis, Tennessee. His family moved to Tupelo, Mississippi in 1954. His favorite childhood memories are of his grandparents farm in Carrollton, Mississippi. He graduated from Tupelo High School in 1960. He joined the Air Force soon after graduation, earning Airman First Class rank, and worked as a radial engine mechanic while stationed in Hawaii. He served during a period of high alert due to the Cuban missile crisis. After leaving the Air Force, he began a more than 50-year career as a commercial pilot, flying for Jesco, Inc., Bancorp South (now Cadence Bank), and others. In 1992, Sid and Cathy bought and managed Tupelo Aero, the fixed base operator at Tupelo Regional Airport, and later launched a charter flight service.
Sid was an extraordinarily skilled pilot, whose career includes legendary tales of his steady, steely maneuvering his aircraft to safe landings, amid challenges that included severe weather, a failed engine in one instance, and other emergencies. He logged approximately 14,000 hours of flying before retiring in 2014.
Sid and Cathy met in 1971 while Cathy was living in Memphis. They married in 1973 and lived in Tupelo, before moving to Pensacola, Florida in 2016. He will be remembered for his deep devotion to Cathy. Sid was genuinely hilarious. His unique – and definitely colorful – sense of humor, often blended with pearls of wisdom, left a permanent impression on everyone he met. He was an avid Ole Miss football fan, known for sharing pointed strategic insights while watching a game. He displayed similar calm reasonableness on the golf course. Sid’s brother Bobby remarked, “Sid had the opportunity to fly to so many places, but his last flight was the best of all – the flight to heaven.”
Holland Funeral Directors-Tupelo Chapel will be announcing plans for a memorial service at a future date.
