Southbury- Robert “Bob” Holley, 92, of Southbury, passed away unexpectedly on August 4, 2026, after a brief illness.

Bob was born on February 5, 1934, in Hartford, Connecticut. After graduating from Hartford High, he joined the U.S. Army and was stationed in Japan. Upon completing his tour of duty, Bob attended and graduated from the University of Connecticut, where he met the love of his life, Elaine Bilsky.

Bob and Elaine were married for 65 years, living in Southbury, CT for nearly all that time. They had three children, Lynn, Robert, Jr. (“Rob”) and Glenn, and six grandchildren: Cate, Julia, Jack, Rachel, Max and Sam. Bob, or “Doo” as he was known to family, was an incredibly sweet, kind and devoted husband, father and grandfather. Bob’s family was his greatest joy, and he relished time together in Southbury, or Venice, Florida, Cape Cod, Swanzey Lake or various points in between.

A C.P.A. by training, Bob started his career in accounting before moving to the car business. He opened his own dealership, Holley Chrysler Dodge in Middletown, Connecticut, which he ran for nearly 20 years.

Bob was an avid and long-suffering fan of the Boston Red Sox and the UConn Huskies men’s and women’s basketball teams until their changed fortunes in recent decades rewarded his loyalty with unprecedented success. Always community-minded, Bob volunteered his time to various youth sports, church and civic activities and organizations. In later years, he was active in various Heritage Village leadership roles. He enjoyed golfing, gardening, poker, pizza and ice cream. Bob was a fierce competitor at RumiCube, which he usually won.

Bob is survived by his beloved wife and best friend Elaine, his sister Joann Celentano of Rocky Hill, CT, his children Lynn Holley and her husband Chris McCaffrey of Ridgefield, CT, Rob Holley and his wife Christina or Sterling, VA, and Glenn Holley and his wife Rebecca of Hebron, CT, as well as by his cherished grandchildren Cate and Julia McCaffrey, Jack and Max McAdams, and Rachel and Sam Holley.

Services will be held privately. To leave an online condolence, please visit munsonloveterefuneralhome.com.