John “Jack” Rowlandson Clegg Jr., 95, passed away peacefully with his family by his side on August 19, 2026.
John was born in West Hartford, Connecticut on June 22nd, 1931. He was always hands-on and began helping with his family’s florist business at a young age. His natural ability was evident even in the first grade, when his teacher had him build a chair in class back in the 1930s. After graduating from high school, he joined the United States Air Force and later earned his bachelor’s degree in business from the University of Connecticut.
In 1955, he married his wife, Audrey, with whom he shared 63 wonderful years. Soon after their marriage, they moved to Pennsylvania, where Jack began his career as an insurance broker. After working in Philadelphia and Erie, he moved to the Pittsburgh area and continued his career with Alexander & Alexander/Aon.
John loved life and was a dedicated, hardworking man. He often took his family on weekend getaways in their camper, creating many cherished memories together. Following retirement, he and Audrey enjoyed many years of traveling and eventually became snowbirds, spending the winter months in Leesburg, Florida. While there, he joined a woodcarving club at the park where they stayed and created many beautiful pieces, including handcrafted walking sticks.
He was known as a good and kind man who always kept busy. He put his family first and faithfully cared for them throughout his life. He treasured his memories of growing up and could recount those stories in remarkable detail. He was a Freemason for more than 50 years and a proud member of the National Wood Carvers Association.
A true “Jack of all trades,” he loved working around the house and trying new things. He remained active by reading, carving, birdwatching, gardening, taking road trips, and hiking with his dogs until the final few months of his life. He was admired by many and will be deeply missed.
He is survived by his daughters, Susan Clegg Boswell and Elissa Clegg, his granddaughter, Brianna Clegg, his sister, Joyce Logan and his two beloved doxies, Chipper and Rusty.
In addition to his parents, he was preceded in death by his wife, Audrey Clegg, his son, Randall Clegg, his granddaughter, Trista Clegg-Orienza, his brother, Phillip Clegg and many other beloved family members, friends, coworkers, and pets.
The family would like to express its heartfelt appreciation to Pinnacle Hospice of Pittsburgh, Pennsylvania, and Ancora Hospice of Rockingham County, North Carolina, for the compassionate care given to Jack and his family.
