William Marion Bennett

William "Bill" Marion Bennett, 82, lovingly called "Pop" by his grandchildren and remembered for his stories, wit, and generosity, died on November 26, 2025, in Smyrna, Georgia. His humor and his gift for turning strangers into friends shaped the lives of family, friends, and colleagues alike.
Born in Baltimore, Maryland, to William Marion and Aster Westbrook Bennett, Bill spent his childhood roaming creeks, fishing, and discovering early the joy of music and cars. When his family moved to Alabama, he attended Phillips High School in Birmingham, where he played trumpet in the marching band. He treasured that trumpet for the rest of his life and proudly kept both it and his high school letterman jacket as symbols of a time that shaped his love of music. His fascination with cars deepened during these years as well. His first car was a Studebaker. He even raced cars, and over the decades he was just as comfortable behind the wheel of a camper as he was in a Porsche.
Bill attended the University of Alabama, where his devotion to Crimson Tide football took root and never loosened its grip. He followed the Tide with a kind of reverence, memorizing seasons, and treating each kickoff as if it couldn't be missed. His admiration for Coach Paul "Bear" Bryant bordered on the sacred. "Roll Tide" wasn't just a cheer, but part of Bill's vocabulary and his joy.
Bill cherished his years in Tifton and Woodstock, Georgia; Clearwater, Florida; at his Lake Murray home in Columbia, South Carolina; and at his beloved cabins in North Georgia. Each place represented a chapter marked by music, food, and the people he gathered along the way. He loved exploring new restaurants and returning to old favorites, and he could tell you the three best places to eat in nearly any town in the country.
Bill loved music and food festivals, and any gathering where people came together simply to enjoy life. He had a deep appreciation for art and became an avid collector. Whether it was fine art, regional artists, or pieces discovered in small galleries during his travels, Bill valued anything that told a story. He approached food the same way: with enthusiasm and reverence. He relished a good meal, whether at a white-tablecloth restaurant or a roadside barbecue, and enjoyed everything from a margarita to a simple Arnold Palmer, which he ordered with such conviction that it routinely confused young servers. His love of food, music, travel, and art made for many lasting memories.
He became famous, sometimes even infamous, as "Willie the Clown" in Shriner parades, spreading joy to children and adults alike. He taught newcomers how to apply clown makeup, twist balloon animals, and embrace the art of making others smile. Bill volunteered with the Shriners Hospital for many years, served on the board of Richland Memorial Children's Hospital, and held significant leadership roles in the Boy Scouts, where he received the Silver Beaver Award for his extraordinary service to youth. His civic contributions were countless.
But it was in the world of self-insurance and employee benefits that Bill left his most indelible public mark. A visionary, Bill helped companies understand and adopt the self-funding model, reshaping how employers provided health benefits. Throughout his career, Bill founded, led, or helped shape organizations including WORKsiteRx, Healthcare Solutions Group, AU Resource Group, Alliance Underwriters, Vasa Brougher, First Southwest Risk Management, and Colonial Life. He also served in leadership roles at Reliance Standard Life, Hartford Life, Continental National American, and several MGUs. His commitment to learning continued through advanced programs at Penn State University, the College for Financial Planning, the Employers Council on Flexible Compensation, and the Society of Certified Senior Advisors.
His leadership extended far beyond his own companies. He served as Chairman and President of the Self-Insurance Institute of America (SIIA), contributed to numerous national boards, and became a respected national educator and advocate. He appeared on CNN, Fox News, CBS News, WGN Chicago, and NPR, and was chosen as a delegate to Mainland China to consult with the Chinese Ministry of Labor on employer-based benefits.
Bill possessed a leadership style that was entirely his own. When he stood at the podium, people listened. A blend of strategic clarity, irrepressible humor, and an instinct for turning difficult conversations into productive ones. He had a gift for threading sharp insight through a well-timed one-liner, transforming tension into possibility and redirecting negativity with grace. His humor never distracted from his message; it illuminated it. His colleagues often described him as the consummate "Class Act," a leader who balanced warmth with rigor. Early in his career, he became known for challenging people in ways that made them better, setting high expectations while making them feel at home. Many who worked with him or across the table from him would go on to consider him not just a mentor, but a lifelong friend. His relationships often stretched across decades, built on respect, candor, and the genuine care he extended to those around him.
Yet Bill's legacy is equally rooted in humor, warmth, and storytelling. His "Bill-isms" were legendary:
"She talks so much you'd think she was born with a phonograph needle in her mouth."
"He was madder than a mosquito in a mannequin warehouse."
"I'd just as soon wrestle a circle saw."
"I could eat the tail off a ragdoll."
"His rendition of Rindercellar and Her Three Sad Blisters, his own twist on Cinderella, was unforgettable, and whenever Alabama made a questionable play, you could count on hearing his whispered, perfectly timed 'Mother Goose.'"
Above all, Bill loved people. He cherished the southern traditions he was raised in, the Bama nation that shaped his Saturdays, the friendships that became lifelong bonds, and the family who brought him the greatest joy.
Bill is preceded in death by his parents, William Marion and Aster Westbrook Bennett, and by his daughter, Portia Loraine Bennett. He is survived by his devoted wife, Yvonne Owens Bennett; his sister, Begie Bennett Willis; his dog Max, and his children and their families: Desiree Bennett LaRoche and her husband, Sam, and her daughter, Willow Gruber; Shannon Barnes Hipp and her husband, William, and their sons, Henry and Jack; Carrie Barnes Conley and her husband, Rodney, and their children, Crosby and Stella; and Aaron Bennett and his wife, Hannah, and their daughters, Naomi and Rosie.
Bill Bennett leaves behind a world made brighter by his leadership, his generosity, his love of music, his stories, and his unparalleled ability to transform any moment with wisdom, warmth, and a perfectly timed one-liner.
A Celebration of Life will be held on Thursday, December 11th at 2:00 PM at the Carmichael Funeral Home Family Celebration Center in Smyrna, Georgia. Friends and family are warmly invited to gather in Bill's honor and share in a few of his favorite joys-good barbecue, heartfelt memories, and plenty of storytelling.
In lieu of flowers, please consider supporting a charity that reflects Bill's love for his grandchildren and the things he cherished most-music, education, the arts, or a community organization of your choice. And most of all, honor him by sharing a story, a meal, or a laugh with someone you love.