Walter L. Kennedy graduated from Chelsea High School and began his career at Pratt & Whitney. He served in the United States Army Air Forces during World War II, reaching the rank of Corporal. Post-war, Kennedy managed the Chelsea Co-Op Grocery and worked for American Home Foods before entering the automotive business. He spent over two decades in the Vermont House of Representatives, including a period as Speaker. Kennedy also ran for governor and chaired the Vermont Republican Party.

Walter L. Kennedy's political career reveals a deeply rooted commitment to local interests, underscored by his long tenure in the Vermont House of Representatives and his role as Speaker. His business background in retail and car dealing suggests an ideological affinity for market-driven solutions, yet his legislative actions hint at an unexpected alignment with progressive environmental policies. Kennedy's rhetorical style appears to blend traditional conservative values with a pragmatic flexibility that appeals across party lines. This juxtaposition makes his political identity both intriguing and complex, inviting further exploration into how he reconciles these seemingly disparate elements.