Cleave Simpson graduated from Alamosa High School and the Colorado School of Mines, establishing a solid educational foundation. He spent several years managing institutional risk in high-finance before returning to the San Luis Valley to oversee his family's farming and ranching operations. Simpson has held leadership roles in both the public and private sectors, including serving on the Adams State University Board of Trustees and managing the Rio Grande Water Conservation District. His extensive experience in agriculture, water conservation, and public service positions him as a knowledgeable and experienced leader.

Cleave Simpson's political identity is shaped by a unique blend of deep-rooted localism and an ideologically agile approach to policymaking. His tenure in the Rio Grande Water Conservation District and his family's farming legacy underscore a commitment to regional interests, yet his legislative actions often reveal unexpected alliances with opposing factions. Simpson's rhetorical style emphasizes collaborative leadership, but his policy decisions suggest a strategic balancing act between traditional rural values and modern environmental stewardship. This tension invites further inquiry into how he reconciles these seemingly divergent priorities.