Chauncey Cleveland was admitted to the bar in 1819 and began practicing law in Hampton. He held various roles in the Connecticut House of Representatives and served as state's attorney and state bank commissioner. Cleveland transitioned from the Democratic to the Republican Party and was elected governor of Connecticut in 1842-1843. He also served in the U.S. Congress and participated in the Peace Congress of 1861, demonstrating a commitment to national unity and legislative governance.

Chauncey Cleveland's political journey reveals an ideologically agile approach, transitioning from Democratic to Republican affiliations as he sought to navigate the evolving political landscape. His robust support for the government during the Civil War, coupled with his role in the Peace Congress of 1861, highlights a complex stance on conflict and unity. Cleveland's advocacy for industrial growth and protective tariffs, typical of the Republican Party, suggests a calculated alignment with economic policies that benefit regional industrial interests. This blend of strategic party switching and steadfast support for certain economic policies indicates a politician deeply attuned to the shifting tides of national and regional interests.