Caleb P. Bennett spent his early years in Chester County, Pennsylvania, before relocating to Wilmington. He served as a lieutenant in the Continental Army during the American Revolutionary War, participating in several key battles and being wounded multiple times. Post-war, Bennett held various military positions, including commanding artillery during the War of 1812. He was elected governor of Delaware in 1832, focusing on penal system reform and advocating for internal improvements such as breakwaters and railroad upgrades. Bennett's tenure was marked by his strong stance against states' rights nullification of federal tariffs.

Caleb P. Bennett's political identity is marked by a surprising blend of progressive penal reform and staunch federal authority. Bennett's advocacy for abolishing imprisonment for debt and the pillory reveals a progressive streak, yet his vehement opposition to South Carolina's nullification of a federal tariff showcases an unexpected allegiance to federal strength. This ideological juxtaposition hints at a highly calculated approach to balancing reform with maintaining national unity.