Chesterton had a varied career as a soldier, serving in the Spanish Peninsular War against Napoleon, in America during the War of 1812–14 against the United States, and in Venezuela as a captain and judge-advocate in a British brigade of volunteers with the forces of Simon Bolívar. He was living on half-pay and studying to become a clergyman when, in 1829, he was appointed governor of Coldbath or Cold Bath Fields prison, a ‘bridewell’ or house of correction, in London.