This chapter examines British radical attitudes towards America during the 1790s by taking up the case of William Winterbotham, a Plymouth Baptist preacher who was jailed in Newgate prison for four years (1793–1797) for allegedly seditious content in two sermons he preached in November 1792. Winterbotham's most ambitious work was An Historical, Geographical, Commercial, and Philosophical View of the American United States, published in four volumes in 1795. It demonstrates the fascination that America held for British radicals beyond Thomas Paine, Joseph Priestley and Richard Price. Among his many concerns, Winterbotham was highly critical of the institution of chattel slavery. The chapter explores Winterbotham's political analysis of the new republic and shows that his imprisonment for seditious libel was bracketed by contemporaries with the more conspicuous 'martyrdom' of five men sentenced to transportation by the Scottish High Court of Justiciary.