On 18 August 1800, the satirist John Wolcot (aka Peter Pindar) entered a London bookshop and assaulted a fellow satirist, William Gifford, with a cane. This essay examines their feud within the contexts of Romantic-era notions of chivalric masculinity and the class symbolism of caning. Both middle-class writers felt entitled to deploy chivalric rhetoric and physical violence and insisted that they were honorably defending their reputations. But they grossly miscalculated how their hyperaggressive behavior and emasculatory rhetoric would be received during a time in which the code of gentlemanliness was evolving. Although Gifford’s adherents pronounced him the victor of the battle of the bards, neither satirist performed chivalric masculinity convincingly, and their mutual character assassination campaigns undercut their claims to gentlemanly status. The British print media’s responses to the Wolcot—Gifford caning affair provide insights into the inchoate embourgeoisement and shifting conceptions of chivalric masculinity during the Romantic period.