Andrew Jackson's 1845 bequest of a gold box to the New Yorker "most valiant in defense of his country ad our country's rights excited and troubled New Yorkers and indeed many other Americans. Who was the bravest New Yorker? That question proved difficult, if not impossible, to answer, and neither New York City nor the eventual recipient escaped with reputations intact. Indeed, the 1857 campaign to award the box roiled editors, politicos, soldiers, and civilians, underscoring valor's multi-faceted character. Politics ultimately trumped character to highlight the contested (and elusive) definition of what precisely constituted valor.