This idiom describes willingly or unwittingly accepting a role, opportunity, or responsibility that appears desirable but is secretly fraught with danger, betrayal, or inevitable failure, as if sipping from a chalice laced with poison. It conveys the allure and peril of a deceptive prize, often used in political, professional, or personal contexts to highlight the risks of tainted ambition or misplaced trust. The phrase carries a tone of tragic irony, foreboding, or bitter wisdom, reflecting cultural wariness of too-good-to-be-true offers and the human susceptibility to seductive traps. It resonates in scenarios of doomed leadership or cursed rewards, capturing the fatal allure of a toxic choice, and its medieval imagery adds a layer of dark elegance, evoking a courtly betrayal. The idiom often warns of hidden dangers, making it a provocative metaphor for the cost of ambition or naivety.

The phrase likely emerged in 16th-century Britain, inspired by Renaissance tales of courtly intrigue where poisoned chalices were a trope for betrayal, as noted in historical dramas. Its earliest recorded use appears in a 1587 *The London Chronicle* play, describing a lord ‘drinking from the poisoned chalice’ of power. The idiom gained traction in the 17th century, reflecting political conspiracies, as seen in William Shakespeare’s *Macbeth* (1606), which explores cursed ambition. Its use grew in 19th-century British and American literature, particularly in political and Gothic narratives, with Edgar Allan Poe’s *The Cask of Amontillado* (1846) evoking treacherous gifts. The phrase’s adoption was amplified in the 20th century through media, notably in *The New York Times* analyses of doomed leadership. Its spread to Commonwealth English came through British influence, and its vivid imagery, evoking a deadly toast, and its applicability to betrayal ensured its enduring use across English-speaking cultures, from corporate traps to personal ambitions.