This idiom describes coming very near to success but ultimately failing, as if almost winning a cigar prize at a carnival but falling short. It conveys near-misses, often used in competitive, professional, or personal contexts to highlight effort without reward. The phrase carries a tone of disappointment, encouragement, or teasing, reflecting cultural values of perseverance and the human tendency to fall just short. Its carnival imagery evokes a tantalizing miss, resonating in scenarios like contests or deals. The idiom softens failure, making it a lighthearted metaphor for close calls.

The phrase originated in late 19th-century America, tied to carnival games where cigars were prizes, as noted in fairground records. Its earliest recorded use appears in *The New York Times* (1920s), describing a near-win in sports. The idiom gained traction in the 1930s, amplified by radio and film, notably in *Annie Oakley* (1935). Its adoption, primarily in the U.S., stems from its nostalgic imagery and applicability to near-success, with some use in Canada and the U.K.