Most likely a late 19th-century portmanteau of simon (“dollar”), from simon (“sixpence coin”) (17th-century British slang, perhaps related to simony?), and Napoleon (“French gold coin worth 20 francs, bearing the image of Napoleon III”). Perhaps from New Orleans.
simoleon (plural simoleons)
- (US, slang) A dollar.
- That'll cost you five simoleons.
- about 1900, O. Henry, Hygeia at the Solito
- "T'ought I was lyin' about the money, did ye? Well, you can frisk me if you wanter. Dat's the last simoleon in the treasury. Who's goin' to pay?"
- 1909, The International Bookbinder - Volume 10, page 240:
- Another brother working in an Alabama city has not sent a cold simolean or any long green since January; he has ignored several letters, but at last a registered letter found him O.K. and working.
- 1912, Delta Chi Quarterly, volume 10, page 286:
- We gladly did so with the result that we got a menu worth a dollar and a half or two dollars for a single simolean. Can you beat that?
- 1983, Newsweek, volume 101, page 178:
- Abetted by market-wise agents and paperback publishers with an eye for the speedy simolean, these double-gaited gonzos are perpetrating a plague of best-selling takeoffs of innocent newspapers, defenseless magazines, helpless self-help books - even the Good Book itself.