sharpie

Etymology

From sharp + -ie (“diminutive suffix”).

noun

1. (colloquial) An alert person.
   Eunice Marshall asked in a bored tone, "Are you, by any chance, selling magazines?" Daisy grinned childishly, enjoying Eunice's mistake. "You're quite a sharpie, aren't you, ma'am? You figured me out a whole lot faster than most people do." 1988, D. Miller Morgan, A Lovely Night to Kill, page 64
   You have to beat a lot of real sharpies, guys who have been playing for years. 2012, Richard W. Munchkin, Gambling Wizards, page 109
2. (US, regional) A knowledgeable fisherman.
   1976 December, Ken Schultz, Field & Stream Fishing Contest Winners: Nothing but the Best, Field & Stream, page 78, Eventually DeBlasio became a sharpie. In New York and New Jersey coastal fishing parlance a “sharpie” is one who fishes seven days a week all summer long, selling his fish to the market to make a living. Sharpies supposedly have fishing down to a science, to such a degree that they only go to particular places, at particular times, using particular fishing methods, and come back with a boatload of fish while everyone else wonders in amazement.
3. (US) A swindler.
   Three booths down a couple of sharpies were selling each other pieces of Twentieth Century Fox, using double arm gestures instead of money. 1953, Raymond Chandler, The Long Goodbye, Penguin, published 2010, page 102
4. (US) A long, narrow fishing boat used in shallow waters.
   He brought this pair of sharpies, the Lucia and the Ella, to Beaufort by schooner and began to use them for fishing, oyster dredging, and even as a passenger ferry and party boat. The sharpie is a flat-bottomed, shallow-draft vessel of moderate size, comparable to a sloop or schooner. 1995, Rodney Barfield, Seasoned by Salt: A Historical Album of the Outer Banks, page 168
   On the other end of the spectrum are the flat-bottomed sharpies. The earliest sharpies were developed in the mid-nineteenth century as the ideal boats for the oyster fishery of the Connecticut shore. 2006, Greg Rössel, The Boatbuilder's Apprentice, page 293
5. (birdwatching) Clipping of sharp-shinned hawk.
   It is harder to gauge the shorter tail of sharpies, but on sitting birds the tail shape is a more useful character than it is on flying birds. Sharpies of all ages and sexes almost always show a notched tail when they are sitting. 2005, Bill Thompson, Eirik A. T. Blom, Jeffrey A. Gordon, Identify Yourself: The 50 Most Common Birding Identification Challenges, page 93
   My mother had lost a considerable number of spring chicks to a raiding sharpie. 2010, Era S. VanDenburg, The Natural World of Ivy Lane, page 48
6. (Australia) A member of a violent, fashionably dressed youth gang of the 1960s and 1970s.
   The Circle Ballroom in High Street Preston was another popular sharpie hang-out.[…]Sharpies were all deep drinkers. 2006, Iain McIntyre, Tomorrow Is Today: Australia in the Psychedelic Era, 1966-1970, page 47
7. A Sharpie or other brand of felt-tipped marker pen.