I just posted a story about playing a hustler on Rittenhouse Square (http://www.chess.com/article/view/my-game-against-the-hustler) but that reminded me of a story my college coach, Donald Byrne, told me. Since I consider it an obligation to not let Donald's fun stories die, here it is:
In the 1940's Donald was 13 and his brother Robert (later a GM) 15. The dress code for Central Park tennis was "tennis whites" and the two teens dressed accordingly for their fun tennis match.
After tennis they happened to pass an area where a park hustler was playing chess. Donald said the hustlers there tended to be in the 2200-2300 range.
Older brother Robert approached the hustler and asked how much he was playing for. The answer was 25 cents per game (maybe $5 in today's money). Robert said sure, and sat down to play. They played three games, each of which Robert won easily.
The boys pocketed their 75 cents, said thanks, and left, leaving the poor hustler to wonder what was happening now that he was losing to 15 year olds coming off the tennis courts (i.e., Who was that masked man?)
As with all of Coach Byrne's stories, he laughed heartily when telling it and we (the eager audience of chess club players) could never help but laugh along, too.
For those of you whose only acquaintance with Donald is that he lost the Game of the Century to Bobby Fischer in 1956, Donald was a super-strong player, many times representing the US in the Chess Olympiad. After he won the US Open in 1953 (http://en.wikipedia.org/wiki/U.S._Open_Chess_Championship) I believe at that point he was the second rated player in the US behind Sammy Reshevsky. Donald Byrne is a member of the US Chess Hall of Fame.