Clark Smiley liked to win.
Why shouldn't you let a 16-year old use a handheld Dell computer to keep score during a chess match? Because chess software can beat human opponents, that's why, and sometimes the urge to win by cheating is just too strong.
Read the article: Rooked. The supremely old-school game of chess is dealing with a very avant-garde brand of unsportsmanlike conduct, Grantland>>
(Thanks to Andrew Scott for the find.)