CONTENDER
Set to 2 different clues across 2 published puzzles, most often “Prison guard?” — The New York Times, Tuesday, 14 March 2006.
9 letters
Every clue on record, most used first
- Prison guard?once
The New York Times — Tuesday, 14 March 2006
- Money in prison?once
The New York Times — Tuesday, 17 December 2002