Filed from 4 published puzzles

HOPER

Set to 3 different clues across 4 published puzzles, most often “Optimist” — The New York Times, Sunday, 8 September 1996.

5 letters

Every clue on record, most used first

Optimist2 times
The New York Times — Sunday, 8 September 1996
One with fingers crossedonce
The New York Times — Tuesday, 17 July 2007
Wishful oneonce
The New York Times — Tuesday, 8 February 2005

Other answers to these clues

ALADDIN7 letters