Filed from 11 published puzzles

SADSACK

Set to 9 different clues across 11 published puzzles, most often “Born loser” — The New York Times, Saturday, 24 January 2009.

7 letters

Every clue on record, most used first

  • Born loser2 times

    The New York Times — Saturday, 24 January 2009

  • Pathetically inept person2 times

    The New York Times — Monday, 8 February 1999

  • Perennial loseronce

    The New York Times — Tuesday, 16 September 2008

  • Oafonce

    The New York Times — Sunday, 20 January 2008

  • Bumbleronce

    The New York Times — Saturday, 29 November 2003

  • Blundereronce

    The New York Times — Sunday, 28 October 2001

  • Pathetic bumbleronce

    The New York Times — Monday, 4 September 2000

  • Inept persononce

    The New York Times — Sunday, 8 August 1999

  • Cartoon privateonce

    The New York Times — Wednesday, 2 November 1994

Other answers to these clues