The Clinton/Bob Dole Crossword
The date was the 5th November 1996: the day of the US presidential election. The two candidates were in a close contest and the result was not yet clear. Out of this, an amazing crossword was compiled in the New York Times. One clue read, 39. The headline of tomorrow's newspaper (!), with 43. across. This clue was either going to be Clinton Elected, or BobDole Elected, but the crossword was set up so that either clue would fit.
The relevant Down clues all had two different answers, either of which would fit.
From Left to Right we have:
39. Black Halloween Animal. (Cat or Bat)
40. French 101 Word. (Lui or Oui, i.e. words that you learn when you first start French)
41. Provider of support, for short. (IRA or Bra)
23. Sewing shop purchase. (Yarn or Yard)
27. Short writings. (Bits (as in on a computer) or Bios)
35. Trumpet. (Boast (to trumpet something) or Blast (what you do with a trumpet))
42. Much-debated political inits. (ERA or NRA)
I'd also like to point out the relevance of 17 across and 68 across. Prognostication and Mister President.