Black Swan, I don't know where you found that $5 bet quote, but I remembered something similar from the short story, "Goodbye Watson" ("Erections"/"Tales Of Ordinary Madness"), in which he says, "If I ever taught a class in creative writing, one of my prerequisites would be that each student must attend a racetrack once a week and place at least a 2 dollar win wager on each race...".
Okay, next question:
Where was the poem, "The Crunch", first published?