This was episode 99: Money Round wins 37 out of 99. This show has given out more trips than cash. And I know I'm captain obvious here, this is the 8th consecutive show the money round ends in failure.
Oscar is an ok player, but the reason he doesn't win the money round as often is that he blurts out the first word that comes to his mind then stops guessing, unless the player says another word. It's as if his words are limited too. Compare him with Melissa Peterman and Matt Iseman.
Because the clue "wine" will make them say "glass, chardonnay, red, white." But if they've spent 20 seconds guessing other names for pig and he says "chardonnay" and they say "wine," they'll remember "swine" which was on the tip of their tongue.
