Would winning $50,000 help out your family? Ya it would mine too! Enter with American Family for the chance to win $50,000 cash! If I won, I would probably pay off a lot of bills, but I would definitely squeeze a vacation in there too! To enter, just fill in your contact information. Be sure to get you entry in soon, this sweepstakes closes December 31st! What would you do with $50,000?