They say you need to play to win and many have tried all across Central New York. The most I've scored playing the Powerball was $20, but at least it was more than I invested. Saturday's jackpot is estimated at $856 million with a cash value of $372 million. READ MORE: Spend A Night in Derek Jeters Former MansionSo, are you feeling lucky? Deagreez DeagreezLuck of the DrawOver the years there have been many big money winners right in our own backyard.