I was reviewing your code. When you add the players to the list you could add a ghost player Lotto as the first. Then if the random was the Lotto it would announce no one one and add the lotto amount to the Lotto Bank account. Then next drawing you would pull lotto's bank account to get the new jackpot.

From what i read on the iconomy wiki is that the getAccount creates the account if one doesn't exist. but you could use the hasAccount to check to see if lotto already exists. If not, then create it and then use the setBalance since iconomy will auto set the balance with the default.

I know this is just an implementation Idea. I would love to help add but i'd have to review the code more so i could understand how it works all together.