I have won $25,000 twice. Once on a $100 slot machine, once in a casino drawing.
The most I have won on a single bet on a casino table game is $12,500 (500 to 1 on a $25 bet).
The most I have won on a lottery drawing is $500, The most I have won on a single ticket is $450.
You should, however, understand that I gamble enough that I lose thousands of dollars in a typical year.