In highschool we used to gamble for quarters in between classes and after school. Our favorite game was in between. The dealer gave everyone two cards and there is a pot with everyone's bets in the middle. We started off with one quarter from each player. Before the third card is dealt to the player, the player had to announce his bet, as low as a quarter or as high as the pot. If the third card dealt to him was in between the first two cards then he wins whatever he bet(ex. If he had a 2 and a 10 and the third card was a 3, then he wins. If the third card was a 2 and a 10 or lower or higher then he loses. If the first 2 cards where the same, then the player must bet whether the third card is higher or lower)
At one point there was about eight of us playing and the pot grew to about $150 and we were just betting quarters. But since a couple of people bet the whole pot and lost, the jackpot grew quickly. So my turn to bet came up and everyone was tense at this point since they really wanted me to bet the whole jackpot and lose. My cards were 4 and a Jack. So I really had to think if the chances of getting a card in between those were high enough to risk my paycheck that I recently received from my part time job. I made my bet and told the dealer to bet the whole jackpot and I had to show my check to prove that I could cover it if I lost. And the guys laughed and was sure I wouldn't win it. The dealer slowly flipped up the third card to me and a 5 came up.
That was the biggest gambling win I ever had. To this day the most that I gamble is $3 on a lottery once in a while.