When you go back to the casino and play CalicoJack again, you'll notice that the outcomes are the same.Once you record all the possible patterns of winning and losing, restart and play the game again.You'll notice that sometimes you can actually win them more than twice in a row if you're very lucky.
As you play, record every single winning and losing outcome of the game as much as you want.Play the low stakes CalicoJack table casually.Get to the casino and buy some Qi coins (at least around 1,000 Qi).Make sure that your day is a very lucky day as it means there's a high frequency of winning more than two or three times in a row.
Calico Jack have the same pattern of winning and losing when you restart the game and play it again on the same day.