Abstract: A method of playing Blackjack is disclosed wherein the player can wager that his hand will be broken by placing a side bet which is referred to as “Hit Insurance”. Two aspects of the invention are disclosed. The first aspect allows the player to place the side bet after he has seen his initial hand. If the player has 12 through 16 and the dealer has seven through ace as the upcard, the player is given the option of placing the side bet that he will be broken when he receives the hit card. In a first variation, the player places a side bet against a single hit and can renew the bet if he loses on the hit. In a second variation, the player places a side bet against multiple hits. In a second aspect of the invention, the player places a side bet before he is dealt any cards. In a first variation, the side bet loses if the dealer has 2 through 6 as the face card. In a second variation, the side bet pushes if the dealer has 2 through 6 as the up card.