Shoe Money Tonight

Through the Handsome Jackpot DLC you'll encounter some fancy chests with a robotic voice as you approach.  To open them, 'cards' are drawn onto the front, keep drawing to get close to a total of 21 (king/queen/jack = 10).

If you go bust (exceed 21) you'll get nothing special from the chest.

Make sure to open every chest you find and this should pop sooner or later.  Some chests are in the VIP areas which you'll need to pay to enter.

If you miss them, you can revisit again later to try again.