Gambling in Macau has been legal since the 1850s when the Portuguese government legalised the activity in the autonomous colony. Since then, Macau has become known worldwide as the "Gambling capital of the world". It is the only place in China where casino gambling is legal.

1. Harry Kakavas: Almost $1 Billion. The biggest loss on this list goes to Harry Kakavas, an Australian real estate agent who made a fortune selling properties on the Gold Coast. Unfortunately for Kakavas, the more success he found as a real estate agent, the more he lost betting at the casinos.