After tiring of a life in politics he gambled his future on a lot of rare Madeira that he bought for a song (because demand was listless) and started his company.

FORBES: Why Madeira Is The Next Great Thing In Wine

Standing in the construction magnate's Mexico City home on Mar. 2, 1998, Lerma says, Perusquia admitted he had gambled Lerma's fortune away on shaky Canadian gold stocks and used false account statements to cover it up.

FORBES: Ay, caramba!

Levein gambled on playing without a striker as he went all out not to lose the Euro 2012 Group I qualifier.

BBC: Czech Republic 1-0 Scotland

If Ike gambled on the weather and lost, Overlord would be a catastrophe, and he would have wasted every single life lost that day and condemned the people of Europe to an even longer wait for their freedom, an even longer wait filled with suffering and murder.

FORBES: Lead Like It's D-Day