Never mind the slings and arrows of outrageous fortune, here at InsideEdge we're more interested in the fortunes made from outrageous gambles. The past is littered with the forgotten stories of bookies, politicians, card-sharps, money men, crooks, inventors, singers, businessmen and soldiers who took incredible gambles that never paid off. But history is written by, for and mostly about the winners.

So we asked all of InsideEdge's many contributors to trawl the centuries for history's most extravagantly clever, most disgustingly daring, most downright lucky punts to have offended gambling decency, and sifted through hundreds to produce our top 25.