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Looking over the eoection room on a typical Sunday during football season, he can only dream what it would look like gambling on the election Election Day. Long, like many people who bet in prediction markets, is no political expert. Every great event leads to speculation in numbers. This Is How You Gamble on the US Presidential Election. Gambling on papal elections. Think Carly Fiorina did really well in that last debate?By Rob Shaw. VICTORIA – British Columbians looking to bet on Tuesday’s U.S. presidential election are wagering Republican candidate Donald Trump could make them some serious money. More than $. Miles Markstein, a year old bartender in New Orleans, is also wagering on the Republican primary. He says he made almost $1, in the and elections, and his reasons for doing it were simple: "I was able to predict things pretty well politically, I love gambling, and, you know. Gambling on papal elections has at least a year history. Betting on 16th-century papal conclaves are among the first documented examples of gambling on election outcomes. During the same period, gambling was also common on the outcomes of secular Italian elections.