When panhandling in Bakersfield, California, an Arthur J. Hayden received 25 cents ($4.70 today), which he took to a casino and parlayed into $690 ($13,000 today). The next day he grew his winnings to $1,000 ($19,000 today), which he put in a postal savings account.
When he went back to begging on the street, he was arrested and convicted. For punishment, rather than pay a fine and have to dip into his winnings, he chose to serve 90 days in jail.
Photo from Smithsonian National Postal Museum