Snap Judgment: When to Trust Your Instincts, When to Ignore Them, and How to Avoid Making Big Mistakes with Your Money

16. Gambling Continued: Stories We Tell Ourselves

A man I will call Al “Dogs” is a luminary in certain Brooklyn old-school gambling circles. (“Dogs” comes from all the time he spent at the dog track.) Al’s claim to fame is his extraordinary win at the Kentucky Derby a few years ago. On a single $100 bet on a trifecta, he cleared a million dollars. His life changed. Al Dogs moved out to the “island” (Long Island) and is the first to buy drinks for friends. The Governor of New Jersey once invited him to open a race.

Al remains a very heavy gambler. He is constantly at the track, including his old weakness: the dog track in South Florida, a sociological low. Al doesn’t discuss his losses, only his wins. And over the years, the losses may have been ...