An elderly neighbor of mine once struck up a conversation about his frail health—George’s doctor had warned him that his heart was bad. Suddenly he began to tell me about being a teenage lifeguard at a local pool during Prohibition. Every Friday afternoon a big car from Canada would pull up, and the driver would give him $5 to watch his car for him. $5 was a fabulous tip. Needless to say, this became a regular appointment.
A few years later George and his new wife were in Montréal. The city was jammed for a holiday, and they couldn’t find a hotel room. They were desperately quizzing a hotel clerk when someone in the crowd hailed him. It was the bootlegger whose car George had been minding by the pool a few years before.
They renewed auld acquaintance, and the bootlegger instructed the hotel clerk to give George and his wife a prize suite.
The anecdote seemed to be about life’s surprising coincidences. But a few years later I was talking to a retired carpenter. He began to describe being a doorman in New York City as a young man. In one of the apartments lived a gangster who was often visited in the evenings by members of his gang. They would send the doorman out on errands and would tip laviishly.
A month or so after our conversation the carpenter died. This let me know that he had told me about being an unofficial gangster because he was aware, as George had been, that his time was running out. The memories were haunting.
Both memories were especially meaningful as the storytellers summed up their lives. They had been unofficial outlaws, breaking out of the constraints of conventional culture. They had received privileged rewards for breaking the law, but the memories were important because the association with outlaws seemed important. You could say that both flirted with the idea of being a bigshot, or of being like an obliging son to a powerful and generous parent. After all, to a child, adults can do whatever they want. Everything has purpose. The child in us imagines grown-ups have perfect freedom.