His 1996 memoir, Confessions of An Ivy League Bookie, details his plight as a 33-year-old struggling freelance writer who enters the numbers-running business in New York.
The book tells how a friend and Brown University alumnus working as a bookie introduced him to the illegal profession.
According to Alson, “everything in the book is completely honest.”
For nearly six months, he took illegal bets on baseball, basketball and football games, working alongside not only people dubbed “Spanky” and “Monkey,” but, he says, also Brown and Dartmouth graduates.
Eventually, a police sting broke up the operation and Alson says he was arrested and spent 36 hours in jail.
In the end, his stint as a bookie netted him a total of $8,000.
“Pretty pathetic, huh?” he quips. “I had such a fear of getting sucked into that world, and I knew that if I made a lot of money, I would get sucked in.”
No Born Criminal
Though Alson briefly sought a career in crime, he is a writer at heart.
He is the nephew of famous novelist Norman Mailer ’43 and he said his uncle had a large impact on him.
“I wanted nothing more than to be like him. That’s a difficult goal to set for oneself,” Alson says. “He has been incredibly supportive of me. We maintain a very close relationship.”
Alson began writing “really bad poetry” when he was about 18 years old, and he says that becoming a writer was like “joining the family business.”
He says his father was a playright, and his mother had also tried her hand at writing.