David D’Alessandro rose from humble roots in upstate New York to become one of Boston’s most respected business leaders. His flair for business battle is highlighted in his three bestselling books: "Brand Warfare," "Career Warfare" and "Executive Warfare."
In Greater Boston’s 1 Guest series, the former CEO of John Hancock Financial Services opened up to host Emily Rooney about growing up in Utica, his father’s gambling addiction and run-in with the mob and his early work history.
Childhood in Utica
D’Alessandro was born in Utica, New York. East Utica, to be precise.
“When you’re from Utica, you have to be distinctive about where you’re from,” he said. “Kind of like when you’re from New York, you’re from Brooklyn, not the Bronx.”
From an early age, D’Alessandro said, he had an aversion to authority figures. His own mother was no exception. “My mom told me I couldn’t go fishing. I was 4 or 5 years old,” he said. Undeterred by his mother’s orders, he constructed a fishing line out with a piece of string and a nail and proceeded to fish from the family goldfish bowl. Unfortunately for him, the goldfish just weren’t biting.
“Perhaps because the nail was bigger than the fish. And there was no bait on it,” he said.
D’Alessandro moved on to Plan B and scooped the fish out with a large pasta spoon then left them on the kitchen counter. His mother noticed them immediately when she came home.
“It didn’t work out so well,” said D’Alessandro. “I had them for dinner.”
Gambling
D’Alessandro said his father was the smartest person in the family, boasting an IQ of 165 and speaking five languages, including Japanese. Unfortunately, he also struggled with compulsive gambling, a habit that “put the family through hell.”
“He was addicted to horses,” said D’Alessandro about his father. “He played every day. Every day, including the day he died.”
His father’s gambling habits also got him into trouble with some of the neighborhood’s more notorious characters. As a child, D’Alessandro remembers witnessing a terrifying encounter between his father and a group of gangsters at the family’s grocery store.
“Some henchmen came in and we had a big chopping block,” said D’Alessandro. “They made my dad put his hand down and they kept plunging a knife between his fingers because he owed a few hundred dollars.”
On casinos in Massachusetts
Given his own family’s troubled history with gambling, it’s not surprising that D’Alessandro was disappointed by the recent legalization of casino gambling in Massachusetts.
“Gambling is an addiction,” said D’Alessandro. “For the legislature to push so hard for casino gambling knowing they are going to addict people … it’s anathema to me because I thought the state knew better.”
He added, dryly, “Why don’t we just open up crack cocaine parlors and take the tax off of that?”
Early jobs
It’s hard to believe one of Boston’s most respected businessmen was ever fired from a job. But D’Alessandro admitted his first job at a movie theater was not his biggest success.
“I got fired because the owner of the theater insisted I walk around with a flashlight … telling people to stop cuddling and making out with each other,” he said. “I didn't think it was good for my physical health in an Italian American neighborhood to be breaking up young people from cuddling.”
