Bennett, 62, graduated from Danvers High in 1967. Born in Duxbury and the oldest of seven children, Bennett moved to town when he was a freshman in high school.
Bennett said his family was active politically going back generations. His father, E. Howard Bennett, had started the “Observer” newspaper in Marblehead in the 1950s, Bennett said.
His paternal grandfather, Frank P. Bennett, also worked in publishing. Bennett’s great great grandfather served as a state representative from Everett and Saugus for a total of five terms.
On his mother’s side, his grandfather was a strong influence.
“My grandfather is the person I most admire in life,” Bennett said of his maternal grandfather, James Jenner. “He just instilled in me a work ethic. He sold feed to the local farms throughout New England. This was a farming area years ago. Summers I spent traveling with him making calls to his customers.”
Jenner also served 13 years as a selectman and assessor in Duxbury.
Bennett credits both grandfathers for his work ethic.
“A good leader leads by example,” Bennett said. “It’s not do as I say, it’s do as I do.”
Bennett’s family eventually moved to the North Shore to be closer to the area’s farming community. His mother remarried — Bennett’s father died of a heart attack at age 33, when Bennett was 11 — and moved to Marblehead. Bennett spent a few years there before moving to Danvers.
After graduating Danvers High, Bennett attended Boston University for two years in the late 1960s, then left college to work. He worked for Almy’s department stores for 15 years, becoming an assistant buyer and then a buyer. He spent another 13 years with Rich’s department stores.
“I was there until 1996 when they called us in and said: ‘We are closing the doors,’” Bennett said.