• Image about Sankaty Head Golf Club
Photography by Jensen Larson

For the privilege of hard work six days a week, a morning and an evening roll call, and curfew, the caddies are charged a nominal amount for room and board.

They are allowed to keep all the money they make from caddying (a per-bag amount that’s consistent with caddy fees at similar clubs in New England, plus generous tips from the members and guests), which is deposited into their bank account each day — the first lesson in money management for many caddies. Most caddies will make enough to save a nice amount by summer’s end, almost all pure profit. If finances are an issue for any caddy, the room and board charge is returned at the end of the summer.

“They experience the same memories and the same experiences as caddies from years ago,” Montesano says. “It’s a camp where you earn money, learn values to respect ?others and yourself and to take responsibility for your actions.” His story is typical of many kids when he first came to the camp in 1969: He came simply because his parents wanted him to — they thought it was a good summer activity.

“After one day I was ready to come home — but I learned in the seven years I was here. And I was able to take what I learned to the corporate world with me,” Montesano says. But after a stint in the corporate world with Frito-Lay, he felt the call to return to Sankaty, and he became the full-time director in 2007. “Every camper thinks about the camp when he goes out into the world.”

Donovan first heard about the caddy camp from his older brother John, who caddied here from 1997 to 2000. Matt caddied from 1998 to 1999. And like most Sankaty kids, he was unsure what he wanted to do with his life — but he was up for a summer adventure. “All I knew was that I wanted to work in sports. I was just playing golf and going to school,” he says.

While he had caddied before in Boston, where his dad ran an unrelated caddy foundation, he found the experience at Sankaty was unlike any he had ever seen. A typical day for Donovan included waiting at the caddy area, termed The Bench in caddy lingo, and having corporate tycoons like Bill Gates and Warren Buffett casually stroll up and ask if he was available for a loop. Donovan also met current NBA player Mike Dunleavy Jr., along with dozens of businessmen.

“It’s such an unassuming club. Everything you see in Caddyshack about how they treat caddies poorly didn’t happen there. The members treated us great,” he says.