scorecardresearch Skip to main content

He won the lottery twice in four months — so why does he still live in a trailer?

Robert “Bobby” Stuart was photographed in front of his home in Kennebunkport, Maine, on Sept. 13.Yoon S. Byun for the Boston Globe

KENNEBUNKPORT, Maine — Bobby Stuart is a simple man.

He’s lived in the same weathered trailer for more than 40 years. He makes his living operating a front-end loader. Every night after work, he stops in for supper at the Arundel Market, where he orders the hamburger or hot dog or, if he’s feeling a little fancy, the lobster roll.

“It’s only $10.99 with fries,” explains Stuart, who is 65, with a bushy white beard and a head of white hair he often keeps stuffed under a cap. “Pretty big, too.”

It’s not an extravagant life, certainly, but it makes him happy.


So when he recently won big playing the Maine State Lottery — not just once, but twice, for a total of $1.1 million within a single four-month period — he didn’t see much sense in changing things up, even after the money started rolling in.

The rolls of lottery winners might be filled with tales of lives altered following sudden riches, but Bobby Stuart’s has remained exceedingly constant.

“Ain’t nothing really different,” he shrugs, falling into the big leather recliner in the living room of his trailer. “I do the same thing over and over.”

Indeed, in the weeks since he won $1 million from a lucky scratch ticket — as well as another $100,000 just four months later — it would be almost impossible to tell. Stuart still calls the trailer home. Still clocks in for his 11-hour shifts at Hissong Ready-Mix & Aggregates. Still gets his supper at the same little restaurant every night after work.

To date, he hasn’t allowed himself any of the luxuries commonly associated with overnight wealth — new cars, fancy toys, lavish jewelry.

“I put new windows in my trailer,” he says, before quickly adding that he got a good deal on the job, from a friend of his son.


The son of a farmer, Stuart’s never been much for exuberance. He grew up doing tough work on the farm, learned how to make do with little. His lone annual splurge is attending a NASCAR race over in Loudon, N.H., once a year.

“That’s how we were brought up,” says Stuart’s sister, Becky Gosselin, who lives on the same patch of family land Bobby does. “So to be extravagant? No.”

Same goes for work.

Two giant checks for Robert “Bobby” Stuart, which he received when he won the lottery twice, on his couch at his home in Kennebunkport, M.E.Yoon S. Byun for the Boston Globe

The first weekday after winning a million dollars, he clocked in for his shift at Hissong Ready- Mix & Aggregates. He waited a week to turn in his first winning ticket because, as he explains it, it was the earliest his work schedule would allow him to make the hour-and-a-half drive up to lottery headquarters in Augusta.

When he won, everyone told him to hire a lawyer or an accountant to help him manage his winnings.

“Why should I pay those guys?” grumbled Stuart, who used a free financial adviser from his bank instead.

As for the trailer, he has no qualms.

His brother offered to come over with an excavator, tear down the aging trailer, and build a new one. But Stuart doesn’t much see the point. He’s got his recliner and his TV. Pictures of his family cover the walls and the refrigerator.

“Everybody I talk to says, ‘Why doesn’t he buy a new house?’ ” says Stuart’s 46-year-old son, Greg, who once won $250,000 from the state lottery himself. “I say, ‘He doesn’t want one.’ ”


Traveling doesn’t sound too bad, Stuart says, but he’s not sure where he’d go or who he’d go with.

If Christine were still around, maybe it would be different. They were married for 37 years, until that week two years ago when she went to the hospital with an illness and never came home.

Since then, he’s preferred to keep things the way they are.

He’s been happy, meanwhile, to share the wealth. He gave a portion of the winnings to each of his three children, telling them to do whatever they wanted with it. Whatever’s left in savings will be divvied up among them after he’s gone.

For the record, he has no plans to stop buying scratch tickets, even though everyone tells him he should quit while he’s ahead.

It’s something to do. And, anyway, who knows whether there might be another jackpot out there, waiting?

Last week, he stopped at a gas station and walked out with a couple of tickets.

He won $500.

Dugan Arnett can be reached at Follow him on Twitter @duganarnett.