Henry Gribbohm believes he was ripped off by the game, called Tubs of Fun, where contestants toss balls into a tub (hence the name).
But he quickly ran out of fun, and money.
Gribbohm, 30, of Epsom, N.H., dropped $300 in just a few minutes, then says he went home to get $2,300 more and soon lost all of that as well, according to CBS Boston.
He told the station the $2,600 was his life savings.
Gribbohm says he was attending a Manchester carnival run by New Hampshire-based Fiesta Shows and wanted to win an Xbox Kinect at the Tubs of Fun booth. He says when he practiced it was easy, but something changed when he started playing for the prize and the balls kept popping out.
"It's not possible that it wasn't rigged," said Gribbohm.
He says he kept trying to win back his money by going double or nothing.
"You just get caught up in the whole 'I've got to win my money back,'" he said.
Gribbohm says he went back to the booth the next day to complain, and the man running the game gave him back $600. Henry filed a report with the Manchester Police Department.
Carinval operator Fiesta Shows says the game is run by an independent contractor who has worked for Fiesta for years. Fiesta tells CBS Boston it is interviewing the contractor to "get to the bottom of what happened" and the game is not being set up at an upcoming carnival in nearby Derry.
"They've been with us quite a while," said Fiesta Vice President John Flynn. "First I ever heard of anything like that."
Flynn said he did not know the name of the contractor off hand, and said it was "pretty next to impossible" to lose such a large amount of money at the game.
Manchester Police Lieutenant Maureen Tessier says the department is investigating to determine if there was any fraud.
Gribbohm says he is considering a lawsuit.
"For once in my life I happened to become that sucker," said Gribbohm. "It was foolish for putting up my life savings."