Lose One's Shirt(lose a great deal of money)
I happened to bump into Doug at lunch yesterday afternoon.
What's new with Doug these days?
He wasn't doing so well. For one thing, he told me he lost his shirt at the races.
Doug has always liked to bet on the horses. I'm not surprised that he lost a great deal of money.
Yeah. At this rate he'll never have a penny to his name!
have 〜 to one's name = 〜を自分のものとして所有している
He doesn't have a dollar to his name.｢自分の金は一銭もない」