"They were just so darned poor," said family friend Jim Colombe.
The sign to their ranch is broken, showing just how hard financial life's been lately.
The family was barely getting by selling scrap metal -- and they're reportedly behind nearly $4,000 in property taxes.
Just when it seemed things couldn't get worse, they got a whole lot better, reports CBS News correspondent Bianca Solarzano.
"I need some time to let this sink in …" said Neal Wanless, 23. Wanless was on his way to buy livestock feed when he decided to give luck a shot. He picked up Powerball tickets in the nearby town where he was born -- a place named Winner!
"I'd like to thank the Lord for giving me this opportunity and blessing me with this great fortune," said Wanless.
After a lump-sum payment and taxes, Wanless takes $88.5 million back to the ranch. And that's where he'll stay, he says, buy some extra land, keep working - and start helping.
"My family has been helped by the community and I intend to repay it back many times over,'' he said.
"That's just the way it is in this part of the state, people help people, we know one another,'' said Timothy Grablander, mayor of Mission, S.D., the tiny town where the Wanless ranch is.
On The Early Show Monday, Grablander described the Wanless family as a "typical ranch family" for that neck of the woods, "very down-to-earth, rural people.
Grablander said he's "sure" Wanless will keep his word and give back to the commnity.
A down on his luck cowboy who won big in a town called Winner -- is Hollywood listening?