Did jeopardy losers ever keep their winnings?

yes, but not really because it was a different show. It was a network show with Art Fleming as host and not the Popular Jeopardy series. Since this show started in 1984 Jeopardy losers did not keep there money. Some of the early shows prizes for questions were 10 through 50 dollars until it was cancelled in 1975. Even when brought back in 1978-9 the top prize was 125 see related link