The title story depicts the life of a jockey agent who has seen some bad breaks but knows in his heart he can turn things around if he can just get some "winter money" to make a fresh start in Florida. In "Chandelier," a bankrupt horse breeder risks everything again in an attempt to save a friend's farm. "Eldorado" is the story of a young horse groom convinced an old car will be good luck for him, even though it could break down over the next hill.
Life at a race track is as desperately unpredictable as the next race, but the people bound to this life live only when they are taking chances. The lies they tell themselves and others run with reality to create new truths. The men and women of Winter Money live in motel rooms that rent by the week, where strangers can change the course of lives. Love and compassion come from unexpected sources, and, as a result, dreams and desired are nurtured and sometimes, against the odds, sustained.
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