How does Paul determine the names of the winning horses in Rocking Horse Winner? Does Paul always pick a winner?  How did he learn about horse-racing in the first place?

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Paul notices the whisperings of his house that "There must be more money!"—most likely the personification of his parents' struggles to pay their bills due to "the social position they had to keep up"—and seeks to find a way to stop the voices. He discovers that when he rides his...

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Paul notices the whisperings of his house that "There must be more money!"—most likely the personification of his parents' struggles to pay their bills due to "the social position they had to keep up"—and seeks to find a way to stop the voices. He discovers that when he rides his big rocking horse, he is able to go into a trance-like state and learn the name of the next winner of the horse race.

Paul originally learns the ins and outs of horse racing from Bassett, the gardener. The two have many conversations about the winners before Uncle Oscar is made aware of the situation. Sometimes he is certain of the winner, and sometimes he isn't:

"Oh, well, sometimes I'm absolutely sure, like about Daffodil," said the boy; "and soetimes I have an idea; and sometimes I haven't even an idea . . . Then we're careful, because we mostly go down."

Paul goes through a spell when he isn't sure about any winning horses, and he begins to grow more tense because he senses that his mother needs more money, even though Paul has presented her with quite a nice sum for her birthday. He becomes resolute in learning the name of the winner of the Derby.

In the end, the boy's desires to please and comfort his mother drive him to ride himself to his own death.

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Paul determines the names of the winning horses by riding his wooden rocking horse.  If he can ride his horse until he "gets there", he receives a kind of revelation so that he is "absolutely sure" which horse will win the next race.  It is a frightening experience when Paul rides to this extent, because he urges his horse on with an intensity which borders on frenzy, "madly surging", seemingly possessed by a strange, inner power.  Paul is never wrong, however, when he is "sure"; and it is in this manner that he was able to predict that the longshots Daffodil and Malabar would win the Lincoln and the Derby, respectively.

Paul does not always pick a winner - "sometimes (he) (has) an idea, and sometimes (he) (hasn't) even an idea".  Then, when he is not "absolutely sure", he "mostly go(es) down", betting wrongly and losing money.  After he was correct about the Lincoln, he took a chance on the Grand National, but because he had not really "known" which horse would win, he had lost a hundred pounds. 

Paul learned about horse racing from Basset, a young gardener who is "a perfect blade of the 'turf'...he live(s) in the racing events".  Paul had come to Bassett and asked what he knew about horse racing, and Basset had lent him his "first five shillings, which (he) lost".  Bassett is so involved with racing that he speaks of them "as if he were speaking of religious matters".

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