G. Stevens won the Grand National five times, in 1856, 1863, 1864, 1869 and 1870, and won the Kentucky Derby three times, in 1988, 1995 and 1997.
Of course, it isn't the same G. Stevens; the Grand National winner was George Stevens and the Kentucky Derby winner was Gary Stevens. But it's probably the closest to an answer you can get, since no jockey has won both races.
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