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The Last Derby: A Novel of Jimmy Winkfield
Paperback
Series: The Winkfield Trilogy, Book 1
General FictionHistorical Fiction
Publisher: Inkylines & Words
Published: Nov 7 2026
Pages: 276
Weight: 0.82
Height: 0.62 Width: 6.00 Depth: 9.00
Language: English
Two garlands of roses in two years. Then his own country closed the door on him, one Tuesday at a time.
He is born in Chilesburg, Kentucky, in 1880, the youngest of seventeen children, and by the time he is old enough to be useful, both parents are in the ground. He walks to Lexington and finds the racetrack, the one place in the state where a small boy's size is worth money. He rides his first race at Hawthorne in 1898, causes a four-horse spill, and draws a year's suspension before he has properly begun. He comes back with quiet hands.
By 1901 he is the best rider in the American West. Derby morning breaks gray with a night's rain sitting in the track, and he is out walking the ground before the lamps go down, crumbling dirt through his fingers, and what they report becomes the plan: slow going taxes the ones who chase. He puts His Eminence on the lead and lets him breathe his own air for a mile and a quarter, wire to wire. He rides one hundred sixty-one winners that year, and the official turf guide records the achievements of Black riders with diminishing care.
The second Derby is the one the trade still argues about. Two colts in one barn, a rival who has to be maneuvered onto the wrong one, and a public trial run in front of the whole clocker colony for the sole purpose of telling a lie with a horse. Alan-a-Dale wins at long odds by a nose on legs coming apart underneath him, and when they ask how he managed it, he gives them the sentence that outlives him: I was riding four horses.
Then the weather turns. Nobody votes on it, and no man enforcing it will admit it exists. A starter says a word to him in front of a full grandstand in 1903, and he carries it into the race, moves too soon on the favorite, loses by three-quarters of a length, and is still blaming himself fifty years later. In September he takes three thousand dollars from a stranger at a rail, breaks his word to John E. Madden, finishes nowhere in the Futurity, and gives a country that has spent two years building a case against him the fact it needed. In March an envelope comes up the walk on Corral Street with the Tsar's eagles down one side.
He won the Kentucky Derby twice before he was twenty-three. No Black rider has won it since.
THE WINKFIELD TRILOGY follows Jimmy Winkfield across three volumes and ninety-two years, from a settlement of seventeen children in Kentucky to the winner's circles of two empires and back to a Louisville front door. The wins are all real.
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