Beltrán de Osorio y Díez de Rivera

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Beltran de Osorio y Diez de Rivera (1919-1994), a Spanish aristocrat known as the "Iron Duke" of Alburquerque, was an amateur horse jockey who became obsessed with winning Britain's Grand National Steeplechase horse race when after watching a film of the race on his eighth birthday. However, each of his attempts ended in failure.

On his first attempt in 1952, he fell from his horse, but woke up later in hospital with a cracked vertebra.
He tried to win again in 1963, and fell from his horse yet again. (Bookies placed a bet of 66-1 against him finishing still on the horse).
He raced again in 1965, but again fell from his horse after it collapsed underneath him, breaking his leg.
In 1974, after having sixteen screws removed from a leg he had broken after falling in another race, he also fell while training for the Grand National and broke his collarbone. He then competed in a plaster cast in the race, this time managing to finish, but only in eighth place.
One anecdote from this race is that he barged into Ron Barry at second Canal Turn; Barry said "What the **** are you doing?", to which he replied: "My dear chap I haven't a clue...I've never got this far before!"
In 1976 the duke fell again during a race, this time being trampled by other horses. He suffered seven broken ribs, several broken vertabrae, a broken wrist, a broken thigh, and a severe concussion which left him in a coma for two days.

At 57, the Iron Duke still tried to compete, but officials pulled his license for "his own safety". He never won the Grand National, but broke more bones than any other jockey in attempting to do so.