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#1
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This is extremely obscure but in the late '80s in northern california there was a horse named Tootsiepop who finally broke her maiden in her 27th start after finishing 2nd or 3rd 13 times and IIRC always (or almost always) went off at 3-1 or less.
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#2
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Aguila,was the horse around the same time that a co worker of mine played and lost everytime he started. A closer at Santa Anita that never got there.
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#3
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There was a horse in California a few years back named King Palm who was second in a bunch of maiden races before he finally won, nearly always as a favorite. He wasn't a bad horse - his lifetime record is 26/2-12-2 and $185,420 in earnings - but he was a beaten favorite way too often.
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