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After a successful season in 2000, SkyJack incurred a knee injury that required multiple surgeries. In addition, he suffered from bouts of colic, all of which kept him out of racing until September 2002. Having recovered from life-threatening illnesses, the gelding enjoyed his most successful season, winning the Grade II Mervyn Leroy Handicap and the Grade I Hollywood Gold Cup. In winning the 2003 Longacres Mile Handicap, SkyJack set the record for both the fastest time and widest margin of victory.
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