Background
Foaled in Kentucky, Sysonby was a bay son of the 1885 Epsom Derby winner, Melton, out of the English mare Optime by Orme (by the undefeated Ormonde). The mating of Melton and Optime was arranged by Marcus Daly, who was involved with the Anaconda Copper Mine. Daly died before Optime, stabled in England, foaled. His stock, including the still pregnant Optime, was brought to New York to be auctioned. James R. Keene purchased Optime for $6,600, sending her to his Castleton Stud in Kentucky, which he rarely visited.
Apparently Optime's foal, observed in his paddock, was anything but inspiring. Considered unattractive and small, as well as slow, young Sysonby was to be sent back to England for sale. But Keene's trainer, the well-regarded James G. Rowe, Sr., had seen Sysonby in action during some early trials. When it was time for the yearlings to be sent away, Rowe, a leading trainer who had once been a leading jockey (guiding Harry Bassett to his Saratoga Cup win amongst many other successes), covered Sysonby in blankets, convincing Keene he was too ill to make the long ocean journey.
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