 Boston had established himself as a great—if tempestuous—race horse and more than once, his then owner (Colonel W. R. Johnson, called the "Napoleon of the Turf") was paid good money "not" to race, in order to encourage other owners to enter their horses in an event.The accepted wisdom is that Boston lost on his merit only once.In May 1842, he met the filly Fashion, the daughter of Trustee and Bonnets o' Blue, in a well-touted match race at the Union Course on Long Island, New York.