After losing an 1898 horse race in the Bronx, New York, African-American jockey Alonzo ‘Lonnie’ Clayton, who had won the Kentucky Derby in 1892 at the age of fifteen, heard an insult from the crowd along the rail and struck a white spectator from Brooklyn across the face with his riding whip. The blow resulted in a two hundred dollar fine by the track stewards, but ultimately led to a civil trial, a financial judgment against Clayton that he ignored, and then an arrest and incarceration for non-payment of the judgment, which some writers mistakenly still claim was for race-fixing. Clayton had other financial difficulties as well that, compounded by his lack of success on the racetracks and decreasing opportunities for black jockeys, led him to sell both his large house and his commercial property in North Little Rock, Arkansas. After moving around the west and even to Vancouver, Canada, Clayton was working as a bellhop in California at the time of his death in 1917. The article also discusses the life of the man who was assaulted by Clayton, Henry Bolomey.