Don John, a bay colt by Tramp, was foaled in 1835. He won the St. Leger in 1838 for the Earl of Chesterfield, and went on to win the Doncaster Cup the same year, defeating the famous mare, Beeswing, the best racehorse in the North. In total, Don John won seven races between 1837 and 1839. Herring painted several other versions of Don John, one of which, with William Scott up before the start of the 1838 St. Leger, was engraved by Charles Hunt and published by S. & J. Fuller. He was later a successful sire.