As a three-year-old, Jacobus' ran third behind winner Barnes in the mile and one-half Coney Island Derby at Sheepshead Bay. The biggest win of his career came in what would become the second leg of the U.S. Triple Crown series, the 1883 Preakness Stakes. In a two-horse matchup run over a mile and one-half at Pimlico Race Course, jockey George Barbee earned his third Preakness win by guiding Jacobus to a four length win over his only competitor, Parnell.[5]