[1] An African American, Simms began racing in 1887 and was one of the most successful jockeys using the short-stirrup style (which gave the rider a crouching posture).

En route to winning the United States riding title in 1893 and 1894, Simms won back-to-back Belmont Stakes.

Back in the United States, Simms won the 1896 Kentucky Derby in its first running at 1¼ miles on Ben Brush.

[5] During his 14-year career, Willie Simms rode some of the great Thoroughbred racehorses of the day such as two-time American Horse of the Year, Henry of Navarre.

Willie Simms finished his riding career with 1,125 wins and in 1977 was inducted into the National Museum of Racing and Hall of Fame His name was frequently misspelled as "Sims" by media of his era.