Brown, Ben Brush began racing in Louisville. In his first race at two, he won by five lengths. In his second start, he came home by three lengths. His third effort saw him gallop home ahead of the good horse Nimrod. Ben then went to Ohio, winning the Emerald Stakes and the Diamond Stakes. After five wins in five starts, Ben Brush went to New York, where he ran third at Sheepshead Bay but then won an overnight handicap, giving 19 pounds to his nearest rival. He then lost to the high-class Requital in the Flatbush Stakes. He ran out of the money for the first time in the Great Eastern Handicap but won the Holly Handicap. At this point, he was sold to the famous gambler Mike Dwyer, who had, with his brother Philip, raced his sire Bramble as well as the champions Hindoo, Hanover, Miss Woodford, and Luke Blackburn. Ben Brush was the last champion to carry Mike Dwyer's colors. The reported sum was $18,000. (A race for three-year-olds, the Dwyer Stakes, held at Belmont Park since 1918, was named in their honor.) Now ridden by Hall of Famer Willie Simms, an African-American considered one of the greatest riders of his day, and trained by Hardy Campbell Jr., Ben Brush won six more races as a two-year-old. He earned $21,398 with 13 wins in 16 starts. In 1895, he was Champion Two-Year-Old Colt. At this point, Walter Vosburgh said he "could have beaten any three-year-old of that season." (Willie Simms also rode in England, where he was the first to introduce the short-stirrup style. After his stint in Europe, he was retained by Dwyer as his stable rider, but such was Simms's stature that he had the freedom to accept mounts from other stables as well. The nation's leading rider of 1893–94, he remains the only African-American jockey to have won the Derby, Preakness, and Belmont.) 1896: Three-Year-Old Season Ben Brush's first race in his 1896 season was the Kentucky Derby. Without benefit of a prep race and having never run farther than seven furlongs in his career, he stumbled badly coming away from the barrier, nearly unseating Simms. By the time they recovered, the race seemed over for Ben Brush, but he made a tremendous move on the backstretch, caught First Mate on the turn for home, and battled fiercely with Ben Elder down the stretch before