As a three-year-old he finished third in the 2000 Guineas and was unplaced in The Derby before winning the Sussex Stakes at Goodwood and the St Leger at Doncaster in September.

Apart from Black Jester, he sired the Derby winners Pommern, Humorist and Fifinella and through his son Phalaris is the direct male-line ancestor of most modern Thoroughbreds.

[6] Her later descendants included the classic winners Royal Palace, Fairy Footsteps (1000 Guineas) and Light Cavalry (St Leger).

[11] He was however, regarded as one of the most promising British colts of his generation, and with The Tetrarch being considered unlikely to contest the classics, he was identified as a contender for major honours in 1914.

[12] In the 2000 Guineas over Newmarket's Rowley Mile course, Black Jester finished third of the eighteen runners, beaten a short head and two lengths by Kennymore and Corcyra.

[8] Shortly afterwards, Black Jester won the St George Stakes at Liverpool to confirm his position as a contender for the Epsom Derby.

[13] At Epsom on 29 May, Black Jester started the 10/1 second favourite for the Derby, which attracted an estimated 400,000 spectators, including the King and Queen.

He briefly appeared to take a slight lead[14] but was overtaken by the French-trained outsider Durbar and dropped out of contention in the closing stages to finish seventh of the thirty runners.

Ridden by Walter Griggs,[19] he tracked Kennymore, who set an extremely strong pace, until taking the lead quarter a mile from the finish.

[21] In his remaining races that year Black Jester finished unplaced under a weight of 124 pounds in the Cambridgeshire Handicap[22] and second to Hapsburg in the ten furlong Champion Stakes at Newmarket.

[25] At the same course a month later, he was beaten by the three-year-old Rossendale in the Princess of Wales's Stakes, when attempting to conceded twenty-one pounds to the younger horse.