Connolly, John (1858–96), champion flat-racing jockey, was born in Naas, Co. Kildare, nephew of the famous jockey Pat Connolly. His uncle was champion in Ireland, and in England, where he won all the English classics in 1834, and the Epsom Derby twice. John was of slight build, and trained from an early age as a jockey. His brother, Pat, was also involved in racing and worked as a trainer at Curragh View for Tom Connolly (no relation). Together they trained Barcaldine, one of the greatest horses of the time, whom John rode unbeaten in a distinguished career in Ireland and England. Pat eventually took charge of the stable on the death of its owner.
In 1879, at the age of 21, John began to emerge as the outstanding flat jockey of his era, riding Soulouque to victory in the Irish Derby at the Curragh, Co. Kildare. He went on to win the Derby three more times in the course of his career, the first jockey ever to do so. Unlike most of his contemporaries Connolly concentrated exclusively on flat racing, and did not ride on other terrain. Similarly, he chose to compete on only the best courses, principally the Curragh, Baldoyle, Cork Park, and Down Royal. He was a stylish rider, and won plaudits for his technique, unlike his uncle, who was considered to have ‘an ugly Irish seat’. He won the Irish Derby again in 1883 on Sylph, in 1884 on Theologian, and in 1886 on Theodemir. Many of these victories were unexpected. One of his most difficult triumphs was his second Irish Derby win, on Charles Blake's filly in 1883. A fast-paced opening eliminated all the fancied runners, with Connolly and Sylph running out comfortable winners. Three years later Connolly again rode an unfancied mount and won a notable victory by outmanoeuvring the other jockeys and taking the highly desirable inner railing spot. He acted as a mentor for Michael Dawson (qv), who went on to ride five winners in his debut year (1882). Dawson later equalled Connolly's achievement of riding four winners in the Irish Derby.
Connolly's last big winner was on Angelus in the Railway Stakes in 1894. He died in April 1896 of pneumonia. He left one son, his wife having predeceased him. He was hailed the uncrowned king of the Curragh. He lived at Naas, Co. Kildare.