Martin's technique was often at odds with racing authority rules, his license being suspended several times, and his early career was marred by allegations of cheating and underhanded gambling practices.

[4] Weighing only 80 lbs and standing at barely five feet tall, Martin soon acquired the nickname of "Skeets" because he looked like a tiny mosquito while riding a large Thoroughbred.

In 1897, he won the Brooklyn Handicap on Howard Man while racing for George E. Smith, the notorious gambler called "Pittsburgh Phil."

In 1899, Martin was contracted to ride for John Daly and the Dwyer Brothers, notably securing second place on Half-Time in a rousing nose-to-nose finish with Jean Bereaud at the Belmont Stakes.

[7] In June 1899, Martin became part of the "American invasion" of jockeys that greatly influenced and dominated British horse racing in the early twentieth century.

[10] Sloan and Martin, in the company of bicyclist and future racecar driver, Eddie Bald, returned to the United States in December 1899 due to the curtailing of turf events at the outbreak of the Second Boer War.

Returning for the 1900 season, Martin won the Brocklesby Stakes and Doddington Plate in March, but his aggressive riding style often led to trouble.

He was suspended by the Jockey Club for foul riding from May to June due to his being disqualified in the Spring Two-Year-Old Plate at Kempton Park.

The Jockey Club refused to renew Martin's license for the 1901 season due to his continued disregard for racing etiquette and rough riding style.

At the onset of World War I in 1914, Martin and his wife Florence left their residence in Newmarket and moved to California, returning to the UK in 1916.

Collections were taken in his name by friends in the United States and Europe under the name "Skeets Fund,"[19] but the money could not be transferred safely during World War II.