At age 16 in 1986, Gryder began his career as a professional jockey in Tijuana, Mexico at Agua Caliente Racetrack.

[1] Gryder returned to the United States to ride at Santa Anita Park.

[3] Gryder has also won several Leading Rider titles at Churchill Downs, Arlington Park, Aqueduct Racetrack, and Golden Gate Fields.

[4] In 2009, Gryder rode Well Armed to a win in the world's richest race, the $6,000,000 Dubai World Cup, finishing 14 lengths in front of Gloria De Campeao, the largest margin of victory in the history of the race.

[1] He joined Stronach Group in 2021 as Vice President of racing industry relations.