Jaime Diaz began his dance studies with Anna Pavlova's Ballet Academy in Bogota under the tutelage of his father. Later he studied at the Cuban National Ballet School and joined the National Ballet of Cuba as a soloist in 2000. Diaz joined Boston Ballet in 2004 as a member of the corps de ballet and was promoted to soloist in 2008.
His repertory includes Bournonville's La Sylphide, Ashton's La Fille mal gardée, Kudelka's Cinderella, Kylian's Saraband, Caniparoli's Lambarena, Morris' Up and Down, Forsythe's In the middle, somewhat elevated, Messerer's Spring Waters, Nuryev's Don Quixote, Balanchine's Agon and Theme and Variations, and Robbins' Afternoon of a Faun. He also performed roles such as Albrecht in Giselle, Romeo in Cranko's Romeo and Juliet, Franz in Balanchine's Coppélia, and Solar in Clerc's La Bayadère.