Gomez learned to ride by watching his father, Louie, who was a jockey at many tracks in the Southwest United States. When Gomez was in the tenth grade, he dropped out of school to start his career as a jockey, and began riding at Santa Fe Downs in New Mexico in September 1988, picking up his first victory at that venue aboard Furlong Circle. After a stint riding on the California Fair Circuit, Gomez switched his tack to the Midwest and rode at Ak-Sar-Ben and Fonner Park in Nebraska. Gomez was the second leading apprentice rider in 1989, racking up 182 winners. In the mid 1990s, Gomez's career began to take off. He won back-to-back runnings of the Arkansas Derby in 1994 (with Concern) and 1995 (with Dazzling Falls). Two years later, he captured the "Mid-America Triple" at Arlington Park by winning the American Derby, Arlington Classic, and his first Grade I, the Secretariat Stakes, all aboard Honor Glide. After battling substance abuse issues and serving jail time in 2003, Gomez returned to riding in 2004. He was able to regain his previous success, and by the end of 2005, not only had he conquered his personal demons, he was one of the top go-to jockeys in the business. Gomez has continued to enjoy more success in the last few seasons. He won the Eclipse Award for the Outstanding Jockey again in 2008 and was a finalist for that award in both 2009 and 2010, and wound up winning four straight earnings titles until that streak was snapped in 2010. Among his many Breeders' Cup races wins is the 2010 Classic aboard Blame. Gomez is one of 5 jockeys to be considered for induction into racing's Hall of Fame for 2013.