Medina started practicing boxing as a kid. Medina would sneak out of his parents' house to practice at a boxing gym. They were unaware of the fact that Medina practiced boxing until he made the newspapers due to his early success. Medina won multiple medals representing Sonora at nation-wide competitions.
Professional career
Medina debuted as a pro in June 2007, at the age of 19. In 2008, he won the WBC FECOMBOXsuper middleweight title. Following his March 2010 win over Demetrius Davis, Medina suffered two fractures in his right hand. The injury kept him sidelined for 8 months. Medina won his first 22 fights, 16 of them by way of knockout. On December 17, 2010 Medina faced undefeated Gilberto Ramírez for the vacant WBC Youthmiddleweight title. The bout was held at the Gimnasio German Evers in Mazatlán, Sinaloa, Mexico. Medina was knocked down in round 6 before the referee waived the count, giving Ramírez the win. Medina then suffered another TKO loss to veteran Yori Boy Campas. Medina suffered a series of losses against the likes of José Uzcátegui and Badou Jack over the next few years, but a knockout win over highly-touted prospect J'Leon Love on August 2014 vaunted him into world title contention. Medina was able to corner Love against the ropes and then caught him with a left hook that knocked Love out cold. After José Uzcátegui was sidelined due to illness, Medina became the mandatory challenger to IBF champion James DeGale. The fight was scheduled to take place on 30 April 2016 at the DC Armory in Washington, DC. DeGale outpointed Medina in a harder than expected fight. DeGale won on all three judges scorecards. The fight averaged of 342,000 viewers and peaked at 397,000 on Showtime. Medina threw over a thousand punches during the fight and he had some success cutting offthe ring and cornering DeGale, but DeGale was ultimately able to win the fight with his skills, landing about half of his punches. Medina was knocked out by David Benavidez on May 2017 in a WBC eliminator. On round 8, Benavidez landed an incredible flurry of punches to Medina's face that ended the fight in dramatic fashion. Medina was dropped twice during the fight.