Myers entered 2014 as the Rays' everyday right fielder. On May 4, Myers hit his first career inside-the-park home run. During a game against the Boston Red Sox on May 30, Myers collided with Desmond Jennings while attempting to catch a fly ball, resulting in a stress fracture in Myer's right wrist which required a cast and significant rehab time. Myers returned to the club on August 20, initially slotted as a DH before returning to the field.
In 2014, he batted .222/.294/.320 with six home runs and 35 RBIs in 325 at bats.
On December 19, 2014, the Rays traded Myers, Ryan Hanigan, and Jose Castillo to the San Diego Padres as part of a three-team transaction, in which the Padres traded Jake Bauers, Burch Smith, and René Rivera to the Rays, the Padres traded Joe Ross and Trea Turner to the Washington Nationals, and Washington traded Steven Souza and Travis Ott to Tampa Bay.