He was first drafted by Milwaukee Brewers in the 2nd round of the 2003 MLB draft. Tony played in the team’s minor leagues for a couple of years and had his first major league debut on July 15, 2006. In March 2008, Brewers manager Ned Yost indicated that Gwynn and Gabe Kapler might have a leg up on Gabe Gross for an outfield position.
Tony was later traded to the San Diego Padres for outfielder Jody Gerut on May 21, 2009. In his first game, he drew a walk and then scored the winning run. After two seasons with the team, he had accumulated 165 hits, 20 doubles, 9 triples, 5 home runs, and 41 RBI, with a .242 batting average wearing a number 18 jersey.
Futhermore, he agreed to a one-year deal with the Los Angeles Dodgers on December 8, 2010, he made .256 hits with 22 stolen bases. Tony spent the entire 2013 season with Albuquerque, with hit .300 in 104 games. In addition in December 2013, he signed a minor league contract with the Philadelphia Phillies. Tony began batting in the leadoff position after Ben Revere had sore ribs. After the death of his father he was placed on the bereavement list on June 16, 2014, and signed a minor league contract with the Phillies on August 3. He refused assignment to Triple-A and was released on October 10, 2014.
