Milwaukee Brewers Gwynn was drafted by the
Milwaukee Brewers in the 2nd round of the
2003 MLB draft. After a couple of years in the minor leagues, he made his major league debut on July 15, , as a pinch hitter against the
Arizona Diamondbacks. His first major league
hit on July 19 (against
San Francisco Giants closer
Brian Wilson) came exactly 24 years to the day of his father's first major league hit — both
doubles. Towards the end of the 2006 campaign, Gwynn received more playing time, replacing
Brady Clark in the lineup. He appeared in 32 games for the Brewers in 2006, hitting .260 and made the Brewers' opening day roster for . Late in the 2007 season, the
San Diego Padres were in Milwaukee attempting to clinch a playoff berth.
Closer Trevor Hoffman was one out away from sending the Padres to the playoffs, but the tying run was on
second base. Gwynn
pinch-hit for
Bill Hall against his dad's former team, and dramatically tied the game with a
triple. The Padres would go on to lose the game as well as the season finale on the next day, opening the door for the
Colorado Rockies to force a one-game playoff with San Diego. The Rockies defeated the Padres in a wild contest, keeping them out of the postseason. With a focus on defense, Brewers manager
Ned Yost indicated in March that Gwynn and
Gabe Kapler might have a leg up on
Gabe Gross for an outfield position; this became true when Gross was traded to the
Tampa Bay Rays on April 22, 2008. Gwynn was optioned to the
Nashville Sounds of the Triple-A
Pacific Coast League on May 25, 2008, but recalled after rosters expanded on September 1. In 3 years with the Brewers, Gwynn hit .248 in 130 games.
San Diego Padres on July 19, . On May 21, 2009, Gwynn was traded to the
San Diego Padres for outfielder
Jody Gerut. Gwynn was informed of the trade by a phone call from his father, who played his entire career with the Padres. In his first game with the Padres, the same day he was traded, Gwynn pinch-hit in the 9th inning. He drew a walk and then scored the winning run. In two seasons (236 games and 682 at bats) with the
San Diego Padres, Gwynn Jr. accumulated 165 hits, 20 doubles, 9 triples, 5 home runs (2 of which were inside the park), and 41 RBI, with a .242 batting average. Gwynn wore the number 18 with the Padres, with his father's number 19 having been retired.
Los Angeles Dodgers Gwynn agreed to a one-year contract with the
Los Angeles Dodgers on December 8, 2010. He played in 136 games with the Dodgers in 2011, the highest total of his career, and hit .256 with 22 stolen bases. On June 1, 2012, Gwynn was part of a Dodgers lineup featuring the sons of five former Major Leaguers (along with
Jerry Hairston Jr.,
Iván DeJesús Jr.,
Dee Gordon and
Scott Van Slyke), being the first time in Major League Baseball history that this had occurred. In 103 games in 2012, he hit .232 with 13 stolen bases. Gwynn was designated for assignment on August 6, and accepted an assignment to the Triple-A
Albuquerque Isotopes, where he hit .338 in 19 games. Gwynn spent the entire 2013 season with Albuquerque, where he hit .300 in 104 games.
Philadelphia Phillies On December 24, 2013, Gwynn signed a minor league contract with the
Philadelphia Phillies containing an invitation to Major League spring training. At the end of spring training, it was announced that Gwynn had made the Opening Day roster to start the 2014 season, which culminated a "long road" back to the major leagues. He was the Phillies' opening day starter in left field (
Domonic Brown, the projected starter in left field, started at
designated hitter as the Phillies opened the season on the road against the
Texas Rangers), and batted in the ninth position. Later, when
Ben Revere had sore ribs, Gwynn started and batted in the
leadoff position, and because of his performance, started several games after Revere had recovered. Following the death of his father, Gwynn Jr. was placed on the bereavement list on June 16. He was designated for assignment on July 21, and released on July 28. Gwynn later re-signed to the Phillies on a minor league contract on August 3, and was assigned to their Triple-A affiliate, the
Lehigh Valley IronPigs. He was called back up by the Phillies on September 2. On October 10, Gwynn refused assignment to Triple-A and was released.
Washington Nationals On March 2, 2015, Gwynn signed a minor league contract with the
Washington Nationals. In 89 appearances for the Triple-A
Syracuse Chiefs, he slashed .255/.327/.332 with one home run, 27 RBI, and 10 stolen bases. Gwynn elected free agency following the season on November 6. ==Post-playing career==