Jackie Bradley Jr.’s career as one of baseball’s most underrated defenders may be in the rear-view mirror.

The 33-year-old outfielder is expected to retire after an 11-year career spent mostly in a Red Sox uniform, MLB insider Jon Heyman reported this weekend.

Boston drafted Bradley No. 40 overall in the first round of the 2011 MLB Draft and he made his Major League debut on Opening Day 2013. He’ll retire with an All-Star season, a Gold Glove Award and two World Series rings to his name.

That Bradley only won one Gold Glove in 2018 belies how reliable and spectacular he was defensively (though he was a finalist in several other seasons). For years he was a one-man highlight reel in Fenway’s tricky center field, leaping and diving to make jaw-dropping leaping catches and scaling walls to rob hitters of home runs. Thrice between 2014-17 he was top-10 in the American League in Defensive Wins Above Replacement; his career 10.3 dWAR currently ranks 19th among active players. He led AL center fielders in putouts in ‘16 and ‘19, and had six top-10 seasons in CF assists, including leading the league in ‘14, ‘16, ‘18, and ‘19.

While he’s still technically an active player, it must be noted that among active outfielders, he’s 10th in defensive games, sixth in putouts and fifth in assists. He’s also MLB’s active leader in double plays turned by an outfielder.

Though an inconsistent hitter overall, Bradley had flashes of brilliance at the plate. On Aug. 15, 2015, he joined a small group of modern Major Leaguers with five extra-base hits in a single game. The following spring, he earned American League Player of the Month honors with a 29-game hitting streak, which tied the fourth-longest mark in Red Sox history. 2016 was his lone All-Star season.

Most memorable was his performance in the 2018 postseason. While several of his more offensively-inclined teammates struggled, his three extra-base hits – including two go-ahead knocks and a grand slam – and nine RBI in that year’s ALCS and propelled Boston to the World Series (when he homered again) and their eventual championship, and he earned series MVP honors.

After eight seasons with the Red Sox, Bradley became a free agent in November 2020. He signed a two-year contract with the Milwaukee Brewers and was a Gold Glove finalist again in 2021, but his departure was short-lived. Boston acquired him again the following offseason, and he played another 91 games for the Red Sox.

When they released him in early August, he immediately signed with their division rival Blue Jays. Two weeks later, he returned to Fenway and helped Toronto sweep Boston, contributing two hits, an RBI, and scoring three runs. At season’s end he was a Gold Glove finalist once more, and he spent his final season with the Kansas City Royals, playing 43 games before being released in June.