Dustin Pedroia Shares Funny Story About Only Time He Faced Jon Lester

Jon Lester never pitched against the Red Sox in his career, and Dustin Pedroia never played for a team other than Boston. So, the two never went toe-to-toe during a Major League Baseball game.

But there was this one time in 2005…

ESPN’s Jesse Rogers caught up with some of Lester’s former teammates with the 38-year-old hurler announcing his retirement Wednesday. They shared stories about Lester’s work ethic, leadership and durability and expressed admiration for all he accomplished, on and off the field.

Pedroia recalled the only time he ever stepped into the batter’s box against Lester. It happened during a spring training batting practice in 2005, before either player reached the majors.

“I knew I could get under Jon’s skin,” Pedroia told Rogers. “He wasn’t telling me what he was throwing so if he threw a cutter, I would just take it or let it hit me, I didn’t care. So when he threw me a two-seamer, I hit a missile right back off the L-screen.

“I talked so much trash to him after that. And I made it a point, I’m never going to face him again. I swear, if we played him in a regular-season game, I would have taken a day off and sat out there with a Mai Tai.”

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Lester, a second-round pick in 2002, and Pedroia, a second-rounder in 2004, both made their big league debuts in 2006. Before long, they became household names in Boston, with Pedroia earning American League Rookie of the Year honors in 2007 and Lester securing the win in Game 4 of the World Series that year despite missing part of the season while battling cancer.

The two stayed teammates until 2014, when the Red Sox traded Lester to the Oakland Athletics. Lester considered a return to Boston that offseason but ultimately signed with the Chicago Cubs, beginning a six-year run in the Windy City that ended in 2020. The southpaw spent 2021 split between the Washington Nationals and St. Louis Cardinals.

“In the back of my mind, I always thought we would re-sign him,” Pedroia, who retired last February, told Rogers. “He called me right before he signed with the Cubs. He was crying. That was probably the hardest moment in my big league career. It was late. I was in bed and he called me. I was like ‘Jon, it doesn’t change how I feel about you.’ That was worse than any loss that I had on the field. He was family.”

Lester and Pedroia were two amazing competitors. It would have been fun to see the latter dig in against the former at least once during the regular season, but the Red Sox surely are glad to have had both players on their side for such an extended period.