Jon Lester Recalls 2014 Trade, Details Plan If Red Sox Didn’t Move Him

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Chicago Cubs pitcher Jon Lester

Photo via Ron Chenoy/USA TODAY Sports Images

A big what-if that hangs over the heads of Red Sox fans is what would have happened had Boston not traded Jon Lester to the Oakland Athletics in 2014.

Lester long was the Sox ace and in the years since he has shown no signs of stopping. But the 2014 Red Sox were floundering come July, and moving on from the then-30-year-old seemed like the right thing to do.

But had Boston not moved him, would it have increased their chances of re-signing him that offseason once he became a free agent? Prior to the 2018 Major League Baseball All-Star Game on Tuesday, Lester answered that question.

“My heart was still there even though I got traded, but when you’ve ground it out until that point and become a free agent you want to see what is out there. I feel like I still would have done that. I don’t know if the outcome would have been the same,” Lester said, via WEEI.com’s Rob Bradford. “I think if you’re able to get to that point you kind of have to eliminate that at the end of the day. Even though I got traded to Oakland, it was still the unknown of another place. You still go back to the Red Sox and the known. All my buddies were still there. It’s a hard question because it’s the unknown of what if they didn’t trade me and if that would have changed anything. I don’t know.

“I still would have gone through the process,” Lester added. “You don’t know if the teams would end up being the same because maybe the whole outlook of free agency would change. I would have had a qualifying offer hanging over my head. There are a lot of things that are factors in there that you probably can’t get the answers to without actually going through that scenario.”

Lester ultimately made out pretty well that offseason after playing half of a season with the A’s. He signed a six-year, $155 million deal with the Chicago Cubs, ultimately winning a World Series in 2016.

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