Kyle Brasseur, ESPN 9y

Jon Lester 'probably' would have taken 5-year, $120M Red Sox extension last spring

By now it's clear the Boston Red Sox's initial extension offer of four years, $70 million to left-handed pitcher Jon Lester during spring training wasn't enough for the two sides to get a deal done.

But, hypothetically, say the Red Sox offered Lester a deal similar to the one Philadelphia Phillies left-hander Cliff Lee got as a free agent in 2010 -- five years, $120 million. Would Lester have taken that deal?

"You go back in time and you look at it and you go, 'Probably, yes,' Lester said Thursday night in an appearance on WEEI's Hot Stove show. "But you don't know. It's one of those deals where when it's sitting in front of you, that's a lot of money to turn down. That would have made it very difficult to turn down."

Instead, after being traded to the Oakland Athletics at the trade deadline, Lester made it to free agency once the season was over, signing a six-year, $155 million deal with the Chicago Cubs. The Red Sox's final offer was for six years and $135 million, a value general manager Ben Cherington described as the best the team could do.

Although many feel the Red Sox's initial offer to Lester was an insult -- especially given how high the market went after the season -- Lester said he was in no way insulted by the offer.

"I think that's an easy topic to pick on for a lot of people. We're all men. We all understand what they were trying to do. By no means was I insulted. By no means were my feelings hurt," Lester said. "They had a game plan and we had a game plan and we went into it with our plans. Just, for whatever reason, we couldn't get anything done before the [2014] season started."

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