Lester was a longtime favorite of the Cubs' current front office when Theo Epstein ran the Red Sox for a decade. Epstein signed him to a five-year extension worth $30 million in 2009 which included a team option for $14 million for this season. Now, at age 30, Lester likely will be a free agent for the first time in his career.
"They always treated me with the utmost respect and class," Lester said this week of Epstein and the front office. "I have nothing but good things to say about them."
Lester wouldn't comment specifically about the Cubs, but it's been well reported that a new deal with the Red Sox doesn't seem imminent. The Cubs might open their purse strings for a player such as Lester, who's reportedly already turned down a four-year, $70 million extension from Boston. That offer seems way below market value.
"If you're in that position you do your homework," Lester said about free agency. "Obviously, there's the familiarity with those [Epstein] guys. That's kind of predicting the future and possibly be putting a foot in my mouth which I don't want to do."
Lester is 9-7 this season with a 2.92 ERA. He's made at least 31 starts in each of the past six seasons since becoming a full-time big league player and beating cancer in 2006-2007. That kind of durability is going to be attractive to teams, although no one knows what his asking price is or what the market for him will look like.
The Cubs reportedly offered Jeff Samardzija five years at $85 million, so maybe a deal could get done with those kinds of numbers. But more than likely it would take much more. The Cubs might go higher if they believe in him as an ace, something that's in question with Samardzija.
"Watching them and looking at them it seems like they are pretty close to being there," Lester said of the Cubs. "Maybe one or two players away from putting it together."
Lester had only good things to say about Chicago adding his wife "never misses that trip." He also knows that Cubs fans are "fanatical."
"They do such a good job no matter who it is, they make it attractive to go there," Lester said. "Next year or two will be good for them. I know what (Epstein's) able to do."