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Jon Lester And The Cubs: A Match?

There are a lot of rumors out there about the soon-to-be free agent. Let's look at what some of the realities are.

Jon Lester, lost in thought in Oakland. Is he contemplating coming to Chicago?
Jon Lester, lost in thought in Oakland. Is he contemplating coming to Chicago?
Thearon W. Henderson

Jon Lester is just about the perfect match for the Cubs if they choose to go into big-time spending in free agency this offseason. He's an elite starting pitcher. He's lefthanded. He doesn't miss starts. He's got a long and positive history with the Cubs' current front-office team.

We've discussed the possibility of the Cubs signing Lester in various threads here, and I start this one primarily because of this article that was primarily aimed at a Red Sox fan audience, putting forth the possibility that Lester could return to Boston. There are, however, clues in there that Lester will go to the situation he finds best, and not necessarily for the most dollars:

"(The Red Sox) told me (after the trade to Oakland), ‘We’re going to be aggressive. You’re going to get blown out of the water by some of these (other) offers,’ " Lester told the Boston Herald. "I’m like, ‘I don’t need to be blown out of the water.’ Why would I need to be blown out of the water? That doesn’t make or break your decision, at least for me. I’m not going to the highest bidder. I’m going to the place that makes me and my family happy. If that’s Boston, it’s Boston." 

Of course, it’s easier to say that when generations of Lesters will be set for life, no matter where he signs. 

"In the greater scheme of things, we’re talking about just a stupid amount of money," Lester told the Herald. "For me, I want to be comfortable. The way I look at it is, if someone gives you $170 million and someone gives you $150 million, is that $20 million really going to change your lifestyle? Same thing if the highest bidder is $100 million and the team you’re going to feel most comfortable with offers $80 million. Is that $20 million really going to make the difference in your lifestyle?"

This is what I've said for quite some time -- that the "stupid amount of money" is going to be enormous and if Lester, say, made $20 million less from a situation that made him "comfortable," would he and his family really notice? There is a hint in the article that Lester might indeed return to Boston:

According to the Boston Herald, Lester’s 4-year-old son recently asked A’s closer Sean Doolittle if he played for the Red Sox.

"He thinks the house we’re staying in is a cool hotel for the weekend," Lester said. "He wants to know when we’re going home. So that’s hard."

Nevertheless, Lester would certainly be a good fit for the Cubs as they go forward into possible contention, if not in 2015, then perhaps in 2016 and beyond. 2015 might even be the year the Cubs are the sleeper pick of some to make the postseason -- if they go for a big-time pitching free agent like Lester (or, say, Max Scherzer).

It does seem as if Lester will choose the situation rather than the dollars, unlike Zack Greinke, who said he'd take the most dollars no matter who offered it:

"I could play for the worst team if they paid the most," Greinke said in an interview with "If the last-place team offers $200 million and the first-place team offers $10, I'm going to go for the $200 million no matter what team it was."

Every player is different and every situation is different. You can bet, though, that Lester won't do what Carl Crawford did when he signed with the Red Sox:

"I would like to think I know when it's time to make big decisions in your life you know to do a little more research," Crawford explained. "Look into a little bit more. I decided to sign with the Red Sox in five minutes. I didn't have no time to think about it. They told me this, bam, 10 minutes later I was signing with the Red Sox. It was one of those things I didn't look into it as much as I should have. I didn't call other players and ask around. I didn't do nothing. I just had my eye on one thing at the time."

Crawford made a lot of money: $142 million over seven years. But he certainly wasn't happy in Boston. Is he in Los Angeles? Who knows?

In any case, Jon Lester will choose the situation that's best for him personally. He'll get a lot of money no matter where he ends up. Should the Cubs sign him? Vote in the poll.