Theo's a smart guy. Signing pitchers over 30 usually doesn't turn out very well. I don't think it makes sense for Theo to go 6 or 7 years on Lester. The Cubs will be OK this year but it may be another 2-3 years before that Cubs team is rolling and now Lester is 33-34. It's smarter to sign some cheaper mid-range guys and go big next year when Jordan Zimmerman, Cueto, Fister, Iwakuma, Latos, Porcello, Price, Shark, etc. are available. Most of those guys are younger or can be had on shorter deals (Fister, Iwakuma).
Lester should be much better for the first 3 years of that contract, a time when the Cubs will still be on the rise but not ready to win it all. To me, it's not a very smart move to waste the first couple of years of Lester on a .500 team when you can sign younger and equal pitchers the following year. And Theo's much smarter than me, so I don't see the Cubs ultimately signing him. But I do see the Cubs PRETENDING to be interested to jack up the price on the Red Sox because Theo knows the Sox will be one of the bigger spenders over the next few years and one of his main competitors for FA pitchers.
NOTE: By pretending, I mean the Cubs would sign Lester if he comes cheap enough, but I think Theo wants to get the Sox or whomever to commit to that extra year because he knows it will help the Cubs in the long run by eliminating competition for FAs in the future.
Lester should be much better for the first 3 years of that contract, a time when the Cubs will still be on the rise but not ready to win it all. To me, it's not a very smart move to waste the first couple of years of Lester on a .500 team when you can sign younger and equal pitchers the following year. And Theo's much smarter than me, so I don't see the Cubs ultimately signing him. But I do see the Cubs PRETENDING to be interested to jack up the price on the Red Sox because Theo knows the Sox will be one of the bigger spenders over the next few years and one of his main competitors for FA pitchers.
NOTE: By pretending, I mean the Cubs would sign Lester if he comes cheap enough, but I think Theo wants to get the Sox or whomever to commit to that extra year because he knows it will help the Cubs in the long run by eliminating competition for FAs in the future.