Lester floundered a bit in 2012, at least ERA wise, and had a nice bounce back in 2013 before conveniently posting his career year this season, just in time for his free agency. That's not to say that Lester isn't the real deal because he is and he just earned himself a boatload of cash. Even in Lester's down year he put up 3.2 WAR, which in today's baseball economy could be a $20 million pitcher. That's the low end of a healthy Lester, which is certainly no guarantee for any pitcher but it shows you how consistently solid Lester has been in his career.
Max Scherzer puts up gaudier strikeout numbers and is expected to make more money than Lester during but production wise they are very similar. Considering that Scherzer is looking for $200 million, Lester's contract in comparison might end up a bit of a bargain.
There were rumors during the season that the Sox offered Lester a four-year $70 million extension. Lester appropriately declined and ended up being shipped to Oakland for a year of Yoenis Cespedes. I'm not entirely sure what was offered and what was said but since we now know that Lester will be making more than double the initial Red Sox amount, that's the definition of a low-ball offer. It's hard to say it had an affect on the current negotiations as Lester was still considering Boston, but chances are the Red Sox could have had Lester at whatever price they offered this time, if they only offered it in the summer.
Either way, Lester is now a Cub and the Cubs are now ready to compete for the playoffs, division titles and the World Series, maybe even as early as 2015. Jon Lester and Jake Arrieta make a very formidable front end of the rotation and if Theo has taught us anything it's that he's very capable at filling out the rotation with solid pieces. Behind the big two are Jason Hammel, Travis Wood and Kyle Hendricks with Edwin Jackson and his contract lingering somewhere.
The previous talk about the Cubs was always about their young hitters and the "need" to swap a young bat for a pitcher. Well, I'm not sold that ever was the case, and it certainly isn't now. The Cubs have three solid starting pitchers and Theo isn't going to trade a young bat to fill out a rotation in the National League as he can do that on the scrap heap in his sleep. In fact, if the Cubs have any holes it's in the field. Third base and left field are currently being filled by Luis Valbuena and Chris Coghlan/Junior Lake but there is someone named Kris Bryant that can and will fill in one of those slots before the summer. The Cubs lineup isn't particularly good right now but given the ages of their core, it should only improve.
Smarter people than me, like Dave Cameron can tell you more specifically why the Cubs are contenders now, so I'll just lead you there if you don't believe me.
For baseball fans this is exciting because Lester is the first truly compelling domino to fall this offseason. Now we get to watch the Hot Stove heat up with Max Scherzer and trade rumors for those teams who missed out on Lester.