Cubs Get Their Man – Sign Jon Lester to 6 Year, $155 Million Deal

Posted on 10 December 2014 by Lou

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Finally, late last night the Cubs got the news they wanted.  Free agent lefty Jon Lester had decided to go with the Cubs.  Theo & Co. set their sights on Lester whom they knew so well from their days in Boston and they did what it took to convince that Lester that is was now his time to help lead a young Cubs squad to the promised land – a World Series Championship.  Lester was a “young pup” in the Red Sox organization when new GM Theo Epstein helped the Red Sox break the curse with an improbable 2004 World Series title over the St. Louis Cardinals.  And just a few short years later, Lester led the Red Sox to a 2nd World Series title in 2007 with a sweep of the Colorado Rockies in the Fall Classic.  And he won a 2nd World Series ring just 2 years ago with the Red Sox.  Now it’s his turn to help the Chicago Cubs break their 100+ year curse.  How sweet it would be to do it with his friends Theo Epstein and Jed Hoyer at the helm.

Sure the $155 million had a lot to do with signing with the Cubs.  But Lester is an analytical guy and he wanted to make sure that Theo & Co. had a clear plan for the organization as a whole.  It didn’t hurt that the Cubs hired Joe Maddon just 1 month ago.  It didn’t hurt that he already knew players within the Cubs organization – he and Ryan Dempster bonded during their short time together in Boston and Dempster just joined the Cubs front office; Jason Hammel just signed a 2-year deal with the Cubs and he and Lester were teammates on the A’s during the 2nd half of 2014; and David Ross (his “personal catcher” with the Red Sox) has had talks with Theo & Co. about joining the Cubs as a backup.  Beyond that, the Cubs went out and upgraded their catcher position with a trade for Miguel Montero hours before they learned that Lester had made his decision to come to the north side.  It didn’t hurt that Lester knows that Theo & Co. are straight shooters who have won before.  And it didn’t hurt that Theo & Co. could also sell Lester on how great Chicago is.  They had long ties with the Boston area and it probably wasn’t an easy decision for them to leave 3 years ago.  But they did and they have embraced Cubs fans, the city and all it has to offer.  And they could make that clear to Lester — personally being able to tell him that sure Chicago was different than Boston, but it was just as good, if not better.

It was a perfect match.  The Cubs loved that at 30, Lester just had his best career year — 16-11 overall, 2.45 ERA with a 1.10 WHIP.  Even better than that, the Cubs know he can perform in the post-season.  In 14 appearances, Lester is 6-4 with a crazy good 2.57 ERA.  It gets even better looking at his World Series numbers — 3-0 with a 0.43 ERA.

We will definitely write more about the moves over the next few days.  So much to digest, and all signs point to the Cubs remaining active this off-season tweaking the roster here and there leading up to Spring Training.  After missing out on Russell Martin, this was huge for the Cubs to get their #1 free agent target.  What a day it was – checking twitter every few seconds, debunking false rumors, hoping Lester would pick us… And the he did.

We really wish it was Easter Sunday Night 2015 already — Joe Maddon coming out of the dugout with his 1st regular season Cubs lineup card — Jon Lester standing on the top step of the dugout getting ready to grab the ball for his start in a Cubs uniform at the Friendly Confines — the Cubs beating their hated rival St. Louis Cardinals and the Blue W Flag flying atop the new constructed outfield bleachers…  Can’t help imagining that same scene on a cool fall night in late October — Go Cubs Go!!!

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