Jon Lester signs with Cubs, Fans Fear How This Will End

Jon Lester Chicago Cubs MLB 2014 Free AgencyI’m a life-long fan of the Chicago Cubs. I’ve been through it all. I was born in 1980 and one of my earliest baseball memories was the Cubs’ 1984 playoff collapse. I dealt with numerous inept managers, a handful of ‘this is our year’ years and the whole Steve Bartman ordeal. The Cubs now have a stockpile of blue-chip prospects, but nearly all are position players. Chicago needs quality pitching and they just signed the biggest name this offseason.

Jon Lester, formerly of Boston and Oakland, signed a six-year $155 million dollar deal (with an option for a seventh year).

Theo Epstein and recently-named assistant Ryan Dempster both have a relationship with Lester. It gave them a much-needed edge.

I breakdown this signing and a few other ramblings about the upcoming Chicago Cubs season. Also, gaze upon my awesomely horrible MS Paint skills.

The Cubs now have a starting rotation of Jon Lester, Jake Arrieta, Travis Wood, Edwin Jackson and Tsuyoshi Wada. Kyle Hendricks and C.J. Edwards (eventually) could both end up in the starting rotation. Chicago could benefit from dumping both Wood and Jackson. Hendricks and Wada both out-pitched them last season. They are also rumored to be after at least one more top-of-the-rotation arm.

The Cubs reportedly out-bid the Red Sox by nearly $20 million dollars. Boston’s low-ball offer last offseason could have soured negotiations this offseason. Chicago is currently in a better situation going forward. Boston’s prospects have been failing left and right. They will need to overspend to contend in the AL East.

Chicago also traded for Miguel Montero, since they don’t have an MLB-ready catching prospect. They are expected to shop Wellington Castillo and should get something decent in return. The Cubs are also looking at free agent backup catcher David Ross, who has many interested teams.

It’s way too early to throw Chicago’s name in the World Series contender discussion. They jumped to 12 to 1 odds of winning the World Series. Cubs fans do have a lot to be excited about. Their farm system is loaded with elite hitting prospects, but their track record of developing homegrown talent is very poor.

Cubs fans are naturally pessimistic and signing Lester brings us joy and fear. We can all enjoy today and let’s worry about the eventual letdown when it comes. Mazel tov!

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sweetbob-author-picAbout the Author…

Bobby Roberts (otherwise known as Sweetbob) is the creator of ‘America’s White Boy’ and contributor at Project Shanks. His writing has been featured on ESPN’s ‘SportsNation’, Sports Illustrated’s Hot ClicksGuyspeed, and various other sites. You can follow him on Twitter at @Sweetbob.

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