I don't think this offseason is as complicated as some of you are making it out to be. For the Cubs front office, the real season starts in 2015. They really don't care what their record is in 2014. They have only 5 desires between now and Spring Training 2015: - find a manager who can teach, communicate and relate to a young and inexperienced nucleus - acquire top of the rotation capable arms - facilitate the process of their key minor league prospects (mostly hitting, some pitching) continuing to make significant progress - hope their key acquisitions playing in the big leagues today (e.g. Rizzo, Wood, Strop, Arietta, Grimm) each takes a solid step forward - land a top 10 draft pick in the 2015 draft As far as free agency goes, I don't think they see any long term solutions save for Tanaka, who they realize will in all likelihood be a Dodger, Angel, Ranger, Mariner, Red Sock or Yankee. The Daisuke experience is still fresh in Theo's mind, so I think their bid will be conservative. They will continue to hunt for flippable 1 or 2 year guys - the Scott Kazmirs, Chris Youngs, Nate McLouths and Josh Johnsons of the world. They could dip into catching if they get an offer they can't refuse for Castillo. They seem very happy with their prospects in terms of long term hitting potential. Their concern is #2 - pitching. And that's why I think this offseason is all about moving Samardzija, Castro, Schierholtz, Russell and even Castillo to get 2 or 3 top of the rotation ceiling guys, who are less than 2 years away. And supplement that group with excellent college pitchers, who they might find with their first round picks 2014 and 2015. It's fascinating to watch the build-up!