Looking ahead to the upcoming trade season the Cubs obviously have several, relatively valuable pieces they can and will move. According to the front office and based upon the current state of the farm system, the Cubs will be targeting near-ready impact pitching.
However, I wish they would keep their draft strategy of taking the best player available not just trading for position of need. I know you can't always have this mentality, but it seems the cubs have been and will continue to struggle at least as much, if not more, on offense than pitching.
Also, the front office has done a good job at proving that they can identify the right pitchers to go after in free agency/trades - sans Jackson (though as we know, adv. metrics say differently). For example, Grilli, Sanchez, and Darvish were good targets; and obtaining Maholm, Feldman, and Travis Wood has proven fruitful. Couple this with the possible success of Baker and Vizcaino and its safe to say they have a good eye and ability to target the right pitchers.
Given that our rotation will likely be anchored by Wood, Samardzija, and Jackson next year, I rather see the FO go after the biggest possible impact player in trades this July while relying on off season free agency or trades to fill out the rotation. This also makes the cubs a better match with more teams looking for pitching this July which can, ideally, create more competition and thus a bigger return.