1 - What's their profile of a CF? Jackson probably lags behind defensively what they want if that's what you're thinking, and I can agree with that. That said, they have very rangy OF guys with Jennings out there in LF and possibly Guyer out there in RF next year. 2 - The answer to your question is that trading Jackson does not make or break that ultra vague "build from within" plan, Jackson is pretty mid-range for a top prospect, and there are alot of guys who came from within the farm system that are now useable players here. Soto, Barney, the bullpen, and then one of the best young SSs in baseball sounds like within to me. It's such a vague and general description that it's possible to include trading away Cubs' prospects and players for better players when possible in the "build from within" category, isn't it? It's using what they have already to get what they don't have but want. Despite Tampa's supposed MO under Friedman, they are one of the more toolsy organizations in MLB. Jackson isn't athletic enough for what they look for in a CF. Joyce will out there in RF. The Cubs are in a rebuilding mode and while Tampa could very well unload Upton one year early rather than one year late, I still wonder why the Cubs would want to trade for another CF'er beyond valuing Upton more than Jackson (which on the surface, makes sense as Jackson likely won't duplicate Upton's ceiling). That includes factoring some of Upton's numbers falling short of expectations. CFs are allowed to play corner OF positions, too- it happens pretty often now Thanks for the update, you blew my mind with that one. Jackson's value drops considerably putting him on the corners.