Feel free to chime in with votes and comments now, and over the next 24 hours I'll put together my own take.
It's the Cubs. They have the better farm system and better young talent overall. They also have contracts which will set to expire at the end of the year that will leave them with money to spend.
The Sox meanwhile have become baseball's biggest short term thinking team. They have consistently dealt prospects (i.e. Gio Gonzalez, Daniel Hudson, Chris Young) for short term fixes. There farm system is in ruins. When their contracts have to expire they're going to have to spend again on the market since they have little depth (apart from starting pitching, possibly) from which to trade. And the Sox haven't historically been an enticing destination for top free agents, so even there ability to land free agents is a question mark.
The Cubs, while being the inferior team this year, at least have some semblance of long term planning and direction. The Sox seem to be playing by ear.
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