I would have preferred trading (the tradeable) Upton and trying to sign Heyward. Maybe hasn't lived up to potential but still quite young. Upton strikes out too much for my taste and his defense has either gotten a lot worse or was way over rated he is pretty bad in LF and his brother isn't exactly a good CF these days either but we are stuck with him.
Understood your point about it being more from Cubs perspective. I've read that trading Castro now seems more likely. I think he is pretty good though maybe off field problems are part of the reason they would move him.
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