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Kyle Schwarber
Arguably a Cubs legend already, Schwarber is an exciting slugger who has 40-homer potential written all over him. Although he’s batting leadoff right now, he could end up being an impact middle-of-the-order hitter for someone.
Pros: Being that he’s got so little experience, an extension could come cheaper right now than down the road. If Schwarber does end up reaching huge home run totals, then he may get too expensive.
Cons: Defensively he still needs work, and while he did make an unbelievable catch earlier this week there’s no defintiive spot for him yet. He could also very well end up being traded if a need arises, so waiting may be best before extending him.