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5. Brendon Little
A former 1st round draft pick in 2017, Brendon Little has been struggling to find his footing in the system for a while now. Formerly ranked as the organization's sixth-best prospect, the Cubs were expecting him to at least be a big-league contributor at this point. But the left-handed pitcher put up a less-than-desirable 4.29 ERA last year in 50 innings of relief at Triple-A. At 26 years old, time is running out for Little in the now pitcher-heavy Cubs system. As a southpaw, his talents could be useful at the big-league level if he can find himself again.