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Derek Holland
There’s a reason that you find so many White Sox starters on this list. The team is in full blown sell mode, so everything must go. Derek Holland is one that the Cubs had on their radar years ago, but nothing ever materialized of it. Injuries have plagued him, but if anything he’s been able to go out and take the ball every fifth day. The results every fifth day have been less than impressive.
The one place that he does excel is against lefties. With a slash of .216/.279/.333 in 2017, he could be a solid LOOGY out of the bullpen. The Cubs already have Brian Duensing who has fared well in that spot, and Mike Montgomery could fall back into that role once Lester returns.
Holland’s “hey day” has passed, and at this point, he’s not going to serve the Cubs well in his current role. Of the starters on this list, he fits the least of any of them for what they’re looking for.