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Rival Exec Suggests Cole, Arrieta, Cueto, Estrada, Holland Could Be Among Cubs’ Targets This Winter

Chicago Cubs Rumors

From 2014-2016, the Chicago Cubs pitching staff recorded the third most WAR in all of baseball (behind just the Dodgers and Nationals).


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With very little turnover heading into 2017 and plenty of accumulated depth at the back end (Brett Anderson, Eddie Butler, Mike Montgomery, Alec Mills, to name a handful), there was little reason to believe they would take much of a step back this year, either.

Alas, after more than 50 games, the Cubs starting rotation has just 4.8 fWAR between them, which is good for 17th best in baseball, but I digress.

But even if the Cubs staff were performing up to expectations, their needs beyond the season would persist. After all, the Cubs are scheduled to lose both Jake Arrieta and John Lackey to retirement/free agency (not to mention Brett Anderson, should he return to form), and it’s not like anyone has stepped up to claim the fifth spot in the order yet.

To that end, Jon Heyman has heard some rumblings from rival GMs about the possible direction the Cubs may go with their rotation after the season, and I thought it was worth a brief discussion.


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First up, Heyman’s heard that the Cubs could target free agents like Marco Estrada and/or Derek Holland. I know these two names are rarely mentioned when discussing the supposedly exciting and upcoming free agent pitching class, but remember, the top of the class has been crumbling since the start of the season.

Estrada’s had an up and down career, but did post his second 3-WAR season last year with the Blue Jays and is on his way to repeat this season, as well. The exciting numbers for Estrada this year include an elevated 27.2 K% and a diminished 6.3 BB%. But while it’s great to see huge improvements like that, it’s fair to wonder if those sort of jumps are sustainable. Estrada is also about to turn 34.

(Photo by Greg Fiume/Getty Images)

Derek Holland is currently pitching on the South Side of the city, and has impressed with a 2.37 ERA … but his 4.37 FIP does little to inspire, and his 2.17 K/BB ratio does even less. I don’t want to dismiss him altogether, but his ground ball rate, BABIP, and HR/FB ratio are all down, while his strand rate is actually up. If anyone was due for some negative regression, it’s Holland.


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Things to get much more interesting beyond those guys, though.

For one, Heyman hears that the Cubs haven’t ultimately ruled out a return for Jake Arrieta, and, to be sure, if he continues pitching without high-end success, that becomes all the more likely. But we’ve discussed this possibility to death, so I’ll leave it here for now.

The other potential free agent Heyman mentions is Johnny Cueto, but as we pointed out earlier, he may not even elect to exercise his opt out if he doesn’t start pitching better and soon. Even still, Heyman points out that the Cubs “took a look” at Cueto before he signed with the Giants and if they thought there was value to be had there, they would not shy away. Cueto is just 31 years old, but his new contract would likely have to beat the four years and $90ish million he has left on his deal already. Would you go there?


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And finally, the last, but perhaps most interesting, option mentioned by Heyman is a trade for Gerrit Cole. The road blocks here are obvious – would the Pirates trade in the division, will Cole be dealt at the deadline or in the offseason, etc… – but the upside is pretty obvious. Despite a disappointing season last year (2.5 fWAR) and a relatively slow start this year, Cole, 26, is someone you want in your rotation, no questions asked. But again, would the Pirates be willing to do such a move? Would the Cubs want to help restock the Pirates?

Part of me thinks it’s possible, because the Pirates value young cost controlled position players as much, if not more, than any other team in baseball (given their financial limitations). So to that end, the fit with the Cubs could be ideal. However, there’s always the divisional up-charge standing in the way, so finding the right balance may be too much to overcome. We’ll have to wait and see.

The Cubs should consider themselves fortunate, though. Not many teams with three vacancies in their rotation will be met by a free agent/trade class that is so ripe with potential arms. In many years, they might’ve been forced to overpay just to fill their rotation with passable starters. This offseason, however, it seems they’ll have their pick from a wide field. No one can guarantee it’ll work out, but you’d much rather have more choices than fewer.


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Michael Cerami

Michael Cerami is a Writer at Bleacher Nation, and you can find him on Twitter at @Michael_Cerami.