I was one of the leaders of the "Trade Starlin" movement two years ago.
To this day, I think there were good reasons to do so. I am a believer in having the strongest defensive shortstop possible at the position. Castro has worked hard and become average to slightly above average but that is his ceiling. I also didn't think he would ever become a patient hitter. There are mixed results on that. While the walk rate is up, it's still nothing to write home about at 6.2% and that's come with higher strikeouts (17.2%) and a lower batting average than in his early years. However, his ISO of .164 is the highest of his career by 17 points and he still seems to be growing into his power.
How do the changes shake out? If you look at Starlin's wOBA -- a good "catch all" offensive statistic -- it's currently sitting at .335. 3 points lower than it was in 2011 before he was "fixed." If you want to take an optimistic viewpoint, you can argue that the changes to his swing make it more likely that his offensive production will increase as he grows into his power. If you want to be more cynical, you could say that the Cubs went through an awful lot of trouble to get the exact same offensive production out of Castro at the end of the day as they had going in.
Having said all that, when I hear calls to trade Castro as soon as this offseason for young pitching (a Mets package including Zach Wheeler and Noah Syndergaard being the most popular), it makes me more than a little uneasy.
We have all seen the plan coming together and putting this team right on the verge of being relevant. Rizzo and Castro have emerged from their cocoons (also known as the 2013 season) and both earned -- and I truly mean earned -- their place on the All Star squad. Alcantara gives the offense a dynamic catalyst at the top of the order and big, middle of the order bashers Javier Baez, Kris Bryant, and Jorge Soler appear to be on the verge of Wrigley. The bullpen is almost unrecognizable and the free cash resources should bring in the pitching currently lacking at the minor league level.
The timeline to be competitive changes if we trade him this winter. We would be getting rid of a guy who has already gone through major league growing pains and can be counted on to deliver consistent, above average (indeed, All Star level) production right now. How good has he been? His .335 wOBA (John's favorite offensive stat) makes him the 4th best shortstop in the league. If you look at RE24 (my favorite stat for looking at past offensive performance), his 8.34 ranks him 5th in the league. With the Cubs on the verge of being relevant, and perhaps 2 years from Juggernaut status, getting rid of the 4th or 5th best offensive shortstop in the game for guys who may or may not contribute meaningfully at the major league level is a bad idea.
I can foresee a time when it might make sense to trade him. When our prospects have graduated, and we're lucky enough that Bryant, Baez, Russell, Soler, and Alcantara have all become offensive contributors that equal or exceed Castro, then it makes sense to trade him to open up space. But that is a long way, and a lot of luck, in the future. Even if you think (as I do) that Addison Russell will be the starting shortstop in 2017, if Baez and Alcantara (for example) don't fully make the adjustment to the majors, the team can still extract a lot of value from Castro by simply sliding him over to second base.
We are on the verge of competing. We have a legitimate offensive weapon in Starlin Castro. Unlike Samardzija, if we do nothing and pick up his option he will be a Cub for six more full seasons. This is a guy who we can ride, cost controlled, through multiple playoff runs. He has some holes in his game, but this is exactly the wrong time to make the perfect the enemy of the good. Sign me up for six more years of an infielder who will hit .270 to .290 with 20+ home runs.
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