When should the Chicago Cubs start holding on to good pitching?

The last few seasons have seen the Chicago Cubs acquire pitching in the off-season with low risk/high reward payoff come the next years trade deadline. Since the Cubs were clearly in a rebuilding state, it’s been completely logical. Paul Maholm and Scott Feldman. Now Jason Hammel and possibly Jeff Samardzija. But when do the Cubs need to say it’s time to hold on to some of these arms? I think that time is sooner than later.

It’s no secret the Cubs farm system is much improved under the new front office. With names like Javier Baez and Kris Bryant among others, the future is bright. When this group of prospects hits Wrigley is still up in the air as the organization is treading carefully with all of them, giving them time to progress and grow within the system.

But eventually the Cubs are going to have to look at balancing that “trade value” of all these pitchers with keeping the current roster competitive. Chris Bosio has done a spectacular job with the pitching staff. There’s no question the Cubs have potential on this staff. But with contracts about to run out, the talk is to get as much as they can for these guys while they can.

But then what?

Trading these guys at mid-season will be for basically two reasons. First, someone is in dire need of pitching for a playoff push. In turn you’re going to get mid-level guys, and likely not pitching, which is what we need. Or you just want to unload a guy because you don’t feel you’ll be able to re-sign them and want to get what you can. That can lead to not getting proper value for a player.

I’m aware the Cubs can’t keep all these guys, and many people feel very strongly one way or the other. “We’re still three years out, trade them.” Or, my thought, these are the guys we will be looking for in a few seasons and we’ll overpay for them. Samardzija is becoming a number one or two starter without a doubt. Travis Wood is probably a #2, and Hammel a #3. But these are all quality guys that aren’t past their prime. What are they going to do, ink another pitcher like Edwin Jackson in three years? (In his defense, he’s been much improved this season, but still WAY overpaid.)

No, the Cubs aren’t “there” yet. But I feel like with every trade like the ones being talked about, we reset the rebuilding clock a year or two. We aren’t pitching rich in the system. We have to start assessing need and saying, “Okay, we’ve got a good arm, let’s get a deal done.”

But I can’t sign them, I can just write about it.

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