I know we talk about "windows", but at this point I think Theo should also be thinking about how he can extend this window in perpetuity and become an organization like the Cardinals, Dodgers, Yankees, or Red Sox who are in contention every single year. I'm not interested in the Cubs selling out for a five year window where they win one or two and go back to historical suckage again. I want this organization to be one that is competing for playoffs every single year and, when the stars line up or the team gets hot, you get a shot to win it all. The Cubs are a big market club and have the resources where this should be possible.
Point is, I'm keeping the depth and the future in Happ and Russell rather than sending them off for DeGrom. We would have an ace on the staff if Yu would ever take the hill again. If Yu is healthy and having the season he is being paid to have we aren't talking about trading assets like we are right now. We could get DeGrom and he could suffer "stiffness in his shoulder" 3 starts into his Cub career and now you've divested assets for yet another DL superstar. Pitchers are to injury prone.
I don't disagree with the injury concern....and yet you need pitching in the post-season, so it's always a gamble.
As for the talk of windows, the ability of Theo to extend the window is going to mean specifically that they don't keep all these kids. The good and the bad of this current wave of Cub talent is that the team was so bad prior to the kids that they really all came up around the same time....which means their free agent years will all hit around the same time, which is also right there with the end of Jon Lester's and Anthony Rizzo's contracts. You're not just going to keep them all for ever.
So, there is this arbitrary 5-year windows just because of who is cost controlled and who is under contract. If you can flip a couple of these guys for players maybe better able to help win now, you not only increase the chances of winning now, but you create an opportunity in your organization. There is another wave of talent coming and by 2019-2021, there will be places to put the kids that emerge.
At the same time, the Cubs are going to have to pick who they pay and keep for the longer haul. It won't be all of them. Look at Schwarber, Happ, Almora, Baez, Russell, Rizzo, Bryant, Contreras, Lester, Zobrist who will all hit FA in 2020-2022. Lester and Zobrist will either retire, walk or take smaller contracts, so they won't be major factors at the ends of their careers. Rizzo might be in line for one more good payday, but I can't see the Cubs giving him many years. Out of the rest, a couple probably won't progress to the point where they'd be major FAs, but a couple will get some paydays. How many does it make sense to keep?
Of course, I'm not talking about dumping guys, but some organizational churn is a good thing because you really don't typically want a wave of young players that all come up together and then get expensive at the same time. Ideally, the Cubs would be rolling a couple decent kids in every year or two. That let's you do a lot of things and lets you take a run at some really interesting trade options. I did not intend my post to be read as "gut the system and do all things necessary to win in this 5 years"...it's just that moving some of these guys is a healthy thing.