You're the GM of the Cubs this off-season. Here are the rules.
1. Money is not a problem. We have several revenue streams we will be cashing in this winter.
(Be within reason; we are not signing Price, Grienke, and Cueto)
2. Don't be "trade stupid"
(Oakland is not trading us Sonny Gray for CJ Edwards for Kyle Hendricks - TRY to be realistic)
What do you try to do with this 25 man heading into Opening Day next season?
The cubs have several ares of need. They are fine at C with Ross/Montero signed and Schwarber at C/LF mix. They are losing Herrera but with Alcantara in AAA and Baez already trying to find playing time I don't really see the infield as a big deal either. OF is a bit of a problem area. I believe Deno and Fowler are both FAs. Assuming they bring Cogs back in arbitration you need a #5 OF and a starting CF. Between Alcantara and Szczur they should be able to piece together a 5th OF on the cheap so I'm not that worried there. You could also find a ST invite guy to make the squad. But this topic clearly isn't about the #5 OF so who cares.
As for pitching, assuming they bring back wood they go 5 deep already with Rondon, Grimm, Ramirez, Strop, and Wood. Assuming you go with the traditional 12 man pitching staff you need 2 arms one of which being a lefty. In the starters, Harren is retiring and the #5 starter had something like a 4.50 ERA between all the guys they threw out there. Obvious problem area. Assuming Edwards sticks int he majors he can easily be one of the 2 missing BP arms. IIRC Richard is a lefty or perhaps I'm thinking of Cahill. Regardless you could bring either back or look for a lefty specialist to go with Wood.
So, that realistically leaves you two large FA needs being CF and a starter. With current salary commitments and probable arbitration the cubs are around $110 mil. I assume they will have around $30 mil more in payroll with signage, playoff revenue and tv ratings being up. The only two realistic options for CF are Span and Fowler. There's some talk of Heyward to the cubs but given he doesn't want to lead off and he's more a RF I don't think that makes a great deal of sense. I think Span will cost around $15 mil considering Rios got $11 mil to play a corner position for one year. I imagine Fowler costs around $20 mil. I don't really see any obvious trade options so it basically comes down to those two.
As for starters, there's 15-20 guys who are worth talking about which is a bit absurd. You should have around $15-20 mil to play with after making your choice in CF. It's kind of hard to realistically speculate on who will cost what. But the biggest thing for me is where is all the money going to come from for these starters? Typically speaking in a given offseason you have the top dog get <x> the #2 guy gets around <x - $5mil> and the #3 guy is around <x - $10 mil>. After that it's usually guys in the $15 mil range. I can see an argument made that the pitching is good enough this year that this model isn't going to be accurate. But if we assume Grienke and Price are the clear top 2 dogs, you still have Shark, Leake, Cueto, and Zimmermann behind them. And behind them you have guys like Lackey, Kazmir, Marco Estrada, Wei-Yin Chen, Yovani Gallardo, J.A. Happ, Brett Anderson and if he doesn't retire, A.J. Burnett.
As for starter trades, that's too difficult to speculate on. And honestly, I don't see that many trades happening because let's say you are San Diego for example with Tyson Ross/Cashner. Why would you deal either of them when you're looking at that many starters as FAs? Who's going to break the bank in terms of prospects when you can get a Lackey or a Kazmir maybe for $15 mil? My guess is the teams who might be looking to trade starters wait until the deadline next year to build value.
So, what would I do?
I think you re-sign Fowler. I don't really see any reason to screw with something that worked. But I also don't really think you can give him more than a 4 year deal. As such, I think you toss a QO on him which should hurt his value some and if someone gives him more than a 4 year deal let them have him and focus more on Span. If Span doesn't work out either, you have some options in re-signing Jackson, giving Szczur a whirl, giving Alcantara another shot or possibly playing Castro/Baez in CF though that is obviously not ideal.
As for the starter, Lackey makes a lot of sense to me on a 2-3 year deal. The cubs have some pitching it's just below AA. He provides a bridge to that. Obviously, if someone like Zimmermann goes for $15 mil over 4 years then you should jump on that instead but as I said I'm not 100% how the pitching market will develop. Basically, I'd get the best guy you can for a 4 year deal below $20 mil.
That takes care of the basic opening day roster. After opening day I think they will eye Pierce Johnson as a possible replacement in the rotation around the start of July if Hammel/Hendricks aren't pitching well. You could also eye a trade to improve the rotation at the deadline possibly including Hendricks/Hammel or Johnson as well as probably better prospects.
I also expect the cubs to make a few minor trades to move some rule 5 eligible players like Vogelbach because I'm not sure they will be able to fit them on the roster and let's face it, guys like Vogelbach, Corey Black, and Daury Torez probably don't figure into plans. Trading them for a young lefty reliever could make a lot of sense to strengthen the bullpen.
Some have also mentioned the idea of signing and trading for a second starter. I'm highly dubious on that. Only way I see that going down is if someone who's too good to pass up becomes available and you do a large trade. For me that would be someone like Julio Teheran or the aforementioned Gray but again I don't think that's likely. Some of the lessor names mentioned around the deadline like Tyson Ross and Carlos Carrasco I certainly wouldn't mind having but I just don't really see the Padres or Indians getting what they will want to move either given the FAs.