Not that the Cubs have been eliminated from the postseason, it's time to look towards 2016. This will be a short post on some of the relevant things.
Should the Cubs re-sign Dexter Fowler?
Here are dmick's thoughts on this issue. I'd just extend a QO to him, expect him to decline it, and reap the 1st round pick reward (for those keeping score, Jed claimed Luis Valbuena off waivers, spun him for a Top 15 CF, and will soon get a first round pick for his troubles). The Cubs don't lack for hitting, and Fowler at 30-34 doesn't figure to be in the Cubs' plans.
What holes do the Cubs have?
To figure out the holes, let's figure out where we're set. Russell and Rizzo are for sure staying at SS and 1B. Schwarber and Soler will likely be at the corners unless Bryant ends up there, which moves Schwarber into backup-catcher duty or Soler to the bench (and likely another team). Bryant could start at 3B, LF, even CF! I think he'll end up at 3B for now. Either Baez or Castro will be the 2B: Baez could start learning CF but I don't think that'll happen. I assume one of the two are on the outs with this team. Montero and Ross are the catchers next year, for better or worse.
That leaves CF and the backup outfielders, and probably a backup infielder or two depending on if you want to use Baez as a supersub. Denorfia is gone and probably won't be resigned; Coghlan is probably the backup 2B/COF once Baez or Castro is traded. I think the Alcantara ship has probably sailed; he showed essentially no improvement, scouting or otherwise, in AAA last year. Holding onto Herrera wouldn't be the worst thing in the world.
UTIL: La Stella
Outside the org: Castro
I like Starlin Castro. I think he can be a nice player for a long time in the league. It's not even a guarantee that Castro is gone- it could be Baez or neither. It does seem, however, that we're at the point where someone must go to realize their whole value. There just isn't a neat permutation where everyone fits without putting someone in CF who probably will struggle there (especially when your outfield defense figures to be below average anyway).
I think your OF search has to begin with a long look at Jason Heyward. Heyward puts up 120 wRC+ like clockwork. His approach at the plate is exactly what the Cubs want: low strikeouts, high walks, works counts, has enough pop where you can't challenge him too much. The two issues are cost and fit: he'll cost too much and he hasn't played CF predominantly essentially since the day he reached the majors. You have to do some diligence with Heyward simply because he's the best FA hitter on the market, but I don't think the Cubs should (or will) be major players for his services.
Next, I think the Cubs will look at Dexter Fowler. Fowler is very good, and he's familiar with the team. He sets the table nicely and is a good clubhouse guy. That said, I think he'll be too expensive for the Cubs, especially at the end of his (presumably lucrative) contract. The market could be unexpectedly shallow considering the recent history of guys with vaguely similar profiles (Melvin Upton, Michael Bourn). That's unfair to Fowler (a better player than either), but if that sets his market at 5/60 or something like that, a) he might take the QO and b) you might be ok with that that.
Following Fowler on the list is Colby Rasmus. I've long been a Rasmus fan, almost entirely because Tony La Russa hates him (dying laughing). He has lots of flaws ("elevated" strikeout rates, increasingly poor centerfield defense), but he also walks and hits home runs. Only Mike Trout, Adam Jones, and Andrew McCutchen have hit more HR over the last 3 years while playing primarily centerfield. Rasmus signed for 1/$8 last year and wasn't so much better this year that you'd have pay a ton more than that. If Rasmus would sign for something like 1/$11 with an option somewhere in there (this seems reasonable, as the Jays are certainly not extending a $15.8 MM QO for fear of acceptance), the Cubs should look long and hard about that. I wouldn't go super long-term for him; if you were in the market for a long-term bat, you might as well keep Fowler.
Denard Span is a special case. He was on pace to be a very attractive option until he was injured. The combination of the QO he'll likely receive (and likely reject) and the uncertainy surround his health means the Cubs will likely stay away.
Last on the list is the Austin Jackson. I don't love this option, as Jackson profiles better as a 4th OF at this point. That being said, he plays well above-average CF defense, which isn't nothing, and he'll be cheap, which isn't nothing either. Something like 1/$6 probably gets him, and holds you over until next year when maybe Almora or someone else on the team takes over.
There are a million 5th OF options out there and it's total foolishness to try and guess who it'll be. It could be Denorfia, or anyone of 1000 different ST invitees.
On the pitching side, it's a lot murkier. The Cubs have 2 bonafide starters next year in Arrieta in Lester. After that, I'd look to bring in at least 1 and probably 2 strong pitchers for the rotation. Hammel and Hendricks are nice pitchers to have competing for a #4 or #5 spot, but they shouldn't be guaranteed spots on the rotation.
The top tier for starting pitching is huge. Johnny Cueto, David Price, Jordan Zimmerman, and Zack Greinke will all command huge contracts, and the Cubs will be in on all of them. only Zimmerman will require forfeiting a 1st rounder for.
The next tier of starting pitching is still plenty intriguing. Jeff Samardzija is a year removed from turning down a 5/$75 offer from the Cubs (reportedly) and being traded for our SS of the future. If he received that offer from any team, including one in a Cuban League, you'd think he'd have to take it. He should sign for less, perhaps even a one-year pillow contract with the White Sox (taking the QO if they offer it). Mike Leake is a #4 pitcher incarnate; he throws 190 innings, is right around league average, and will cost $12 MM a year for 3 or 4 years. That's probably fine, but I could be way off. Mat Latos is reportedly an asshole who looks like several bees have always just stung his face. That said, until last year he was extremely good. His strikeouts fell off the cliff in 2014 when he was injured; he's never been the same since. Latos is exactly the type of player that gets a ST invite with a $4-6 MM split contract, and it might be with the Cubs. Hopefully not. Scott Kazmir has been really good in the first half of each of the last two seasons, and not as good in the second half of the last two seasons. Maddon managed Kaz for 4 years in Tampa, and seems a natural fit to come over here. I wouldn't be surprised in the slightest if Kazmir ends up a Cub this offseason.
There are others that I'm probably missing, but that seems like the major players in the rotation. I hope the Cubs get 2 or even 3 of these guys.
In the bullpen, only Rodney and Motte are gone as far as players of any consequence. I think Rondon/Strop/Wood/Cahill/Grimm are good bets to stay in the bullpen, and they'll look outside the organization or in the minors to fill out the rest.If Neil Ramirez is healthy, he's in there too. I could see the Cubs breaking camp with those 6 + Carl Edwards Jr. + a mid-tier reliever signing (probably a lefty) like Manny Parra.
The Cubs spent $133 MM on the roster this year. After all the predicted arb raises, this year's payroll is already at $127.3 MM (the Cubs aren't picking up Cahill's option, but they might re-sign him for something like $4 MM). That means the Cubs probably only have $22 MM or so to play with. If the Cubs trade Castro, it becomes $30 MM (if they trade Baez, it stays $22 MM but they likely have one less rotation spot to fill.) Let's assume that neither happens; it's always icky predicting a trade. I could easily see an offseason that goes:
Re-sign Austin Jackson (1/$6)
Sign Scott Kazmir (3/$45)
Sign 2-3 random starting pitching fliers
Cubs fans should brace for an offseason that isn't overly exciting; the money isn't there until next year, when the EJax and Hammel contracts come off the books (and free up $20 MM). Without knowing how much the Cubs are willing to spend, it's a fool's errand to predict this with any more precision.
Watch the Cubs make me look stupid.