Off-day ruminations on feelings, plans and the future of the Chicago Cubs

An argument that keeps popping up essentially goes like this:

Poster A: The Cubs have their least-bad team since probably 2009 and the first wave of prospects is beginning to congregate in Iowa. This is exciting and the Plan is justified!

Poster B: The team is still awful and there's nothing to be that excited about, the Plan is a failure.

As is my tendency, I am happy to tell them both that they equally wrong. The team is much more bearable than it's been in awhile, the near future looks even more exciting, and the the Plan was never the best course of action. My objections to The Plan have never been "It won't ever work and we'll never have a good team again." My objections were "we're trading too many season to get to that point."

My standard for measuring organizational success has always been playoff appearances. It's a bit arbitrary, but I think it's justifiable. Raw win totals don't account for a front office's responsibility to gauge where the team is relative to its divisional rivals and add/drop accordingly. Pennants and rings place too much emphasis on getting lucky in the short-series coin flips that are postseason baseball. Boston's run of 6 postseasons in 7 years impressed me more than the fact that two of those appearances ended in a parade. They are now looking at missing for the fourth time in five years, and that paints a more accurate picture of the franchise to me than the fact that their one appearance resulted in a third title. If the Cubs never win a World Series under Epstein but make 11 playoffs in 15 years, then he did his job and then some.

My problem with the rebuild has always been that it puts you in too much of a hole. If the Cubs don't have a real miracle run in them in the next month, then we're looking at 0-for-3 on making the playoffs. If even a few things go wrong in 2015, then we're probably looking at 0-for-4. It's almost impossible to have more than a passingly respectable decade after a start like that. The only way you can pull off more is to go on a near-perfect run afterwards (which almost nobody can do in the current MLB environment) or be sure that the organization you put in place will carry over far beyond that decade (and I don't think anyone can try to plan around that. See the currently flailing Red Sox). In summary: I want sustained success, but it's not sustained success if you just lock in the losing at the beginning.

I am aware that some will say that the Cubs had no choice but to take those lost seasons, to which I say that there are far too many examples that say otherwise. Two off the top of my head: the 2011 A's (74 wins, 28th BA rankings, almost no payroll) or the 2013 Brewers (74 wins, No. 23 BA rankings, medium-sized payroll). Would aiming for those sorts of seasons have slowed down the ascent up the farm system rankings that we've seen? Sure, but good organizations will still produce a steady stream of talent in the long run. I hope that with all the emphasis we've put on player development, the farm system won't suddenly dry up the instant we stop drafting in the top 5 every year. If it does, then we've never even had a hope for sustained success, we've just been enacting our version of the classic small-market "Golden Generation" plan that we've seen the Brewers, Reds and Pirates enact in our own division.

OK, now that all that's out of the way, we can get to the fun stuff. How good could the 2015 Cubs be? As good as the front office wants them to be. Almost certainly not bad.

If we take it for granted that Jeff Samardzija is going to be traded, then imo this is the best 25-man roster we could reasonably construct for 2015 with players already under control:

Ruggiano($2.5#), Alcantara (PA), Bryant* (PA)
[Sweeney ($1.5), Lake (PA)]

Valbuena ($3#), Castro ($6), Baez* (PA), Rizzo ($5)
[Barney ($3.5#), Watkins (PA)]

Castillo ($2#) [Lopez (PA)]

Arrieta ($1.5#), Wood ($6#), Jackson ($11), Hendricks (PA), Grimm (PA)

Rondon (PA), Ramirez (PA), Strop ($2#), Vizcaino (PA), Rivero (PA), Russell ($3#), Wright ($2#)

Total cost: ~$56m

PA - Pre-arbitration, assumed to be $500k for simplicity's sake

* - Coming up in late April after the service-time deadline

# - Arbitration WAG

(There's a lot of ways you could tweak this roster and do different things with it. There are several perfectly reasonable candidates I left out of the bullpen, I'd rather not have to reconvert Grimm back to starting, you could definitely shuffle some of the positions around to make openings elsewhere.)

On a downward run for four straight years, the Cubs' payroll has gone all the way down to about $88m this year. Even if it were to lower a bit more, that's still a ton of room to work with. And I'd expect some non-tenders or salary dumps (Barney, Russell being obvious candidates) to lower it even more. All in all, that is a fairly impressive blank canvas for Epstein to work with, and given that he's been working on it for three years now, it should be.

But while it doesn't appear that payroll space will be a major impediment to the Cubs' improving this offseason, there are still two major roadblocks: the increasingly weak market for players and the Cubs' front office's reluctance to commit to long-term resources.

On the first roadblock, we've been saying for years that each year the market gets worse. The short explanation is that a combination of more aggressive revenue sharing and massive TV contracts have given previously cash-poor teams enough money to convince their developed talents to sign for long-term deals before reaching free agency. This same explanation is why it's becoming harder and harder to pick up salary-dump trades for current major leaguers.

On the second roadblock, I'm not even saying they are wrong. But a long-term deal is essentially selling out a bit of the future for the present. Sign a pitcher on a 4-year, $80m deal, and you are essentially eating away at the flexibility and projection for years 3 and 4 in exchange for a bump in years 1 and 2. I don't think this front office is willing to do that for the sake of the 2015 Cubs when they could easily wait one more year and have more of a sure bet on their hands in 2016. They didn't wait this long just to blow their wad a year early, imo. The only exception might be a younger guy like Maeda.

So while I expect us to be fairly busy this offseason, I don't expect us to be after the top tier of free agents, the Lesters and Scherzers, who will require 4-, 5- or even 6-year deals. I expect them to be hitting hard on the middle-tier, guys who are probably immediately useful major leaguers but whom will only be requiring 1- or 2-year commitments. We'll probably even be willing to pay a little extra to get that.

What sorts of targets? Well, I think we all know the answers by now. First, here's a back-of-the-napkin WAR projection for the above roster:

Ruggiano (1.0), Alcantara (2.0), Bryant* (3.0)
[Sweeney (0.5), Lake (0.5)]

Valbuena (2.0), Castro (3.5), Baez* (1.5), Rizzo (4.5)
[Barney (0), Watkins (0)]

Castillo (1.5) [Lopez (0)]

Arrieta (2.5), Wood (2.0), Jackson (1.5), Hendricks (0.5), Grimm (0)

Rondon , Ramirez , Strop , Vizcaino , Rivero , Russell , Wright (4.5)

Team WAR projection: 31 Projected record (48-win replacement level): 79-83

Now, I'll be the first to admit these WARs are pretty much WAGs, but it's a fun exercise. If someone wants to say that Castillo is clearly a 2.5 or Jackson clearly a 0.5, then I can't tell them they are crazy. I tend to be pretty conservative because these need to account for the chances that players just completely fall apart like 2012 Soto or 2013 Byrd or 2014 Sweeney. Bryant's is heavily based on Anthony Rizzo's 2012 season, which serves as a guide for what a young guy crushing Iowa can be expected to do in his first extended look at MLB pitching. Arrieta's would be a lot higher if I knew for sure he'd be throwing 30 starts, but I think he's got massive health red flags. The bullpen is easier to just do as a whole, and a 4.5-WAR bullpen is above-average but not elite.

So what can we do to improve on this? The most glaring need is starting pitching. I'm a big believer in accounting for the high-risk nature of pitching. While the bullpen has plenty, the rotation is woefully thin. I don't really want to re-convert Grimm or anyone else, so I'd say we have at most four guys I'd be comfortable with entering the season in the rotation, and most years I'd want that number to be seven or eight. We need to be getting least three such pitchers between the upcoming trade deadline and the offseason. The front office has been proactive on this front in the past, so I expect them to handle this problem. I don't think we're going to be able to find a front-line guy, and that will undoubtedly be our biggest weakness, but it's not one that disqualifies you from contention immediately. Keeping Samardzija would be a coup in this regard, but that's a whole other conversation.

The position player needs are bit more fungible. You need at least one outfielder for sure. You need to improve your infield depth, which you can do by either signing veteran reserves or by signing a second outfielder and keeping either Alcantara or Bryant in the infield, pushing Valbuena back to the sub role. I'd really like to see them spend some money on a veteran, reasonably reliable catcher to at least complement Castillo or maybe even put him in a backup role.

So our shopping list for the trade deadline and the offseason comes out to: Three starting pitchers, two position players (at least one an outfielder), and a veteran catcher. That would give you perhaps the following team:

Free Agent (2.0), Alcantara (2.0), Bryant* (3.0)
[Ruggiano (1.0), Sweeney(0.5)]

Valbuena (2.0), Castro (3.5), Baez* (1.5), Rizzo (4.5)
[Free Agent (1), Watkins (0)]

Castillo (1.5) [Free Agent (0.5)]

Arrieta (2.5), Free Agent (2.5) Wood (2.0), Jackson (1.5), Trade Return (1.0)

Rondon , Ramirez , Strop , Vizcaino , Rivero , Russell , Wright (4.5)

Team WAR projection: 37 Projected record (48-win replacement level): 85-77

That team is still a tiny bit light in the infield, but otherwise I really like the depth. Guys like Lake, Hendricks, Grimm, Parker, Rosscup will have a good case for making the roster and there will be plenty of the tough spring decisions that good teams should have to make. Probably (as in less than 50%) not a playoff team, but you've kept your payroll flexibility at insane levels, given your first wave a chance to get acclimated to baseball, and finally pulled yourself out of six years of baseball hell.

tl;dr: We're going to be good soon, plan still sucks, future is exciting.

This is a FanPost and does not necessarily reflect the views of SB Nation or Al Yellon, managing editor (unless it's a FanPost posted by Al). FanPost opinions are valued expressions of opinion by passionate and knowledgeable baseball fans.

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