I know I sound like a broken record when I make posts like this, but I saw Charlie's post tonight about "punting" and since I've been wanting to build on my own post from ten days ago on the same subject, this seems like a good chance.
The Pirates are at a crossroads right now. When Neal Huntington took over after the 2007 season, the Pirates were in bad shape and headed for disaster. The whole franchise was funnelling into a Major League team that wasn't very good and was scheduled for demolition after the 2009 season. There wasn't much high-pedigree talent behind Andrew McCutchen in the minors: the first round picks after him were Neil Walker, who was stagnating at the time, Brad Lincoln, who was out with Tommy John surgery, and Danny Moskos, who wasn't a good prospect on the day he was drafted. Because McCutchen's arrival was going to approximately co-incide with the departure of pretty much everyone on the big league roster, Huntington's job on day one had two components: try to scrap something together to build around McCutchen in 2010 and try lay a foundation for the longer-term future.
At that point, pretty much everything involving the team's present could be compromised in favor of those two goals. The Pirates weren't going to contend in 2008 or 2009. Trade Nate McLouth out of the blue? Fine. Trade Jason Bay more than a year before he hit free agency? Go for it. Trade Nyjer Morgan the second he shows a shred of value? Make the phone call. Huntington probably made a good read on the timing of each of those trades (you can argue about the returns in each deal, of course, but the timing was appropriate), but they aren't deals that fringe contenders can make because they'd be tantamount to giving up.
Huntington's initial plan was clear: rebuild through the draft and try to strike gold with good-pedigree castoffs to build a team around McCutchen until the farm system was ready. Somewhere in the multiverse, there's an alternate timeline where Lastings Milledge is a 30-homer player and Jose Tabata is a 15-homer guy and Andy LaRoche is a batting champion and Charlie Morton does more than just look like Roy Halladay mechanically and those players with McCutchen and Neil Walker took the Pirates to the 2011 NL Central title and who knows where beyond.
Things didn't work out so well in our reality, though, and now the Pirates are in no-man's land. They have McCutchen and something that vaguely resembles a supporting cast around him right now, but help probably isn't coming until 2013 at the earliest. I hate to be that guy and I very seriously hope I'm wrong, but there's an awfully good chance that Andrew McCutchen is going to be a free agent after the 2015 season. Even on their most accelerated timelines, the first full season that the Pirates will have Jameson Taillon and Gerrit Cole in the rotation is probably 2014. It's not hard to see that that doesn't match up well.
The Pirates' theoretical window doesn't have to close with Andrew McCutchen leaving, of course. The bulk of Huntington's draft acquisitions will probably be arriving around 2014 or 2015 and if they end up with a major excess of pitching, they can swing some trades and be in good shape as guys like Cole and Taillon and Josh Bell (hopefully) hit their primes. That's not even remotely a given, though, because we're talking about two pitchers and a guy that probably went to his senior prom four months ago.
This puts the Pirates in what can be a dangerous position for a small-market club to be in. The club has exactly one blue-chip asset with a known value: McCutchen. They have prospects, but prospects aren't known and they might not mature in value until McCutchen is gone. The situation would be similar to the one that Huntington inherited in 2007, except that they do have prospects in the minors. The problem is that if they trade prospects to bolster this team, they risk not getting there and ending up in the same place they've always been, but if they wait on the prospects they essentially waste McCutchen in the same way that they wasted Kendall and Giles and Bay before him with no guarantee that the minor league system is good enough to make the next wave different.
There's no easy solution, but it seemed to me that the Pirates did a decent job of bridging the gap in 2011. Basically, they put their young, talented players in place, then they tried to fill every gap they could with veterans that would be good enough to give the young, talented guys a chance to make something interesting happen. That's a long shot and it ended up falling apart in 2011 because the young guys didn't come as far as we'd hoped and a few of the veterans weren't good enough, but it's not really impossible. It got the Pirates a memorable 100 games in 2011 without costing them anything in the long run and heck, that sort of plan got the Reds a division title in 2010.
I think it'll be awfully hard to replicate what happened in 2011 without Maholm in the rotation (and, to a lesser extent, without Doumit or Snyder in the lineup), though, for reasons that we've been discussing ad nauseum for a month. It's possible, for sure, because it's a long off-season and the Pirates have money to spend and some minor league assets to trade, but right now I have the creeping feeling that we're headed into another wasted season in 2012 and I was really hoping we'd be beyond that at this point.
As far as "replicating what happened in 2011", I think it's helpful to remember that, despite the Prague Spring of mid-season (and it was truly a joy, no denying that), the Pirates were a 90 loss team last year, and a 90-loss team on merit. When you talk about how narrow the Pirates window is to contend, that is a harsh fact that Pirate fans simply have to live with, or at least will until such a time that MLB realizes that a measure of financial parity seems to work for other professional sports. I remeber Kevin Towers, when he was GM in San Diego, saying (and I'm paraphrasing here) that they went through cycles of rebuilding, then picking one or perhaps two seasons where they felt they would contend as the time to concentrate their resources, and then start the cycle again. This is the Pirates fate as well; they're going to have to point to 2013 and/or 2014, hope for the best, and start the building process again.
The failure to adequately bridge the gap is a larger disaster than you mention, I think. By not attaining value for the trade chits, the Pirates hamstrung their efforts to be competitive. The Pirates have spent a lot of money in the draft. The Pirates have only begun to process those players through the system. Because the system is built on high cost pitchers, the chances of failure are quite high - nothing to date suggests the Pirates know how to develop prospects into productive major league players. And using them as trade chits is as equally fraught with peril - Huntington has not shown himself to be a master trader by any stretch.
As for this - "It got the Pirates a memorable 100 games in 2011 without costing them anything in the long run and heck, that sort of plan got the Reds a division title in 2010."
Aside from salary the Pirates had to spend to make the MLBPA happy, you are correct. However, why were the Pirates so far off as compared the Reds in 2010? That would be an interesting comparison, but the blunt fact is the Reds have done a better job developing prospects into players. When the Pirates shows they can do the same, they may become competitive, but it is no guarantee, especially when the bet is on HS pitching translating into major league pitching.