When looking through some drafts from early in the 2000s- most notably 2002- I noticed the Pirates incompetence in the draft, and figured it'd be fun to make a hypothetical team for the Pirates assuming a few things- they drafted the best player that went after their slot at the position they drafted for, and that cost wasn't an issue, so they still own all of these players. The second issue is better explained by Longoria-like extensions signed earlier on. Using this model, I'm going to estimate their optimal 2011 team and their optimal farm system going forward.
So, without further ado:
2002: The Bucs drafted Bryan Bullington with the first overall selection in the 2002 draft- he of -0.4 career WAR. In the first round of that draft, Zack Greinke, Jeff Francis, Joe Saunders, Scott Kazmir, Cole Hamels, Jeremy Guthrie, Joe Blanton, and Matt Cain were all also selected. The worst of those, as ranked by career WAR, is Francis at 7.9. The rest all have over 10 WAR, with Greinke, Cain, and Hamels all over 20 and still young and under team control so we can assume had Pittsburgh chosen one of them they'd still have them- the teams that signed them still have them with the exception of Kansas City who traded Greinke with multiple cost-controlled seasons still on his deal last offseason. I'm going to say they draft Greinke, because he went towards the top of the draft so there's a good chance he was one of their top options after Bullington.
2003: The Bucs drafted Paul Maholm one slot ahead of still-team-controlled John Danks, and way ahead of Chad Billingsley. Since they were a slot apart I'll give them Danks. So now they have a staff of Danks and Greinke.
2004: They chose Neil Walker with their first selection, which is turning out to be a fine selection.
2005: They chose Andrew McCutchen here. Another great decision.
2006: They picked Brad Lincoln, one spot in front of Brandon Morrow and three in front of Clayton Kershaw. Also picked in said first round were: Tim Lincecum, Max Scherzer, Kyle Drabek, Ian Kennedy, Daniel Bard, Joba Chamberlain, and Chris Perez. Ian Kennedy looks like a solid median selection here, but they had an early pick so let's say they choose Kershaw- this is hypothetical, after all. So now its Walker/Kershaw/AMC/Greinke/Danks- an unbelievable under-team-control core heading into 2012.
2007: My goodness, what a disastrous pick. They chose Daniel Moskos, another pitcher. One spot in front of 2012 break-out candidate catcher Matt Wieters, and a few spots in front of insanely talented and hyped hurlers Jarrod Parker and Madison Bumgarner. Jason Heyward also went later in that same draft. Lets say they choose Parker because I've been too generous with optimal situations and Bumgarner has been awesome. Oh boy.
2008: They drafted Pedro Alvarez who seems to have talent, so solid pick.
2009: They took catcher Tony Sanchez. Lets do a switcharoo because I like Jacob Turner more than Jarrod Parker and I'm running this hypothetical Pirates team. I'm going to say we draft Matt Wieters in 2007 and Jacob Turner in 2009. Both end results are a catcher and a starting pitcher- just, the better catcher and better starting pitcher in each result.
2010: Jameson Taillon! I like this kid's potential.
2011: Gerrit Cole! Another pitcher whose potential I love.
In my hypothetical world, this Pirates team enters 2012 with Matt Wieters at catcher, Pedro Alvarez at third base, a rotation with Jacob Turner, Zack Greinke, John Danks, and Clayton Kershaw, and one of James McDonald/Jeff Karstens/Charlie Morton, a closer in 30-year old Joel Hanrahan, Clint Barmes at shortstop, Neil Walker at second base, somebody at first base, and an outfield of Andrew McCutchen, Garret Jones, and Jose Tabata, with Gerrit Cole and Jameson Taillon waiting in the wings for the future when one or more of those pitchers leave.