I've been thinking about doing this for a while now.
I firmly believe that the current Pirates front office has the correct model for long term success at the Major League level. The focus should clearly have been solely on the farm system the first couple of years and then turned into 50/50 minors and majors. The reason for this approach can be seen with the Latos and Gonzalez trades and the Rays model (ie. Matt Moore, Hellickson etc.). If we have the necessary farm pieces we don't have to compete/overpay Free Agents. High caliber free agents that command multiple year contracts can cripple a small market franchise.
With that being said, they have failed to fully maximizing their approach of building from the farm system on up. I know hindsight is 20/20 but I think it is worth noting some of the failures of Huntington and company.
I apologize if I miss any examples. I also want to point out that it seems that around 2010 the Pirates FO recognized some of their mistakes and have adjusted.
In my opinion Huntington and Company have made mistakes in three major areas.
1. Amatuer signing failures - Miguel Sano, Cheslor Cuthbert, Tanner Scheppers, 2010's draft class (specifically HS pitchers)
Imagine a farm system with Cole, Taillon, Bell, Heredia, Marte, Sano, Cuthbert, Allie, Sanchez, Scheppers, Hursh, Emanuel, Kubitza, Weiss, Kime, Grossman, Kingham, etc.
I know that each example of missed signings have their own story and I understand that teams miss out on players all the time but we need to maximize our drafts and missing out on those HS pitchers in 2010 kind of hurts. They need to get better at locking down talent and I feel they have at least honed their skills (Bell, Heredia and Allie). I am also hopeful because it appears that they are doing a better job of recognizing talent at the amateur level.
2. The 2009 draft class - I have no problems with their approach of drafting Tony Sanchez at number 4 and then spreading the wealth to the rest of the class. I have no problems with drafting Dodson, Cain, ZVR etc. What I have a problem with is the selection of Victor Black, Pounders, and Chambers. The first three rounds were protected by the compensation system (I know Black doesn't count because he was compensation from not signing Scheppers), so the Pirates should have drafted higher profile/riskier players. The first few rounds are essential to adding talent to the system and they failed to do so in 2009.
For example, these are players that we drafted and the ones we could have drafted at those positions.
49. Victor Black, 53. Brooks Pounders 84. Evan Chambers,
While this is slightly saddening, I do think the Pirates have adjusted their approach (2010's draft with Taillon, Allie, Rojas and 2011's draft of Cole, Bell, Dickerson). It remains to be seen whether or not they will turn out but this is the appropriate strategy.
3.) Failure to hit on free agents and reclamation projects - Milledge, Clement, Bobby Crosby, Church, Iwamura, Diaz, Overbay etc. This is important because a.) it lost us more games and b.) we couldn't trade them for better prospects. I think that Bedard, Barmes and McGehee represent a better approach to this aspect (this might just be my personal opinion).
I do realize that hindsight is 20/20 and any team could look back on their mistakes. I just feel that Huntington and company could have done a better job early in their tenure. I also feel they have adjusted and are taking the necessary steps to truly "flooding" the system, which in turn will help at the major league level.
Huntington should now go out and sign Jorge Soler and Roy Oswalt.