The Pittsburgh Pirates haven't had a winning season since 1992. I was born in 1991.
It doesn't take a math major to discover the Pirates have been losing for, essentially, my entire life.
Despite the ridicule, consternation, and frustration Pirates fans are constantly subjected to I remain a loyal, hopeful fan. I'll go as far to admit I thought this would be the year they would finally run their record above .500.
Not so much.
Mired in an atypical pathetic season, the Pirates (45-90) aren't much to talk about in strictly baseball terms. That's partly the reason the recent divulgence of financial figures showing the Pirates have turned profits in the tens of millions over the last three seasons has drawn the ire of fans and analysts alike.
The "Why-aren't-they-spending-this-money-on-players?" argument ignores the larger issue at hand: Even if they spent they money, they wouldn't know what to do with it.
Coupled with the organization's notorious stinginess is a severe inability to evaluate talent. Take, for example, some of the team's first round picks over the last decade: SeanBurnett (19th overall 2000), John VanBenschoten (8th overall 2001), Bryan Bullington (1st overall in 2002), and Daniel Moskos (4th overall in 2007).
All were viewed as upper-eschalon pitching prospects. None even approached the billing and only Moskos, who pitched to a 10.38 ERA in his stint with Triple-A Indianapolis this season, remains with the organization.
It's not fair to include any players acquired or dealt in the numerous, shrewd, salary-dumping trades the Pirates have made over the years, but who they could have afforded to keep and did not is still disheartening.
Pitcher Bronson Arroyo was placed on waivers by the Pirates in 2003 and was claimed by the Red Sox, who paid no compensation to get him. Arroyo has since compiled 91 wins including a 14-9 mark this year, a World Series title, and an All-Star appearance, while the Pirates struggle to find a single reliable starter.
Infielder Jeff Keppinger was traded, along with Kris Benson, to the New York Mets for Jose Bautista (remember that name) and Ty Wigginton. Neither of the players acquired are still with the Pirates, but Keppinger is hitting .284 with 28 doubles and five home runs for the Houston Astros. His hitting ability would be a welcome complement to a team that ranks 29th out of 30 teams in MLB in most significant batting categories.
The aforementioned Bautista, a 2010 All-Star, was serviceable but not spectacular with the Pirates. He was always viewed as a potential power hitter by Bucco brass, but topped out at a season high of 16 home runs, consistently posting low batting averages and walk totals. When he was traded for a player to be named later (what an afterthought that guy must feel like) who turned out to be third-string catcher Robinzon Diaz, little fanfare was made.
This season, Bautista has exploded for the Toronto Blue Jays leading the major leagues in home runs (43) and extra base hits (76) while also posting top ten totals in runs (91), RBIs (103), total bases (291), walks (87), slugging percentage (.618), and outfield assists (11).
In 2010, the organization has poured their resources into acquiring young talent through draft and have paid above slot value for highly regarded prospects like JamesonTaillon, Stetson Allie, and Mel Rojas Jr. I find myself encouraged by the signings, but tempered by past disappointments.
The inability to evaluate talent has transcended regimes, decades, scouts, and general managers.

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