Of the 25 Pittsburgh Pirates who took the field on Opening Day 2008, 7 remain with the organization today. General manager Neal Huntington has turned over his depth chart methodically and added a number of talented prospects to his farm system. Doing so was not easy. Huntington sent away All-Stars in Jason Bay, Nate McLouth, Freddy Sanchez and Jack Wilson in the past year, undoubtedly frustrating the average fan in the process.

Considering a streak of 16 consecutive losing seasons is likely to be extended once again come October, no one would blame yinzers for questioning the team’s intentions. Five-year rebuilding plans have come and gone with no results. The current roster features 1 player over the age of 30 — utility infielder Ramon Vazquez — and millions of dollars have been slashed from the payroll.

Huntington’s late July fire sale included deals for Sanchez, Wilson, Ian Snell, John Grabow, Tom Gorzelanny and Adam LaRoche. Sean Burnett, traded with popular outfielder Nyjer Morgan to the Washington Nationals in June, recently called the Pirates the laughingstock of the league. And maybe there was truth in Burnett’s outburst — despite being considered winners at the trade deadline by national baseball writers, the team had turned into a punchline. Huntington listened to offers on everyone and anything, including the kitchen sink, in the nearly unprecedented sell off.

But what choice did he have?

The GM entered an impossible situation when he inherited Dave Littlefield‘s job. The major league roster was weak and aging, but the minors were undeveloped, too. Huntington did what was necessary: He kept what little talent could be controlled long-term and dealt remaining assets at as high a price as the market would bear. For the first time in years, the franchise would develop from within. Littlefield’s goal of reaching a single .500 season would no longer be considered acceptable. The cycle of overpaying role players and ignoring premium talent pools would end.

Huntington deserves the benefit of the doubt, and as soon as this winter he could prove his plan has the team headed in the right direction. After shedding veterans past their primes, targeting players with over-slot bonus demands in the draft and entering the Latin American free agent market aggressively, Huntington can take one more action to assure me that he’s the man who will turn the organization around.

Sign Andrew McCutchen to a long-term deal.

Fans lacking savvy would be quick to point out that Huntington extended McLouth, Sanchez and Snell, only to trade them away. There’s a difference between buying out arbitration years and cheaply controlling a premium player through three seasons of free agency, though. That’s exactly what the Tampa Bay Rays were able to do with Evan Longoria in April of 2008, just days into the franchise third baseman’s career in the show. There was no doubt that Longoria would emerge as a star, and so the team offered the 22-year-old a guaranteed $17.5 million. The Rays bought out his arbitration seasons and acquired club options for three free agency years.

Longoria could have hit the open market before 2014, and if history is any indicator, the Yankees or Red Sox or Mets or Cubs would have signed him then to a huge, multi-year contract. Instead, should Longoria progress as expected, the Rays can choose to control him from 2014-2016 for a combined $28 million. According to FanGraphs’ value statistics, Longoria was worth $24.1 million in 2008 alone.

It’s now that Huntington needs to sign a player of McCutchen’s star power; he can’t afford to wait until his center fielder can see free agency coming. Give McCutchen a life-changing amount — which $18-20 million certainly is — and ensure that he’ll be a key contributor to sustained winning in Pittsburgh through his physical peak. By all accounts McCutchen is a hard-working, explosive, two-way standout. His debut has quieted even the harshest critics. Prove to him, to his peers and to the Steel City that the Pirates are serious about winning and keeping the best players in Pittsburgh. Piecing together a top farm system is meaningless if All-Stars can’t be retained when they’re needed most.

The sudden and unexpected trade of All-Star outfielder Nate McLouth on June 3 was viewed by many as a microcosm of the past decade and a half of losing.  The Atlanta Braves acquired McLouth in exchange for starting pitchers Charlie Morton and Jeff Locke and outfielder Gorkys Hernandez.  While many experts feel the Pirates will come out ahead long-term — What a haul for an overrated “Gold Glover,” tweeted Keith Law — fans believe the team has given up on its present, and rightfully so.  Same old Pirates.

But there is reason for hope at PNC Park.  Since taking over for Dave Littlefield in September of 2007, general manager Neal Huntington has reshaped the organization.  In his first full season at the helm, Huntington spent a record amount on his June amateur draft class.  He traded two of the club’s prolific veterans, Xavier Nady and Damaso Marte, to the New York Yankees for pitchers Daniel McCutchen, Ross Ohlendorf and Jeff Karstens and outfielder Jose Tabata. Then they traded a third veteran, Jason Bay, to the Boston Red Sox as part of a league-shaking three-way deadline deal.

There is reason to believe that the McLouth deal might work out for the best.

When he traded Nady and Marte to the Yankees, Huntington was smeared on message boards, blogs and talk radio.  Nady was in the midst of a career year, hitting .330/.383/.535 as part of baseball’s most productive outfield, and Marte was a shutdown setup man in the bullpen.  Tabata’s star had fallen since being ranked as the game’s 27th best prospect by Baseball America in 2007, and the pitchers seemed to be castoffs from a team rich in bonus babies with golden arms.

Nearly a year later public perception has turned.  “The move was hailed as a steal for a Yankees club desperately trying to reach the postseason, [but] subsequent events have muddied the waters,” writes Moshe Mandel of The Yankee Universe.  Nady hit just .268/.320/.474 down the stretch and Marte’s ERA ballooned to 5.40 as New York missed the playoffs in 2008, and neither player is contributing much in 2009.

Meanwhile, Ohlendorf has emerged as the Pirates’ No. 3 starter, posting five wins and a 4.45 ERA through 10 starts.  Tabata and McCutchen were ranked as the third and ninth best prospects in the system by Baseball America entering 2009 and appear destined for big-league futures.

The Bay trade was even less popular.  Arguably the team’s most impressive player, Bay was given away for nothing:  The Pirates received outfielder Brandon Moss and reliever Craig Hansen from the Red Sox, and third baseman Andy LaRoche and starting pitcher Bryan Morris from the Los Angeles Dodgers, who had been shipped enigmatic superstar Manny Ramirez from Boston.

Moss and Hansen were viewed as role players on a contending team and nothing more (and perhaps that’s all they are).  Morris’ stuff graded out well, but he had trouble staying healthy; Pirate fans know all about stud pitchers succumbing to Dr. Andrews’ scalpel.  And another LaRoche?  They knew all about those underachievers, too.

The situation got worse in August and September as the power-hitting Moss struck out at an alarming rate.  LaRoche stumbled out of the gate and hit .152/.227/.232 over the remainder of the season, all the while making error after error at third base.  What had Huntington done?

In his first full season with the Pirates at age 25, Bay hit .314/.377/.660 through 50 games.  Eventually, he’d win the National League Rookie of the Year award, and in later seasons would be named to All-Star teams and receive MVP votes.

And in his first full season with the Pirates at age 25, LaRoche hit .297/.366/.424 through 50 games.  His defense seems to be improving at a premium position.  He is a team leader in on-base percentage, and his strong pedigree is showing.  Pirate fans have little reason to doubt him as a cornerstone for the next winning club in Pittsburgh, even if his power is slow to come.

Just as Rome wasn’t built in a day, the destruction left behind by Littlefield won’t be cleaned up in a season or two.  The Bay trade will be judged by the seasons of control exchanged; one and a half of the Canadian left fielder for 20 of the prospects.  The McLouth trade will yield 18 seasons of Morton, Locke and Hernandez.

As the 2009 campaign progressed, Huntington realized that his team’s odds of making the playoffs were slim (Baseball Prospectus figured them at less than 10 percent).  As always, he is building for next year, and for the year after that.  Once again as the trade deadline approaches, he will seek to move veteran contracts in favor of minor leaguers with upside.  Adam LaRoche, John Grabow, Jack Wilson and Freddy Sanchez could all be gone by August 1.  To paraphrase Billy Beane, if you’re not going to win 90 games and reach the postseason, you might as well only win 70.

Combined with aggressive movement in international free agency — the Pirates have been linked to top Dominican prospect Miguel Angel Sano — and keen navigation of the Rule 4 draft, Huntington’s trades should lead to a top-ranked minor-league system and a sustainable winning culture in Pittsburgh.