From a tangible angle, Sunday was a good day for Dave Littlefield. The ever-rebuilding Pittsburgh Pirates swapped a 34 year old free agent to-be for a player that finished a not-so-distant third in the 2003 Rookie of the Year voting. Unfortunately for Littlefield, currently in his fifth season running the Bucs, general managers are not always evaluated from a black-and-white approach. It's the speculation that could very well lead to Littlefield's firing.

There is no doubt many Pittsburgh fans will call for the axe of their GM, who arguably entered Deadline Week with as many bargaining chip pieces as any other seller. An organization that has gone 292-373 under his tenure was in desperate need of the yield that veterans like Jose Mesa, Mark Redman, Rick White, Kip Wells, Daryle Ward and Matt Lawton could have provided. Instead, Littlefield got just one of the six, much like the Bucs on their current road trip.

We have no way of knowing what transpired on Littlefield's cell phone in the past week, besides knowing it wasn't enough to convince him to pull the trigger. But it's hard to believe a market that paid two prospects for the likes of Ron Villone would not take a closer like Mesa. Or if Shawn Chacon of all people can net two players, there isn't anything that Redman or Wells would bring? Our educated guesses that contradict the front office may just be enough to bring an end to a legacy that has been spotty at best.

On the trade market, Littlefield has been very up and down since taking hold of the Pirates a few weeks before the 2001 deadline. Six times has he dealt players perceived as being very good on the market, twice of which ended fantastically. First was Todd Ritchie, in the 2001-2002 offseason, when Kenny Williams tried to solve the White Sox pitching problems by trading Kip Wells and Josh Fogg. Ritchie was nowhere near as valuable for the White Sox in 2002 than either Wells or Fogg was for Pittsburgh.

The Ritchie trade was the second of its kind, and followed Littlefield's first real disaster. Just seventeen days after Kevin McClatchy named him the general manager, Littlefield dealt the enigmatic Jason Schmidt to San Francisco. His return? None other than the still-horrible-after-steroids Armando Rios and arm problem riddled Ryan Vogelsong. Schmidt went on to put things together in San Francisco (with Barry Bonds), and led the Giants to a World Series, while the Pirates have received little-to-negative value for the package.

If we can say those two nullified each other, Littlefield can hope for the same of his midseason 2003 trades. Again, the first of the two was bad, when the Pirates packaged both franchise player Aramis Ramirez and Kenny Lofton together for the in-division Cubs. In return, Jim Hendry sent veteran and free-agent-to-be Jose Hernandez as well as minor leaguers Bobby Hill and Matt Bruback. Hill was a well thought of second base prospect that couldn't break Don Baylor's lineup, and Bruback a mid-grade pitching prospect. Since, Hernandez moved on quickly, Bruback didn't materialize, and Hill is only beginning to pay any sort of a dividend.

After that, July 31 came and passed in 2003 without Littlefield letting go of Brian Giles. The star outfielder had been rumored in trades for seasons, but the peak came that July. Towards the end of that August, a team finally met Littlefield's high demands, when the Padres claimed Giles in minors. Their payment for the saber-friendly outfielder was pitching prospect Oliver Perez, recently-acquired Jason Bay and Cory Stewart. Perez had been called by Barry Bonds as one of the game's best young lefties, and Bay was in the middle of a huge season at AAA. The two quickly became integral pieces for the Pirates in 2004, and figure to do the same well into the current rebuilding plan.

Since 2004, there have been two more trades, both with players that had been long-rumored like Giles. Kris Benson had a golden arm on Team USA as an amateur, but arm problems led to consistent underperforming. He finally was traded last July to the Mets, in an odd three-way, in which the Mets dealt Justin Huber to the Royals for Jose Bautista, so they could team him with Ty Wigginton and Matt Peterson in a trade for Benson. Wigginton quickly went on Lloyd McClendon's bad side after a horrendous start with the Pirates, playing himself out of long-term plans. Peterson looks to be a player in the same mold as Bruback and Stewart, which is hardly a compliment. The prize of the deal should be Jose Bautista, maybe the third baseman of the future, but still hardly as valuable as Huber. While this doesn't look like a great deal, the jury is still out here.

Finally, after these five, Littlefield felt it was time to step in the ring with the trade master: Billy Beane. Needing a high-OBP catcher for his rebuild, Beane quickly turned to Jason Kendall, who signed a too-costly extension with the Pirates that ownership did not like. So, Kendall was traded just for two veterans, Mark Redman and Arthur Rhodes. The latter was then quickly shipped off for Matt Lawton, who of course, brings us back to where we started. The Kendall deal wasn't awful either, but the inability to land one player under thirty was disappointing.

While those are the big deals of Littlefield's tenure, they are surely not his worst. Those instances tend to always happen in the same scenario: when Littlefield tries to acquire veterans to fill Major League holes with his farm system. While it has paid off once (Randall Simon), the methodology has also backfired in very unnecessary ways. After heisting the White Sox of two good starters, Littlefield allowed Kenny Williams to salvage the offseason when he gave him Damaso Marte for Matt Guierrier.

The next offseason, a reliever was needed, so the Pirates turned to the Expos' Matt Herges. The price? Chris Young, all 6-10 of him, who is now thriving in Texas. Finally, while it doesn't look so bad, I get the feeling in a few years we will look back negatively on Littlefield's acquisition of Benito Santiago for Leo Nunez. The Pirates pitching staff would sure look better with Marte, Young and Nunez than it does now, and would have more than allowed for some of the veterans to go.

In both Marte and Young, Littlefield and staff drastically underestimated the talents they had. This is a problem that has happened time and again for the current player development staff. This is a staff that waived Bronson Arroyo in need of a 40-man spot, and watched him go on to pitch in the World Series for the Boston Red Sox. Or how about Duaner Sanchez, another waiver wire claimee, this time by the Dodgers, who have since inserted Sanchez into some high-leverage situations.

They also have been pickpocketed a few times by the Rule 5 draft, when players were inexplicably left off the 40-man roster. The best example is Chris Shelton, the first player drafted by the Pirates in December of 2003. Shelton is now a middle-of-the-order hitter for the Tigers, while the Pirates found him to be about equal to the likes of J.R. House. Other players that stuck in opposing organizations after being drafted include D.J. Carrasco -- who put up one solid season in K.C. -- and Chris Spurling.

Still, it would not be fair to evaluate Littlefield without giving him credit for where the Pirates are headed. First of all, you like to see any organization have a plan for future success. And I'm told by a Pirates source that the club has certain preferences for players, tailor-made for PNC Park. They are:

1. Left-handed power hitters: Short porch in right field.

2. Left-handed college pitchers: Heady pitchers that nullify opposing LH hitters.

3. Left fielders with range: One of two stadiums in the Majors in which LF must cover more ground than CF.

It also appears that the Pirates are sticking to this plan. In each of his last three drafts, Littlefield has spent a first round pick on a player that fits this criteria: Paul Maholm (LHP), Neil Walker (LH power), and Andrew McCutchen (speedy OF). We have also seen these preferences through other outlets, like Zach Duke and Mark Redman or Daryle Ward and Matt Lawton, and finally Jason Bay and Jody Gerut. The combination of an intelligent plan and dilligency to stick to it bode well for future success.

As does a very good young core, which is centered around Bay and Perez. Joining Oliver in the rotation will surely be Duke, who has been fantastic so far this season. Duke has been compared to Tom Glavine on numerous occasions now, and he has shown the ability to pitch without his best stuff. Ian Snell should also be there, after impressing the organization a great deal the last two seasons. The club also hopes Duke-like southpaw Sean Burnett bounces back from surgery successfully next season. Finally, the organization also has high hopes for former high picks Maholm and Gorzelanny, both pitching well at high levels.

On the offensive side, things look far less impressive. The middle of the infield should be Bobby Hill and Javier Guzman, both players that should boast modest OBPs in the future. The corners are looking like Brad Eldred and Jose Bautista, with the former joining Bay in the middle of the order. The club is definitely hoping Jody Gerut reverts to his old form in the outfield, where he should be with Bay and Craig Wilson. That is, if Wilson can ever stay healthy for 10 games. He will also be the first to be replaced should McCutchen rise through the system quickly.

Still, don't expect the base to be enough for Littlefield to salvage his job much longer. Ownership has put up with a lot in the past regarding the front office, and is still waiting for its first good post-Bonds team. After Sunday, they would be foolish to think that will happen soon with the same arrangement. While we'll never the details of Littlefield's last week, enough people will be guessing the same thing, and that should lead to a forthcoming replacement.