The Pirates have spent the past decade-and-a-half overpaying for marginal free-agents and signing their underwhelming homegrown talent to huge multi-year deals after they are past their primes.  Then they run out of money because they are a small-market team with a historically unsupportive fanbase and settle for a 70-win season.  Now they are trying a different approach; trading all of the bad contracts from the previous regime and even some players signed to reasonable contracts while those players are at their highest value. A seemingly sound strategy (though try telling frustrated/ignorant Pirates fans that), but only if they are able to get some talent in return.

So how did the Pirates do in their many deals this summer?  With prospects involved, it's always hard to judge right away.  But not impossible.

Alongside the prospects listed in this piece, I have listed their organizational ranking in the 2009 Scout.com Prospects Guide Magazine.  The magazine has the 20 best prospects in each organization ranked.

Pirates trade LHP John Grabow and LHP Tom Gorzelanny to the Cubs for RHP Kevin Hart (9), RHP Jose Ascanio (NR), and 2B Josh Harrison (NR)

The Cubs were desperate for left-handed pitching, as they had been using Sean Marshall virtually every day since moving him into the bullpen (In fact, Lou Piniella found a way to use him three times in a split double-header against the Cardinals).  John Grabow is a great lefty to have out of the pen, and Gorzelanny should only be needed for a few weeks while the rest of the Cubs staff gets healthy.

The Cubs relinquished Kevin Hart, who despite a couple of decent recent starts, has walked nearly as many major league batters as he has fanned and sports a minor league ERA of 4.08.  That ERA has been better the past two years, but then, you kind of hope that 26-year old pitchers post a sub-4.00 ERA in the minors.  The 24-year old Ascanio's numbers are good in both the majors and the minors.  His acquisition is sensible for the Pirates, who just need competent relievers and could care lass as to whether they throw lefty, righty, or head-butt the pitch towards the plate so long as the guy's effective.

Harrison is currently a .319 career hitter in the minors. He can walk, steal bases, and may even develop power.  Considering that Cubs second baseman have gone .227/.281/.327 so far this year, it's hard to figure why they let this guy get away.  Teams tend to overvalue left-handed relievers at the trade deadline, and that seems to have been the case here once again.

Grades: Pirates - A, Cubs - C

Pirates trade Freddy Sanchez to the Giants for RHP Tim Alderson (4)

Alderson is the best prospect the Pirates acquired this year.  This 22nd-overall pick in 2007 had a 20-6 professional record at the time of the deal, and brings a good mix of stuff and command to the table.  All they had to relinquish in order to get him was Sanchez, who refused to sign a contract extension at a hometown discount, then cried when he got traded to a contending team.

It's hard to say whether the Giants were dazzled most by Freddy's resume of being a three-time All-Star, his empty batting average, his bad contract, or the fact that he is on the wrong side of 30.  He does provide solid defense, a bat that is unlikely to downgrade an underwhelming lineup, and good doubles potential in a park that facilitates two-baggers, but when he reaches his 600th plate appearance this year, his $8 million option for 2010 vests.  At least the Giants might not miss Alderson much, with Madison Bumgarner preparing to overshadow Tim Lincecum in what is becoming a stacked rotation.

Grades: Pirates - A, Giants - C

Pirates trade Ian Snell and Jack Wilson to the Seattle Mariners for Jeff Clement, Ronny Cedeno, RHP Nathan Adcock (17), RHP Aaron Pribanic (NR), and RHP Brett Lorin (NR).

Wilson, like Sanchez, refused Neal Huntington's request to take a hometown discount to stay in Pittsburgh.  Monetarily, Wilson made the right move, as the Mariners pretty much need to pick up Jack Rabbit's $8.4 M option for 2010 and hope he hits like he did in 2004 or 2007 in order to justify this deal, seeing as how the Mariners are out of the race this year and even more so after dealing away Jarrod Washburn.  More likely, they will pay $8.4 M for a good-field, no-hit shortstop.  An upgrade over Yuniesky Betancourt to be sure, but a total ripoff as well.

They do get Ian Snell in the deal, whom I had fallen in love with before he had even reached the majors.  He's been difficult to love over the past year-and-a-half, however, and even though I still think he has potential (as evidenced by his recent Triple-A stint that gave Snell his highest trade value since he signed his contract extension), at the end of the day he is a 27-year old pitcher who wasn't good enough to pitch for the Pirates and makes $4.25 M next year.

Adcock is 11-25 in his minor league career.  Pribanic's K/BB ratio is less than 2:1.  Ronny Cedeno is Ronny Cedeno.  The only real losses for the Mariners here are Lorin, who has fanned more than a batter per inning in his career, and Clement, who was never going to get a legitimate shot at winning a major league job in Seattle for whatever reason.  The question becomes, why the heck isn't Clement the everyday first baseman in Pittsburgh right now?  For a third overall draft pick not to be getting a fair shake at a big league job after nearly three full successful Triple-A seasons is simply unheard of.

Grades: Pirates - B, Mariners - C

Pirates trade Adam LaRoche to the Red Sox for SS Argenis Diaz (13) and RHP Hunter Strickland (NR)

Okay, now we are getting into some older trades that we can begin to evaluate with some hindsight as well as projection.  LaRoche was nothing special for the Red Sox, though they were inexplicably able to parlay him into the underrated/underpaid Casey Kotchman weeks later.  I bet if the Pirates knew that they could get Kotchman for LaRoche straight up, they'd have thrown in Snell for free as a goodwill gesture.

As it is, they settled for two forgettable prospects.  Diaz is supposedly a great defender, but there is no reason to believe that he will ever hit well enough to start at the major league level.  Every minor league system has a handful of Argenis Diazes.  Strickland has done well as a good-control/no-stuff pitcher at the low-A levels.  Those kinds of pitchers tend to get exposed long before they reach the majors.  Still, getting Boston to shoulder all of LaRoche's remaining $3 million was a feat in itself, even if the returns were minimal at best.

Grades: Pirates - C, Red Sox - B

Pirates trade Nyjer Morgan and Sean Burnett to the Nationals for Lastings Milledge and Joel Hanrahan

This is the only recent Pirates trade that wasn't unbalanced in terms of established major leaguers being dealt for prospects.  All four players dealt here are essentially fringe major leaguers, with the difference being that the two players the Pirates received actually have some upside.  Now granted, Morgan has been unbelievably excellent for Washington, batting .387 with 14 stolen bases in 28 games.  But the man is 29-years old and speed is his best weapon.  He is a player who might help in the short-term, but not someone who is likely to have a lengthy major league career.  So why the last-place Nats would trade for him and a southpaw that is neither a power pitcher nor a control pitcher is quite baffling.

Believe it or not, Lastings Milledge is still just 24-years old, and he's already shown flashes of star ability in the majors. He's also shown flashes of being a real jerk, but you know what?  I bet if Barry Bonds had stayed in Pittsburgh, the fans there would have overlooked all of his personal shortcomings and cheered him like no one since Roberto Clemente.  I'm not a big Hanrahan fan, as he is nearly 28 and still has not learned how to throw strikes, but he does throw heat and still has a slim chance of becoming a plus-reliever.

Grades: Pirates - A, Nats - C

Pirates trade Eric Hinske to the Yankees for RHP Casey Erickson and OF/C Eric Fryer

Hinske has been fabulous for the Yankees, smacking five home runs in his first 21 at-bats with the club.  To be fair, no GM - not even Brian Sabean - would have thought that Hinske would have had this kind of an impact for a team.  So we can't fault the Pirates for not getting equal value in the trade to what Hinske has suddenly become.

Fryer played a lot of outfield this year only because the Yankees are loaded with catching prospects.  His future is as a catcher, though it's hard to project him as a starter in the big leagues.  Erickson has put up stellar minor league numbers, but generally as a guy too old for his level.  He is already 3-1 with a 0.87 ERA for the Pirates, but that's in Single-A.  The guy turns 24 this month... isn't it time to see what he can do at higher levels?

Grades: Pirates - C, Yankees - A

Pirates trade Nate McLouth to the Braves for Charlie Morton, OF Gorkys Hernandez (7), and LHP Jeff Locke (10)

I wrote about this one before, claiming that while trading the overrated McLouth at peak value was a great idea, that they had perhaps forgotten to get that peak value in return.  Since that time, Charlie Morton has been  one of their best starters, but Gorkys Hernandez and Jeff Locke have both been terrible in the minors.  On the other hand, McLouth has been just decent as a leadoff man for the Braves.  The Pirates will soon have an outfield that features some combination of Andrew McCutcheon, Jose Tabata, Garrett Jones, Lastings Miledge, Steve Pearce, and Delwyn Young.  The three prospects they got in return for McLouth aren't going to need to set any records for this to be a decent trade, because by 2011, the Pirates will have three or more outfielders outperforming McLouth at a much more affordable price.

Grades: Pirates - B, Braves - B

The Pirates have stockpiled enough young talent to allow for many of their prospects to go bust and still field a competent team.  They will need to add some veteran help over the next two seasons to supplement this core, but Neal Huntington has freed up enough salary to make doing so fairly easy.  Do not despair, Pirates fans.  The end of your losing ways is nearly at an end.  When the team does start winning, please go watch them at beautiful PNC Park.