Found December 30, 2009 on Pirates Prospects: Yardbarker Blogger Network
Today we continue the "Decade" series with the worst trades of the decade.  First, a review of what I've covered so far:

Top 10 Draft Picks of the Decade
Worst 10 Draft Picks of the Decade
Top 10 Free Agent Moves of the Decade
Worst 10 Free Agent Moves of the Decade
Best Trades of the Decade

Before I begin on the worst trades of the decade, I wanted to address a few things about the evaluation of trades.  I touched on this yesterday, but in the end, I think the Xavier Nady trade will come out as the best deal of the decade.  However, all ratings are based on right now.  Potential does play in to my ratings, but I do factor in the chance that some things just won't work out as we hope.

For example, if Jose Tabata flops, Ross Ohlendorf regresses, and Daniel McCutchen doesn't work out in the rotation, it would be hard to call the Nady trade number one.  I don't think that chain of events will happen, but that's not a guarantee.  I also can't rate a trade like that over deals that brought the Pirates years of production from Jason Bay, Freddy Sanchez, and Jack Wilson, at least not at the moment.

It's for this same reason that you won't see the Jason Bay trade on this "worst" list.  Well, the ultimate reason is that, despite the trade getting horrible reviews, Andy LaRoche was a 2.5 WAR player in 2009, compared to Jason Bay being a 3.5 WAR player.  When you trade one year of a 3.5 WAR player for six years of a 2.5 WAR player, you don't lose the deal.  That's just my opinion.  Also, LaRoche's value is heavily based on his defense, while Bay takes a huge hit on defense.  There's still a chance that LaRoche increases his offensive production.  Bay isn't going to be increasing his defensive production.

I also refrained from including trades that we don't know much about.  For example, in the comments yesterday, the Gorzelanny/Grabow trade was predicted to be one of my worst deals.  I don't have it on the list because there hasn't been enough time to evaluate the deal.  Same with the McLouth trade, which I didn't include in my "best" list, even though I think could emerge as one of the best trades, right behind the Nady deal.  I didn't include it because it is mostly based on potential right now.

That said, let's get on with the trades...


5. Jason Schmidt/John Vander Wal for Ryan Vogelsong/Armando Rios, July 2001

Schmidt had a lot of potential, but never lived up to it in Pittsburgh, with a 4.39 ERA and a 1.44 WHIP in 799.2 innings with the Pirates.  He immediately had success in San Francisco, including being a Cy Young candidate in 2003 and 2004.  Vander Wal had some success in his brief stay with the Pirates, hitting for a .290/.389/.522 line with 35 homers in 697 at-bats.

Vogelsong was the number five prospect with the Giants heading in to the 2001 season, projected as a number three starter.  It's hard to say how much his injury factored in to his failure in the majors, but the bottom line is that the Pirates traded a talented, yet struggling, pitcher, and a productive player in Vander Wal, and in return received nothing in the long run.



4. Rajai Davis for Matt Morris, July 2007

The Giants were trying to get rid of Matt Morris and his salary, and were having a hard time doing so.  Morris was in the decline of his career, with a 4.98 ERA in 2006, and a 4.35 ERA in 2007 before the trade.  He was also guaranteed over $11 M after the 2008 season, plus the remainder of his $10 M 2007 contract.  He's not exactly the type of guy you want to dedicate 20-25 percent of your payroll towards in the first place, but I find it hard to believe that he would have cost this much.

Usually in deals like this the trading team either takes organizational depth in exchange for the acquiring team taking on the full salary, or the acquiring team gives a decent player in exchange for salary relief.  The Pirates not only took on the whole salary, but gave up Rajai Davis, who is a decent bench player at worst, and could be Nyjer Morgan at best.  Morris ended up bombing in 2008, and finally left the books after the 2009 season.  For all the complaints about the Pirates failing to add to the 2008 offense, imagine what they could have done with an extra $11 M to spend if Morris wasn't around.


3. Kris Benson/Jeff Keppinger for Ty Wigginton/Jose Bautista/Matt Peterson, July 2004

I don't grade trades based on speculation and rumors.  I also don't grade them based on theories of alternative returns in the deal.  However, that's hard to do in this situation.  First, there are the rumors, some confirmed, that the Phillies offered Ryan Howard for Kris Benson, and Dave Littlefield turned down the deal because he felt they had Ryan Howard in Brad Eldred.  Second, there's the other trade the Mets made, sending Scott Kazmir to the Tampa Bay Rays for Victor Zambrano, who was in no way considered better than Benson at the time.

Now I'm not sure if Kazmir was offered for Benson, but I do know that Benson was the better pitcher the Mets received, and I can't imagine that the Pirates couldn't have received Kazmir for Benson.

This trade perfectly sums up everything that was wrong with Dave Littlefield.  First, you've got trading for Ty Wigginton.  Littlefield went for need over talent, going for their need at third base, rather than a better talent in Howard or Kazmir, assuming Kazmir was available.  Littlefield also didn't stress a need for quantity with prospects.  As we know, prospects aren't a guarantee, which means it's foolish to count on one prospect like Eldred to pan out, and pass on an equally talented prospect in Howard.  This also shows the mis-management Littlefield had with prospects, giving Jeff Keppinger away in the deal, in order to recover Jose Bautista.  Finally, it seems that a lot of moves Littlefield made were made to appease the fans, rather than sound baseball decisions.  The decision to bring Bautista back is a prime example.  Littlefield didn't care for Bautista enough to protect him from the Rule 5 draft, so why did he care enough to trade for him half a year later?  Perhaps because he was widely panned for the decision to leave Bautista unprotected in the Rule 5 draft?



2. Chris Young/Jon Searles for Matt Herges, December 2002

Young was coming off a great season in which he posted a 3.11 ERA in 26 starts in low-A ball, with an 8.5 K/9, a 2.1 BB/9, and a 0.7 HR/9.  Herges had a 4.04 ERA in 64.2 innings of relief in the majors with Montreal in 2002, but had a 1.64 WHIP and a 1.4 HR/9.  The decision to trade for Herges wasn't horrible by itself.  In hindsight the deal was poor because of what Chris Young became, although Young was traded twice before becoming the pitcher he now is.

The problem was that the Pirates traded Young for Herges, then cut Herges before the season began.  Herges went on to put up a 2.62 ERA in 79 innings of relief, with a 1.23 WHIP in 2003.  So the Pirates essentially gave Chris Young away for nothing.


1. Aramis Ramirez/Kenny Lofton/Cash for Bobby Hill/Jose Hernandez/Matt Bruback, July 2003

This may go down as one of the worst trades in baseball history.  To recap the events, the Pirates were forced to get rid of salary to comply with MLB's debt ratio.  Kris Benson went down with an injury, leaving Ramirez as the only trade option.  The Pirates traded him to the Cubs on July 23rd for Jose Hernandez, Matt Bruback, and a player to be named later.

As if that wasn't bad enough, the Pirates also threw in Kenny Lofton, who was having a decent year batting leadoff and playing center field for the Pirates.  To top it all off, the Pirates included cash in the deal, as if the Cubs needed that incentive to make this deal.

Jose Hernandez was a 33 year old infielder who was a utility player at best.  Prior to the 2003 season he had a career .255/.314/.429 line in 3502 at-bats, with 1053 strikeouts.  Hernandez was let go after the season.  Matt Bruback was a 24 year old starting pitching prospect in AAA.  He never reached the majors, but that doesn't excuse the foolish decision that was made with him.  When the Pirates added the player to be named later, Bobby Hill, they designated Bruback for assignment.  Bruback was claimed by the San Diego Padres, thus limiting the return to Hernandez and Hill.

Hill was a valued prospect, but as was often the case with Littlefield, he put all of the prospect eggs in one basket, which isn't the best strategy to take.  Hill hit for a .267/.352/.337 line in 329 at-bats during his time with the Pirates.  Overall, that's what the Pirates received for two and a half years of Ramirez, half a year of Kenny Lofton, and cash to cover their salaries.  Half a season from Jose Hernandez, a few AAA starts from Matt Bruback, and 329 major league at-bats from Bobby Hill.


Honorable Mentions

Leo Nunez for Benito Santiago and cash, December 2004

Damaso Marte/Edwin Yan for Matt Guerrier, March 2002 (The Pirates traded for/received Marte in four different deals this decade.  In this one they let Guerrier walk a year later.)

Gary Matthews Jr for cash, December 2001 (Matthews was purchased by the Mets)


Check back tomorrow for the worst moves of the decade...


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