Five Previous Deadline Deals that Define the 2009 Pittsburgh Pirates

As a small market team, the Pirates are constantly wheeling and dealing—usually selling higher-priced players for prospects—and these trades constantly reshape the franchise.

Over the past 17 years, not much has gone right in Pittsburgh, including on the trade front. But there have been a couple bright spots, and they have resulted in the Bucs' few post-Barry Bonds stars.

This slideshow highlights the five biggest trades that have shaped the 2009 Pittsburgh Pirate franchise. They include an impressive string which began with the acquisition of slugger Brian Giles in 1998. But, as is often the case in Pittsburgh these days, the Pirates are defined more by what has gone wrong then what has gone right, and the lasting impact of a couple infamous salary dumps is represented on this list as well.

5. Pirates trade Rajai Davis and Stephen MacFarland to the Giants for Matt Morris, 2007.

Ironically, the trade that sealed former GM Dave Littlefield's fate was actually one in which the Pirates took on salary. The Pirates agreed to take on all of Morris' contract, which amounted to a pro-rated $10 million in 2007 and $9.5 million in 2008.

The main player the Pirates gave up, Rajai Davis, does not even amount to a league-average hitter, but Morris was, to say the least, underwhelming for the Pirates, compiling an ERA of 6.10 in 2007 with the Bucs and an ERA of 9.67 in 2008 before being released.

This trade will forever live in Pirate infamy because fans pair the deal with the Pirates' decision to pass on highly rated catcher Matt Wieters in favor of mediocre pitcher prospect Daniel Moskos in the 2007 entry draft, pointing out that the money which went to Morris easily could have gone to Wieters instead.

4. Pirates trade Ricardo Rincon to the Indians for Brian Giles, 1998.

Almost certainly the best trade in Pirate history, and according to Rob Neyer perhaps the most lopsided trade in baseball history.

In four full seasons with the Pirates, Giles never had an OPS lower than .994 and never hit less than 35 home runs. He totaled 149 homers and 436 RBI in those four years. Rincon continued to be a solid left-handed reliever, but nothing more.

In 2003, as Giles was nearing the end of his prime, the Bucs dealt him to the San Diego Padres...

3. Pirates trade Brian Giles to the Padres for Jason Bay and Oliver Perez, 2003.

...for Bay, who almost immediately replaced Giles production in the middle of the Bucs' lineup. In 2004, his first full year in the majors, Bay hit 26 homers en route to being named the National League Rookie of the Year.

While Bay's production soared—he hit 30 or more homers in three of the next four years after his 2004 breakout—Giles' floundered. He remained an OBP machine, but his power disappeared almost immediately after leaving Pittsburgh. Giles hit 23 home runs in 2004 and then never hit more than 15 again in a season.

The Pirates also received flamethrowing left-hander Oliver Perez for Giles. Perez was one of the best pitchers in baseball in 2004, but has since struggled with control problems. In 2006, the Pirates dealt Perez and Roberto Hernandez to the Mets for outfielder Xavier Nady.

Bay lasted a bit longer with the Pirates, serving as the primary run producer in the Pittsburgh lineup until 2008...

2. Pirates trade Jason Bay to the Red Sox for Andy LaRoche, Brandon Moss, Bryan Morris, and Craig Hansen, 2008.

...when the Bucs dealt Bay to the Boston Red Sox as part of a three-way trade in which the Red Sox sent superstar Manny Ramirez to the Los Angeles Dodgers.

The trade, part of new General Manager Neal Huntington's efforts to add high-end talent to the system, netted the Pirates four prospects, three of whom have already spent time with the major league club.

After rough 2008 seasons, LaRoche and Moss have both emerged as everyday players (at least for the time being in Moss' case), but both have yet to live up to their power potential.

Hansen, a powerful reliever known for his slider, has struggled with control problems, and Morris, a high-upside pitching prospect, has had a poor season in the minors after returning from injury.

Meanwhile, Bay has had outstanding first half of 2009 in Boston, but it seemed unlikely he would ever reach his full potential while attempting to carry the Pittsburgh lineup.

The return from this trade—particularly the play of LaRoche and Morris—may very well define the Bucs' next five years.

1. Pirates trade Aramis Ramirez and Kenny Lofton to the Cubs for three players, 2003.

The other trades on this list may have a greater impact on the Pirates' play the next few years, but Pittsburgh fans will never forget the Aramis Ramirez trade.

Ramirez was 25 when the Pirates dealt him—an up-and-coming star at the third base position. It was one of the few times the Pirates dealt a player whose best years were clearly ahead of him.

Of the three players the Pirates received in the trade, the only decent prospect they received was Bobby Hill, who never lived up to his potential. One of the players they received, Jose Hernandez, was not a prospect but instead a veteran bench player.

Nothing is more emblematic of the Pirates' failure over the past two decades than the Aramis Ramirez trade.