MLB's 20 Worst Trades of the Last 15 Years

With the trade deadline days away, here are the 20 worst trades of the last 15 years.

20. The Los Angeles Dodgers trade Mark Grudzielanek and Eric Karros to the Chicago Cubs for Todd Hundley and Chad Hermansen (12/04/2002) – The Dodgers were tired of Karros and Grudzielanek fell out of favor with the manager. The front office felt it was better to move them and take on the salary of the corpse of Hundley. Hundley spent most of his time on the DL, while Karros and Grudzielanek his over .300 for the Cubs. Hermansen never developed into the hitter anyone thought.

19. The Houston Astros trade Willy Tavares, Jason Hirsh, and Taylor Buchholz to the Rockies for Jason Jennings and Miguel Asencio (12/12/2006) – Colorado, knowing that they couldn’t resign him, put Jason Jennings on the market. The Astros, fresh from running Andy Pettitte out of town and missing out on better pitchers, decided to go for broke. Broke was the key word, as Jennings spent most of the season on the DL, while the 3 new Rockies helped get them to the World Series. Asencio spent most of the season in the minors and became a free agent after the year.

18. The Boston Red Sox trade Cla Meredith, Josh Bard, and cash to the San Diego Padres for Doug Mirabelli (05/01/2006) – Boston traded back up catcher Doug Mirabelli after acquiring Bard from the Indians. The problem was Bard couldn’t catch Tim Wakefield’s knuckleball. Boston had to trade to get Mirabelli back, giving up more than what they dealt in the first place. Meridith was pretty good out of the bullpen while Bard is emerging as a starting catcher. Mirabelli was released by the Red Sox earlier this season.

17. The New York Mets trade Brian Bannister to the Kansas City Royals for Ambiorix Burgos (12/06/2006) – The Mets had a full rotation and needed help in the bullpen; the Royals were the opposite. Bannister was the odd man out in NY, after missing most of the previous season; when he did pitch, he was pretty good. Burgos was closer at one point for the Royals, but he could never over come his wildness. The swap was made and Bannister has been phenomenal while Burgos has seen little time in the Majors.

16. The Chicago Cubs trade Jon Garland to the Chicago White Sox for Matt Karchner (07/29/1998) – This cross town swap was a second thought for the White Sox. They were giving up a MLB reliever and were getting a struggling prospect. After being patient, the deal paid off. Garland broke out and was a star for the Sox during their World Series season, while Karchner faded quick.

15. The Arizona Diamondbacks trade Junior Spivey, Craig Counsell, Lyle Overbay, Chad Moeller, Chris Capuano, and Jorge de la Rosa to the Milwaukee Brewers for Richie Sexson, Noochie Varner, and Shane Nance (12/01/2003) – The Brewers were dumping Sexson because they knew they couldn’t afford him. The D’backs paid for, what they thought, was one of the missing pieces that would get them back to the playoffs. Instead, Sexson missed the full season. The Brewers used their pieces to help do nothing, but they still got more than Sexson was worth. Capuano even was a top pitcher for a season.

14. The Los Angeles Dodgers trade Paul Konerko and Dennys Reyes to the Cincinnati Reds for Jeff Shaw (07/04/1998) – The Dodgers needed a closer and gave up their best prospect for a declining one. Konerko would move on to become a solid MLB hitter, while Shaw struggled with closing out games and retired at a relatively young age (for a reliever).

13. The Pittsburgh Pirates trade Jason Schimdt and John Vaner Wal to the San Francisco Giants for Ryan Voguelsong and Armando Rios (07/30/2001) – The Giants gave up 2 guys who aren’t playing affiliated baseball for one of the most underrated pitchers, at that time. Schmidt wasn’t going to stay in Pittsburgh and his days in San Fran were pretty impressive (when healthy). Vander Wal was one of the top pinch hitters in the game, so he was a nice throw in.

12. The Toronto Blue Jays trade David Cone to the New York Yankees for Marty Janzsen, Jason Jarvis, and Mike Gordon (07/28/1995) – Cone was a good pitcher still at this point, so it was puzzling to see him traded, especially to a division rival. Cone would go on to have his career years in NY, while the 3 that the Blue Jays got did nothing.

11. The Florida Marlins trade Derrek Lee to the Chicago Cubs for Hee Seop Choi and Mike Nannini – Fresh off a World Series, the Marlins began to unload players that would have their salaries go up. Lee was one of the casualties. They received Choi, who was supposed to be the heir to Mark Grace; instead he couldn’t hit lefties and could barely hit righties. He made it half a season in Florida before being shipped to the Dodgers. Nannini never saw MLB action. Lee, on the other hand, has become a superstar.

10. The Toronto Blue Jays trade Michael Young and Darwin Cubillan to the Texas Rangers for Esteban Loaiza (07/19/2000) – Loaiza was an innings eater at this point; he would later be a much better pitcher, but way after the Jays had him. They gave up a future All Star Shortstop, something they have been searching for the last few years.

9. The Tampa Bay Devil Rays trade Bobby Abreu to the Philadelphia Phillies for Kevin Stocker (11/18/1997) – This move sums up the first 10 years of the Rays. Abreu was selected in the expansion draft (so Houston receives part of the blame for leaving him un-protected) and instantly traded to the Phillies for Stocker, who was supposed to be a decent player. Stocker didn’t last long in the league, while Abreu became one of the better hitters in baseball.

8. The Los Angeles Dodgers trade Pedro Martinez to the Montreal Expos for Delino DeShields (11/19/1993) – The Dodgers went throught a large period where they were in a win now mentality. The had the better Martinez brother still on the team and added a known commodity. Pedro would end up becoming one of the better pitchers of the last 20 years, dominating for the Expos, then the Red Sox.

7. The Seattle Mariners trade Derek Lowe and Jason Varitek to the Boston Red Sox for Heathcliff Slocumb (07/31/1997) – Slocumb was a decent closer at the time, while Lowe was stuggling through his rookie season. Varitek was the main part of the deal, although Seattle never saw him as the player he would become. Slocumb never pitched as well as he did the previous few seasons, while Lowe and Varitek became All Stars.

6. The Pittsburgh Pirates trade Aramis Ramirez, Kenny Lofton, and cash to the Chicago Cubs for Bobby Hill, Jose Hernandez, and Matt Bruback. (7/23/2003) – The NL Central was one of the tightest races in baseball this season, and the Cubs sealed it by stealing Ramirez and Lofton from the Pirates. Cardinal and Astro fans still wonder what pictures Jim Hendry had of the Pirates front office people. The Cubs would also get Randall Simon for nothing later on.

5. The San Francisco Giants trade Joe Nathan, Francisco Liriano, and Boof Bonser to the Minnesota Twins for A.J. Pierzynski (11/13/2003) – Pierzynski wore out his welcome in Minnesota; he was considered a club house cancer. The Giants needed a catcher and had thought they weren’t giving up much. Nathan was a struggling starter, Liriano was coming off a major injury, while Bonser was a top prospect. Nathan was thrown in the closer role after LaTroy Hawkins and Eddie Guardado walked. Bonser is currently a key set up guy after having on and off success as a starter. Liriano had an amazing 2006, dominating hitters before having another TJ surgery. AJ was traded after 1 season in San Fran.

4. The Oakland Athletics trade Mark McGwire to the St. Louis Cardinals for T.J. Mathews, Eric Ludwick and Blake Stein (07/31/1997) – The small market club trades it’s slugger, who they wouldn’t be able to sign. This was before Billy Beane was ravaging systems for prospects, so the A’s pretty much got nothing from the deal (Stein was moved later in the deal for Johnny Damon – that could be looked at as a bright spot). The Cardinals got a ton of revenue from McGwire’s home run circus, plus became a yearly playoff favorite.

3. The New York Mets trade Scott Kazmir and Jose Diaz to the Tampa Bay Devil Rays for Victor Zambrano and Bartolome Fortunato (07/30/2004) – I hear Daniels signing already. The Mets thought they could fix Zambrano’s mechanical problems; I don’t know how they thought they were upgrading the team by adding an under-performing starter for one of the top pitching prospects in the game. This was the begining of the end of the Steve Phillips Era.

2. The Arizona Diamondbacks trade Curt Schilling to the Boston Red Sox for Casey Fossum, Brandon Lyon, and Jorge de la Rosa (11/28/2003) – The Red Sox got their ace and all it cost them was a highly touted prospect and a couple of extra pieces. Of course, the prospect couldn’t stay healthy in his time in Boston (Fossum). Lyons have been alright when healthy in the closer role, but he’s not worth the price of Schilling. De la Rosa was traded shortly after this deal in the earlier mentioned Sexson deal.

1. The St. Louis Cardinals trade Dan Haren, Kiko Calero, and Daric Barton to the Oakland Athletics for Mark Mulder (12/18/2004) – Mentioning Mulder in St. Louis is like mentioning Zambrano in New York. Haren by himself would have been too much for Mulder, who hasn’t had a healthy season since coming to St. Louis (in fact, he’s attempting his third comeback this season and has only pitched 1/3 of a MLB inning). While the Cardinals wait to see if Mulder will ever pitch again, the A’s are sitting on a bounty from trading Haren with Barton their starting first baseman (Calero was recently released).

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