10. Tigers Get Carlos Guillen; Mariners Get Ramon Santiago, Juan Gonzalez
Guillen's talent came out of nowhere when he got to the Tigers. His OPS+ was 142, 38 points higher than any previous season. He also hit 20 home runs after having just 29 home runs in three-and-a-half seasons with the Mariners.
Santiago played 27 games in two seasons with Seattle, later returning to the Tigers.
Juan Gonzalez isn't the Juan Gonzalez you're thinking of—not the one with 434 home runs. This Juan Gonzalez never got out of the minors.
Basically the Mariners traded a three-time all-star for 27 games.
9. Red Sox Get Curt Schilling; Diamondbacks Get Cassey Fossum, Brandon Lyon, Jorge de la Rosa, Michael Gross
The D-Backs were desperate to shed payroll after 2003, but they couldn't have received a more terrible package for Schilling.
Heralded as the "lefty Pedro Martinez" coming out of the minors, Fossum had a 6.65 ERA in Arizona, with a 1.65 WHIP and 31 home runs given up.
Brandon Lyon had a couple solid years as a relief pitcher for the D-Backs, but he wasn't worth Schilling.
Arizona might as well have traded Schilling for Lyon straight-up, since he was the only player that was somewhat worth having.
9b. Diamondbacks Get Curt Schilling; Phillies Get Omal Daal, Vincente Padilla, Travis Lee, Nelson Figueroa
Seems appropriate that this trade is included as well.
The Phillies handed Arizona a championship and the only semi-decent player they got in return was Vincente Padilla.
In the next two years, Schilling won 45 games, striking out 609 batters.
8. Athletics Get Dan Haren, Daric Barton, Kiko Calero; Cardinals Get Mark Mulder
This is vintage Billy Beane. Mulder was sold at his highest value, coming off four consecutive 15-win seasons.
Not only did the A's get Dan Haren, but they also got six prospects in return for Haren in 2008, giving the A's arguably the best farm system in baseball.
Mulder was only able to stay healthy one year for the Cards. He was pretty good too, sporting a 3.64 ERA in 2005. But Mulder only started 21 games after that season.
7. Cubs Get Aramis Ramirez, Kenny Lofton; Pirates Get Bobby Hill, Jose Hernandez, Matt Bruback
Ramirez has hit 25 home runs every year since arriving in Chicago. Not to mention he's had an OBP over .350 every year since then.
Although Lofton would have been of no use to the Pirates, he had an OPS+ of 120 in his 56 games with the Cubs.
The Pirates received a minor leaguer, a guy with a Spanish-sounding name, and a character from "King of the Hill" in return.
6. Orioles Get Adam Jones, George Sherill, Chris Tillman, Kameron Mickolio, Tony Butler; Mariners Get Erik Bedard
This may end up being the worse trade on the list in a couple years.
Bedard has struggled with injuries in Seattle, pitching only 15 games for the Mariners in 2008. He probably won't be healthy until May or June next year, too.
This leads to the likelihood that Bedard won't help the Mariners contend, and he won't even net them a compensation pick when he becomes a free agent after 2009.
The deal keeps looking better and better for the Orioles. Jones has star potential. Sherrill made the All-Star Game. Tillman is the top pitching prospect in a suddenly deep Orioles farm system.
5. Padres Get Adrian Gonzalez, Chris Young, Termell Sledge; Rangers Get Adam Eaton, Akinori Otsuka, Billy Killian
Not only could the Rangers have had Gonzalez, but they could have had a rotation of Young, Edinson Volquez, John Danks, and Armando Gallaraga.
Eaton pitched 13 games for the Rangers. Killian never made the majors. Otsuka was a solid relief pitcher for Texas for two years.
Gonzalez went on to become one of the only hitters who could ever put up good numbers in Petco Park.
Young has maintained an ERA under four in every season with the Padres.
4. Devil Rays Get Scott Kazmir, Jose Diaz; Mets Get Victor Zambrano, Bartolome Fortunato
The worst trades are usually the ones that don't make sense at the time. And I wouldn't say trading your first-round pick for someone who had a career WHIP around 1.50 is very smart.
Zambrano played three games with the Mets in 2004. He only pitched one full year with the team after that.
Kazmir was New York's aforementioned first-round pick in 2002. He dominated High-A ball the year he was traded from the Mets at the age of 20. Now he's only 24 and he's one of the best young pitchers in the game, with a career ERA of 3.61.
3. Giants Get Jason Schmidt, John VanderWal; Pirates Get Armando Rios, Ryan Vogelsong
Over the past 10 or 15 years, the Pirates have made countless trades that involved giving up their best players and getting almost nothing in return.
This one tops them all.
In 2003 and 2004, Schmidt was as great as any pitcher in baseball and he was still pretty solid until the Giants let him go after 2006.
Rios and Vogelsong only had one complete season with the Pirates.
2. Twins Get Joe Nathan, Francisco Liriano, Boof Bonser; Giants Get AJ Pierzynski
This move was heavily criticized by many Twins fans when it occurred. But like practically every trade on this list, it left everyone surprised.
With the Giants, Pierzynski was a very unpopular teammate. If that's not enough, he also threw out less than 25 percent of baserunners and had his lowest career OBP and slugging percentage.
Nathan hasn't had an ERA above 2.70 in any year with the Twins. At 24, Liriano pitches like an ace when healthy.
To show just how great a trade it was for the Twins, letting go of Pierzynski made room for Joe Mauer at catcher.
1. Indians Get Grady Sizemore, Cliff Lee, Brandon Phillips, Lee Stevens; Expos Get Bartolo Colon, Tim Drew
Considering the circumstances, you can't exactly blame Expos GM Omar Minaya for making this trade. There was a possibility of the Expos franchise discontinuing after the season and the Expos were contending for a playoff spot.
The Expos ended up missing the playoffs that year, even though Colon went 10-4 with a 3.31 ERA.
However, it ended up not being worth sacrificing what they could have had in the future: a five-tool superstar, the 2008 AL Cy Young winner, and one of the best all-around second baseman in the game.
Congrats, Minaya. You have committed the worst trade of the century.