The 10 Worst MLB Trades of the Last 10 Years

Look, it’s easy to criticize a baseball team for trading away a top veteran or prospect at the deadline in exchange for a package of ranch sunflower seeds and some Big League Chew.

But one thing to remember is that not only is it easy, it’s fun, too.

Below are 10 horrible baseball trades that went down in the past decade. You’ll not only find a few head-scratchiers, but also a couple of what-the-hell-were-they-thinking’s and some you’ve-got-to-be-f’ng-kidding-me’s as well.

And don’t be afraid to point and laugh at the teams that made these following trade blunders.

Listed in chronological order:

July 19, 2000: Texas Rangers trade Esteban Loaiza to the Toronto Blue Jays for Darwin Cubillan and Michael Young.
The Blue Jays essentially made two mistakes regarding Loaiza. The first was trading him for a future stud (Young), while the second was letting Loaiza go a year before he won 21 games for the Chicago White Sox. The Rangers basically got a five-time All-Star and career .300 hitter for a pitcher the Blue Jays eventually got zero use from.

July 26, 2000: Philadelphia Phillies trade Curt Schilling to the Arizona Diamondbacks for Omar Daal, Nelson Figueroa, Travis Lee and Vicente Padilla.
The Phillies handed the Diamondbacks a World Series title in 2001 when they traded Schilling for multiple players at the 2000 deadline. After Schilling was dealt to the desert, he and Randy Johnson formed the best 1-2 punches in all of baseball and all the D-Backs gave up for Shill was a failed prospect (Lee), a journeyman reliever (Daal) and some guy named Nelson Figueroa. Padilla, a 2002 All-Star, was the only one that amounted to anything in Philadelphia, but injuries eventually sidetracked his career.

July 30, 2001: Pittsburgh Pirates trade Jason Schmidt and Jon VanderWal to the San Francisco Giants for Armando Rios and Ryan Vogelsong.
While Giants’ GM Brian Sabean is better known for a 2003 trade blunder (see below), he did fleece the Pirates in 2001. Schmidt became a Cy Young candidate after arriving in San Fran and he helped the G-Men get to the 2002 World Series. The two guys the Pirates got in return for Schmidt weren’t even top prospects at the time and are rumored to be working in the appliance section at Best Buy. (Note: I once worked in the appliance section at Best Buy. There’s nothing wrong with that. Check out Whirlpool’s products – they’re fantastic.)

June 27, 2002: Montreal Expos trade Grady Sizemore, Cliff Lee, Brandon Phillips and Lee Stevens to the Cleveland Indians for Bartolo Colon and Tim Drew.
Colon wasn’t bad for the Expos; in fact, he finished with an overall record of 20-8 with a 2.93 ERA in 2002. But it was essentially all for naught as the Expos failed to make the playoffs and Colon bolted via free agency for the White Sox the following year. Oh yeah, they also gave up a five-tool stud in Sizemore and a pitcher in Lee who just started for the AL in the 2008 All-Star Game. Had the Tribe not given up on Phillips so soon, this trade might have looked even worse.

July 29, 2002: Philadelphia Phillies trade Scott Rolen and Doug Nickle to the St. Louis Cardinals for Placido Polanco, Mike Timlin and Bud Smith.
Some don’t blame the Phillies for dealing Rolen at the 2002 deadline because the club was unlikely to be able to re-sign him that offseason. But then again, Philly could have made more of an effort, too. Rolen has been one of the best all-around third basemen in the league and in 2004 he helped the Cards make a World Series appearance thanks to a monster season (.314, 34 HR, 124 RBI). In fairness to the Phils, they landed one of the top prospects in Smith (he became the 18th rookie since 1900 to throw a no-hitter in 2001), but he failed to develop. And Polanco showed some decent pop, but he was eventually traded to the Tigers for Ugueth Urbina. (The same Uguteh Urbina who was arrested by Venezuelan authorities on a charge of attempted murder.)

July 23, 2003: Pittsburgh Pirates trade Aramis Ramirez and Kenny Lofton to the Chicago Cubs for Jose Hernandez, Matt Bruback and Bobby Hill.
Were the Pirates trying to complete one of the worst deals in baseball history when they made this trade? Since the Cubs acquired him, Ramirez has hit over 100 dingers and has averaged over .300 twice. He’s not the greatest defensive third basemen, but he’s given the Cubs’ lineup tons of pop and it’s amazing to think Chicago also got the always-productive Kenny Lofton and cash from this deal. The three prospects the Bucs got in return have done next to nothing in the big leagues.

November 14, 2003: San Francisco Giants trade Joe Nathan, Francisco Liriano and Boof Bonser to the Minnesota Twins for A.J. Pierzynski.
The first thing to note is that this wasn’t a deadline trade. But since it was one of the worst trades in MLB history, I couldn’t leave it off the list. The Giants were dying for a catcher to replace Benito Santiago, so they decided to part with promising reliever Joe Nathan, an improving AAA pitcher in Boof Bonser and a minor league nobody named Francisco Liriano to land former All-Star A.J. Pierzynski. As it turns out, Nathan developed into one of the best closers in the game, Bonser turned out to be a middle of the rotation starter and before he got hurt, Liriano looked like an ace in the making (and still might be). And Pierzynski? He batted just .272, was generally hated in the Giants’ clubhouse and then signed with the Chicago White Sox the following year. But the real crime is how San Francisco GM Brian Sabean still has a job after making a trade like this.

June 24, 2004: Kansas City Royals trade Carlos Beltran to the Houston Astros in a three-team deal, which also sent Octavio Dotel from the Astros to the Oakland A’s, Mike Wood and Mark Teahen from the A’s to the Royals and John Buck from the A’s to the Astros.
Beltran owned the 2004 NLCS after joining the Stros in late June. He tied Barry Bond’s single postseason record with eight home runs and also knocked in 14 RBI, scored 21 runs and also batted .435 to boot. Talk about leading the Astros to the promise land – he essentially carried Houston to a NLCS appearance, even though they eventually lost to the St. Louis Cardinals. To be fair, the Royals weren’t completely bamboozled in the deal. They did get two eventual starters in Teahen and Buck, and it was highly unlikely they were going to re-sign the free-agent-to-be Beltran following the year anyway.

July 30, 2004: The New York Mets trade Scott Kazmir and Joselo Diaz to the Tampa Bay Devil Rays for Victor Zambrano and Bartolome Fortunato.
This trade looks worse every year. The Mets were desperately trying to contend for a playoff spot in 2004, so they gave up their top-pitching prospect (Kazmir) for an already injured Zambrano, who went on to start just three games before winding up on the DL. Zambrano also missed the entire 2006 season after suffering a torn flexor tendon in his pitching elbow. Kazmir, meanwhile, continues to develop into one of the league’s best young pitchers and has given Tampa a bona fide ace. Imagine how good the Mets’ starting rotation would be with Johan Santana, Kazmir, John Maine and a healthy Pedro Martinez. (Assuming, of course, that the Mets would have still traded for Santana in 2008 if they had Kazmir on the roster.)

July 31, 2004: New York Yankees trade Jose Contreras to the Chicago White Sox for Esteban Loaiza.
Normally the Yankees are the ones fleecing other teams but in 2004, the fleecers got fleeced themselves. After just 27 starts, the Yankees grew tired of Contreras’s inconsistencies on the mound and sent him and cash to Chicago for Loaiza. The following year, Contreras finished 15-7 with 154 strikeouts and a 3.61 ERA. He was also the Sox’ Game 1 starter when they swept the Houston Astros in the 2005 World Series. As for Loaiza, he was so bad in New York that he was banished to the bullpen for the rest of the 2004 season and eventually signed with the Washington Nationals the following year.

Update: The following corrections have been made: The Houston Astros lost to the St. Louis Cardinals in the 2004 NLCS, not to the Boston Red Sox in the World Series. And Curt “Shilling” was corrected to Curt “Schilling.” Thank you for those of you who brought the mistakes to our attention.

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