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.
Man wat that Expos trade bad…Montreal Expos trade Grady Sizemore, Cliff Lee, Brandon Phillips and Lee Stevens to the Cleveland Indians for Bartolo Colon and Tim Drew.
I’m a big Yankees fan, coz they are really professional baseball team! I used to attend their games just to see their professional plays. They have captivated millions of fans. And they are also the best-selling American team even their
God Bless you Rihanna…..finally another Yankee fan
Is Rihanna really Boston24??
Boston 24 is one his way to the Dodgers with Manny ……..
umm… beltran didnt get the stros to the world series
they lost in the NLCS to the cards
just thought I’d point out this glaring mistake
I’m still trying to figure out what Rihanna wrote……
Thank you, Matt – honest (and yes, glaring) mistake on my part.
My guess is Rhianna is from a foreign Country ……. Da Bronx. Somebody get her a red yankee hat and a subscription to the YES network … oh yeah and ask her if she ever heard of a Salary Cap.
What about Jay Buhner to The Mariners for Ken Phelps?
Frank Costanza
I think they should try to get Kevin Brown off the couch Dawg ……..
Mr Wilhelm
Yeah dude you got some good ones there. pretty bad trades for sure.
Jt
Ultimate Anonymity
Schilling. Not Shilling.
hmm now what the hell makes the bronx a foreign country you ignoramous
You forgot the Mark Mulder trade.
You can’t forget about the Sox getting Varitek and Lowe from the Mariners for Slowcumb
How about the Padres getting Chris Young and Adrian Gonzalez for Adam Eaton and Akinori Otsuka?
Yankees fans…what a long strange trip.
Actually you missed the worst trade of all, Jermaine Dye for Nefi Perez
Baseball is not even a decent sport. Gone are the days when most kids had to amuse themselves with a stick and a ball. No other sport in history had to sue a TV channel (ESPN) to keep their crap “sport” on TV.
I’ve gotta disagree on the Colon trade. It was certainly not even, and the Nationals/Expos franchise would be much better off had they not made it, but the trade was made at the time that MLB had announced that the Expos were going to be contracted. Omar Minaya (then Expos GM) had been told by his bosses that their team wouldn’t exist the following year. So why not trade a bunch of stud prospects you’re never going to get to play for a shot at a decent season? But as a Nats fan, I am seriously bitter we don’t have Lee, Phillips and Sizemore out there.
What about the Phillies trading Placido Polanco (currently batting over .300 for Detroit) to the Tigers for Ugueth Urbina (who is in jail in Venezuela for setting his farmhands on fire then attacking them with machetes) and Ramon Martinez (now with the Mets)?
The Colon trade was an incredible trade for the Indians, and it would have been better had the Tribe brain trust not given up on Phillips.
That said, Colon went on to win a Cy Young award. Of course he didn’t do it with the Expos/Nats, but it’s not like the Expos got crap back. So I don’t think it belongs on the list.
Ok, so you guys blew this… you didn’t even list thee WORST trade in baseball history.
Seattle trades Derek Lowe and Jason Varitek to the Boston Red Sox for Heathcliff Slocumb
I believe that was back in 97 or 98 so maybe more than 10 years ago
The Phillies only traded Polanco because he was blocking Chase Freakin’ Utley and was too whiny to play Third Base. Urbina would have been a useful bullpen arm past the 2005 season if he wasn’t some sort of sharecropping slaveowner from the 1850s, and there’s no reason to cry over Ramon “PTBNL” Martinez.
Pirates trade Stephen McFarland and Rajai Davis to the Giants for Matt Morris. Ok, on the cover it seems like the Pirates got a steal, they traded two nobodies for a major league pitcher and they needed pitching help. Oh wait, the Pirates had to pick up all of Morris’ $13 million left on his contract. After four years earlier being unable to afford Aramis Ramirez’s $15 million in ’04 and ’05, they trade for a pitcher who’s owed $13 for less than a season and a half. He didn’t even last to May of this year before management dumped him.
Wow, seems like the White Sox really like picking up the good free-agents after a “bad trade” year. Colon (9 CG and a Cy Young), Loiza (21 wins), Contreras (15 wins and a ring), and Pierzynski (career .285 BA and a ring), and now Chris Carter for Carlos Quentin is looking like a prosperous trade too. Maybe this offseason they’ll chase down Sheets or Sabathia or Penny, have them deliver for a year, then either lose them or die slowly for the following 3 years.
Uh…Boof Bonser is in the bullpen because of some very ineffective starts in the beginning of the 2008 season and is no longer in the Minnesota Twins starting rotation.
Uh…Boof Bonser is in the bullpen because of some very ineffective starts in the beginning of the 2008 season and is no longer in the Minnesota Twins starting rotation.
I get that. And his numbers haven’t been great since he joined Minnesota, but the Twins could have done worse than to add a starter (former starter now) in that trade. That’s all my point was.
As a long time Giants fan, I too have wondered how the heck Sabean has kept his job all these years. I realized it’s because the ownership checked out after the whole Bonds’ debacle. Now that Magowan has stepped down, Sabean should be gone after this year and with a rotation of Lincecum/Sanchez/Cain, they should be contending soon.
How did the Sox/Mariners trade not make this list? Sox get Varitek and Lowe for Heathcliff Slocum??? That has to rank up there as one of the most lopsided deals.
How did the Sox/Mariners trade not make this list? Sox get Varitek and Lowe for Heathcliff Slocum??? That has to rank up there as one of the most lopsided deals.
Chaz – That deal was made in 1997, therefore it missed the 10-year cut. You’re right though – that trade was brutal.
G Fan – I’m right there with you on the Giants. Their starting rotation is young and extremely talented, but Sabean has done nothing to build positional talent in the Giants’ farm system. It’s sad that Matt Cain loses every game 2-0…
what about Jeff Bagwell for Larry Anderson?
Julz says:
what about Jeff Bagwell for Larry Anderson?
I only did trades in the past 10 years…that one was in 1990, but it was definitely one of the worst of all-time.
My top 5 are:
- The Mets trading Kazmir for Victor Zambrano.
- The Expos trading Grady Sizemore, Brandon Phillips, and Cliff Lee for Bartolo Colon.
- The Giants trading Liriano, Nathan, and Bonser for Pierzinsky.
- The phillies trading Jason Schmidit for two low level prospects.
- The pirates trading Aramis, and Lofton for basically nothing.
- The Braves have three real good trades that are not in the list. The tigers trading John Smoltz for for Doyle Alexander of the Braves. Tim Hudson for Charles Thomas, Juan Cruz, Dan Meyer. And recently Jair Jurrjens and top outfield prospes Gorkys Hernandez for Edgar Renteria.
Tomas,
Ed Wade certainly was an awful GM, but he never traded Jason Schmidit (or Schmidt). Wrong team. Also Tomas, the article is on worst trades of the last 10 years. The John Smoltz trade happened over 20 years ago….
I agree. Loiza for contreras was a terrible trade. But Contreras iis injured now untill 2nd half of 09… hmmmmmm…
Kazmir for Zambrano will go down as the 2nd worst trade in mets history right behind the one that sent seaver to the reds
Re: Schilling trade: Omar Daal was NOT a journeyman RELIEF PITCHER. He was a journeyman STARTING pitcher, mostly. He actually had two pretty good seasons in AZ with a 2.88 ERA and 3.65 ERA in the years before the Schilling trade. But he never posted those kinds of numbers again.
Two other comments:
1) you claim that Vogelsong and Rios weren’t rated as very good prospects at the time of the trade for Schmidt, but I seem to recall that Vogelsong WAS regarded as a pretty good prospect at the time. I remember this trade well, being a rival DBacks fan, and my team was also looking for a starting pitcher that year. I believe we ended up with Albie Lopez, and at the time, I was pissed that we didn’t get Schmidt, which was the guy I thought we should have gone after instead. At least we won the World Series that year anyway, but could you imagine a rotation with Johnson, Schilling, AND Schmidt?
2) The trade of Karim Garcia for Luis Gonzalez AND CASH should probably have made your list!
“Kazmir for Zambrano will go down as the 2nd worst trade in mets history right behind the one that sent seaver to the reds”
It is tough to top the Seaver trade, but it will also be tough to top these other bad trades in Mets history:
– Amos Otis for some guy named Foy
– Nolan Ryan for an over-the-hill Jim Fregosi
– Rusty Staub for an over-the-hill Mickey Lolich
– Lenny Dykstra for Juan Samuel (although Dykstra’s drug issues came out later, making this trade a bit more understandable)
– Jason Bay + 2 others for 2 forgetable no-names
Just remembered another awful trade that was a head-scratcher AT THE TIME. No hindsight was needed to know this trade was going to be lopsided:
Jim Edmonds for Kent Bottenfield and Adam Kennedy
worst trade of all time:
Milton Bradley and Antonio Perez for Andre Either.
Great trade on Billy Beane to give up on a youngster like Either while neither Bradley or Perez lasted more than 1 calendar year in Oakland.
Now Either is a budding star for LA Dodgers.
What about Erik Bedard from the O’s to the M’s in exchange for Adam Jones George Sherill (who was recently traded for 2 prospects) and three minor league pitchers (most known of which Chris Tillman). Bedard Got hurt and was ou for the entire first season with Seattle then got hurt twice again this year. Jones and Sherill were both all-stars Tillman was ranked the 16th prospect on mlb.com top 50 prospects.
Orioles fan,
That’s a good one to bring up, although I wrote this a few months after that trade went down so I wouldn’t have known that Jones and Sherill would turn out to be All-Stars.
Hello…how bout my braves gave away Adam Wainwright ,Jason Marquis,and Ray King for jd drew……yea at the time drew was good but the braves should have known that he wouldnt re sign….so bad trade…….