Worst Trades in Major League Baseball History

[Casey Fisher]

This is for you baseball fans out there...

Nords, the Mariners were on the good end and the bad end of some of these trades... Roops, you must still be sick about the day that the Dodgers traded away Pedro... Anyways, this post is fairly long, but definitely worth reading. It's fun to look back and say, "WHAT WERE THEY THINKING???".

The Worst Trades in Baseball History. In no particular order...

January 10, 1991 – The Baltimore Orioles trade pitchers Curt Schilling, Pete Harnisch and outfielder Steve Finley to the Houston Astros for First Baseman Glenn Davis.
Despite his talent, the Orioles had found Schilling to bee too inconsistent and thus found it in their hearts to trade him. While Schilling wouldn't be all that great with the Astros, this trade is important because it was in Houston that Schilling received the right mental push to harness his talents (courtesy of Roger Clemens). Schilling live up to his potential by playing in three World Series (and winning two) and obtaining baseball immortality when pitching on a bad ankle. He remains one of the most dominant right handers in baseball. Harnisch would become a good middle of the rotation pitcher for the Astros. Finley would become a solid centerfielder, having some nice seasons in Houston and San Diego before he became one of the cornerstones of that 2001 Arizona Diamondbacks team. As for Davis? He would never be the same player for the Orioles as he was with the Astros. A week after the trade, he would get his jaw broken in a bar room brawl. After that, his numbers slowly dropped into obscurity.

August 30, 1990 – The Boston Red Sox trade first baseman Jeff Bagwell to the Houston Astros for pitcher Larry Andersen.
Figuring that they were just one piece away from making a return to the World Series, the Red Sox sought to firm up their bullpen by dealing for Anderson, who would pitch (not very well) in just 15 games for the BoSox before signing with San Diego the following year. Peter Gammons said shortly after the trade was made saying the Red Sox just traded away a future batting champion. History has since proven Gammons right, as Bagwell would become one of the two rocks of the Astros franchise for the next fifteen years, winning the Rookie of the Year in 1991, and Gold Glove and an MVP award in 1994.

July 25, 1910 – The Cleveland Naps trade outfielder Bris Lord to the Philadelphia Athletics for outfielder Joe Jackson.
This goes to show you that stupidity is not just a modern trend. The Athletics played Jackson for a total of TEN!!!! Games before they gave up on him. Lord was fine for a season and a half before he fell apart. As for Jackson, he became arguably the greatest pure hitter in baseball history…before tragedy would destroy his career in 1920.

July 31, 1997 – The Seattle Mariners trade pitcher Derek Lowe and catcher Jason Varitek to the Boston Red Sox for closer Heathcliff Slocumb
What the heck were the Mariners’ thinking? Okay, let me breath deeply and check the stats.
Okay, Slocumb was a fairly good closer in his career. Seattle, who was at the time dog fighting with the Anaheim Angels for control of the American League West., needed to shore up their bullpen if they were to make a run. While the trade paid off in the short term, after 1997, Slocumb was terrible. As for the other two, Lowe would switch from a good closer to a good starting pitcher and Varitek would evolve into the best catcher in baseball. More importantly, Seattle gave Boston the seeds that bloomed into their 2004 World Series title. Boston, send Seattle your thanks.

July 29, 1989 – The Texas Rangers trade pitcher Wilson Alvarez, outfielder Sammy Sosa and infielder Scott Fletcher to the Chicago White Sox for outfielder Harold Baines and infielder Fred Manrique.
This deal is undoubtedly the worst trade of all time for the Texas Rangers. The Rangers were trying to get some middle lineup support and thought Harold Baines, who was productive and seemingly ageless, could provide it. Not only would Baines and Manrique flounder so badly that both would be gone the following year, Alvarez would pitched a no-hitter in his first start for the Sox and would come back to haunt the Rangers in 1993. Alverez went 15-8 with an ERA of 2.95 and without him, the Rangers would finish second in the American League West to the eventual winners…Alverez’s new team, the Chicago White Sox. A further insult to injury would be trading Sosa, who the Rangers expected to be a player who hit .280 with 20 home runs and 80 RBIs. Sosa wound up becoming a superstar. The deal would be mentioned again during the 2000 Presidential Campaign, when former Rangers owner George W. Bush called this "the biggest mistake of my adulthood."

May 25, 1989 – The Montreal Expos trade pitchers Randy Johnson, Gene Harris, and Brian Holman to the Seattle Mariners for pitchers Mark Langston and Mike Campbell.
Here’s a head scratcher, as the Expos got robbed in this deal. This deal couldn’t even be defended even if Langston, who in his defense was a pretty good pitcher, had remained in Montreal. As for Campbell, he would never play for the Expos. And in return, they gave up on a tall, young and control-plagued left-hander named Randy Johnson, who would blossom into the Hall of Fame pitcher we know he is today, and on Holman, who was a good pitcher in his short time in Baseball. Had the Expos kept Johnson, they would have had one of the best one-two punches with Johnson and Pedro Martinez. Lord have mercy.

June 15, 1964 – The Chicago Cubs trade outfielder Lou Brock, pitchers Jack Spring and Paul Toth to the St. Louis Cardinals for pitchers Ernie Broglio, Bobby Shantz and outfielder Doug Clemens.
Five of the players exchanged never amounted to anything, while Brock became one of the all time greats in the game of baseball. Brock finished the last 16 years of his career with the Cards, winning two World Series, and was inducted into the Baseball Hall of Fame. It’s amazing to see how the droughts of the Cubs and the Red Sox were self inflicted some of the time.

June 15, 1977 – The New York Mets trade pitcher Tom Seaver to the Cincinnati Reds for pitcher Pat Zachry, infielders Doug Flynn, Steve Henderson, and prospect Dan Norman.
Known as the "Midnight Massacre" in New York, this trade dismantled the last remnants of the Amazin Mets of 1969. Also occurring that day was the trade of Dave Kingman, to the San Diego Padres for Paul Siebert and Bobby Valentine. Zachry would make the All-Star team in 1978, but would break his foot the next year and was never the same, Flynn was mainly a defender, Henderson would have one bit of glory as the runner up to Andre Dawson for Rookie of the Year and Norman was a bust. But the biggest lost was that the credibility that the Mets would lose in the eyes of their fans, as many remained angry with the team for years. As for Seaver, he would continue his Hall of Fame career with the Reds, having many more good seasons and winning 122 of his 311 wins away from the team.

July 21, 1988 – The New York Yankees trade outfielder Jay Buhner and prospects Rich Balabon and Troy Evers to the Seattle Mariners for first baseman Ken Phelps.
The Ken Phelps trade was symbolic of many of the Steinbrenner influenced trades of the era. Trade top young prospects for overpriced, declining stars. Phelps was a nice player, but was on the down side of his career when he was dealt to the Yankees. Phelps would last less than a season in New York while Buhner would become a star for the Mariners. This trade would also create one of the most famous Seinfeld lines, "How could you have traded Buhner for Ken Phelps?"

August 12, 1987 – The Detroit Tigers trade pitcher John Smoltz to the Atlanta Braves for pitcher Doyle Alexander.
A short sided trade. Alexander was brought in to help the Tigers make a run at the American League Pennant (which they would fall just short of by one game to the Red Sox.) Alexander would have one more good year in him before he tanked so badly in 1989 that he would retire. Smoltz, a Detroit native who wished he could stay and play for the home team, would make the majors the next year and would begin his Hall of Fame worthy career, becoming the ace pitcher that the Tigers sorely needed. Again, a terrible trade that benefited only in the short term, much like Terrell Owens deal for the Philadelphia Eagles (not that Alexander is in any way a terrible or crazy man.)

July 31, 1998 – The Houston Astros trade pitchers Freddy Garcia, John Halama and infielder Carlos Guillen to the Seattle Mariners for pitcher Randy Johnson.
The trouble with prospects is that you never know what you’re going to get. So you really can’t crack on teams on trades until much later, when said prospect blossoms for the new team. The best example I can name is when the New York Yankees traded Zach Day and Jake Westbrook for David Justice. Westbook looks good, Day is trying to hold on to a roster spot on the Nationals. But that’s a story for another day. In 1998, Seattle knew they had little chance of retaining Johnson, so they began to take offers for him, of which the Yankees and the Astros were chief bidders. The Yankees, after hearing the demand price, decided not to go for Johnson, but ensured that the Astros would pay dearly for Johnson. And they did. Halama and Guillen were average players, but Garcia became an ace for the Mariners for many years, before he got sent to the White Sox. As for Johnson, Johnson became the ace of the greatest Astros team in history, but he would leave for a big money contract with the Diamondbacks. Had Houston managed to keep Johnson, this trade wouldn’t be here.

November 19, 19993 – The Los Angeles Dodgers trade pitcher Pedro Martinez to the Montreal Expos for Delino DeShields.
A trade brought on by necessity. Because of second baseman Jody Reed rejecting the Dodgers’ offer of a contract extension to see what he could get on the open market (1 year, $750K, as compared to 3 years, $7.8 million.), the Dodgers were forced to bring in DeShields to patch up their infield. Pedro would dominate the National League and was a part of that magical 1994 Expos team that would have won the World Series before he became a part of the Red Sox. And the rest is history.

March 30, 1992 – The Chicago White Sox trades outfielder Sammy Sosa and pitcher Ken Patterson to the Chicago Cubs for outfielder George Bell
This is the second time Sammy Sosa is mentioned as far as trades go. In 1991, the White Sox finished second in the American League West. Figuring that they were one player away from making the post season, the White Sox dealt their prospect for the proven run producer Geroge Bell. What happened was that Bell was a disaster, not doing much better than Sosa. Meanwhile, Sosa blossomed into a superstar.

July 31, 1997 – The Oakland Athletics trade first baseman Mark McGwire to the St. Louis Cardinals for pitchers T.J. Matthews, Blake Stein, and Eric Ludwick.
This was highway robbery. Oakland, seeking to get McGwire’s deal off the books while at the same time obtaining young starting pitching, saw this deal as a way to help improve their rotation dramatically. Oh how wrong they were. Of the three, only Matthews would work out, and even he was mediocre, his best season coming in 1999 (9-5 with a 3.81 ERA). McGwire would energize the Cardinals, giving them a force in the lineup to go along with Jim Edmonds and Edgar Renteria, plus he’d keep the Cardinals the focus of attention in 1998 with his 70 Home Run season. This is one of the few trades that Oakland has done that hasn’t panned out as well as planned.

December 10, 1971 – The New York Mets trade pitchers Nolan Ryan, Don Rose, catcher Frank Estrada, and outfielder Leroy Stanton to the California Angels for shortstop Jim Fregosi.
The Mets thought that Fregosi would be their answer to upgrade their infield. And they probably thought that they got away with a steal, including Ryan, a wild, but talented player, and a bunch of busts in the deal. Fregosi would do poorly in New York (yet would regain some respectability with the Texas Rangers.) As for Ryan, his issues cleared up in California, and he embarked on his journey down the path that would establish him as one of the greatest pitchers of all time.

December 11, 1959 – The Kansas City Athletics trade outfielder Roger Maris, first baseman Kent Hadley, and infielder Joe DeMaestri to the New York Yankees for pitcher Don Larsen, outfielder Hank Bauer, first baseman/outfielder Norm Siebern, and utilityman Marv Throneberry.
For much of the 50’s and 60’s, the Athletics might as well have been a farm system team for the Yankees, as a lot of talent seemed to get shuttled to New York from Kansas City. However, the A’s thought they were making a good deal here. They were trading a young player who had put up some nice numbers, but wasn’t projected to be a star, and would package him with a pair of busts. However, Maris would blossom into a star and did exceptionally well for the Yankees, even without the 61 Homer season not taken into account. As for what the A’s got in return, almost all were busts or aging players, with only Siebern doing well.

November 29, 1971 – The Cincinnati Reds trade infielders Lee May, Tommy Helms, and Jimmy Stewart to the Houston Astros for pitcher Jack Billingham, outfielders Ed Armbrister and Cesar Geronimo, infielder Denis Menke, and second baseman Joe Morgan.
In a deal panned by the Cincinnati press, the Reds picked up three big pieces of the Big Red Machine in Morgan, Geronimo, and Billingham. Thanks in large part of this trade, the Reds would run off ten straight winning seasons, five division titles, three National League Championships, and two World Series titles. In return, they would trade May, who had just come off of a 39 home run season. He remained productive, but wouldn’t be a superstar. Helms was average, and Jimmy Stewart would win fame and fortune in the movie It’s a Wonderful Life.

January 27, 1982 – The Chicago Cubs trade Ivan DeJesus to the Philadelphia Phillies for Larry Bowa and second baseman Ryne Sandberg.
Brought into replace the aging Larry Bowa, DeJesus lasted just three mediocre seasons in Philly before flaming out with the Cardinals. Bowa did nicely in Chicago until he finished his career in New York. The real steal for the Cubs here was Sandberg, the future Hall of Famer that did nothing but excel at his position.

November 18, 1997 – The Tampa Bay Devil Rays trade outfielder Bobby Abreu to the Philadelphia Phillies for shortstop Kevin Stocker.
After taking him from the Astros in the Expansion Draft, the D-Rays promptly traded Abreu to the Phillies for shortstop Kevin Stocker. Abreu became one of the premier outfielders in baseball, while Stocker fell apart quickly for the Devil Rays and traded to the Angels in 2000.

November 13, 2003 – The San Francisco Giants trade pitchers Joe Nathan, Francisco Liriano, and Boof Bonser to Twins for A.J. Pierzynski
Seeing Pierzynski as their last major piece needed for the championship, the Giants traded three pitching prospects for the catcher. However, the Twins didn’t tell the Giants about Pierzynski’s irritating personality. Pierzynski did well for the Giants, but clashes with teammates prompted the Giants to not bring him back. Meanwhile, Nathan is one of the best closers in baseball, Liriano looks like the second coming of Johan Santana and Bonser is coming along nicely, making Giants fans wonder what could have been.

December 10, 1982 – In a six player deal, the San Diego Padres trade shortstop Ozzie Smith to the St. Louis Cardinals for shortstop Garry Templeton.
Seeking an offensive upgrade at short, the Padres swapped Smith, who remained the quality player that he had been and would be throughout his career, for Templeton, who promptly self destructed once he was in a Friar’s uniform.

January 3, 1920 – The Boston Red Sox trade Pitcher/Outfielder George Herman “Babe” Ruth to the New York Yankees for Cash.
I think we all know how that went for Boston…

July 30, 2004 – The New York Mets trade pitcher Scott Kazmir and infielder Jose Diaz to the Tampa Bay Devil Rays for Bartolome Fortunato and Victor Zambrano.
The worst thing that could have happened to the Mets in 2004 was them winning. The team clearly wasn’t there yet and wasn’t about to make a run. Instead, they traded Kazmir, who they deemed to be too small to be a starting pitcher for Zambrano. Zambrano has been average at best while Kazmir has become the ace the Mets sorely needed….except for the fact that he’s doing it with Tampa.

[Jason Spoor]

November 19, 19993 – The Los Angeles Dodgers trade pitcher Pedro Martinez to the Montreal Expos for Delino DeShields.
A trade brought on by necessity. Because of second baseman Jody Reed rejecting the Dodgers’ offer of a contract extension to see what he could get on the open market (1 year, $750K, as compared to 3 years, $7.8 million.), the Dodgers were forced to bring in DeShields to patch up their infield. Pedro would dominate the National League and was a part of that magical 1994 Expos team that would have won the World Series before he became a part of the Red Sox. And the rest is history.

yeah - this one still stings. DD just never had that explosion that he did when he was with Montreal where he teamed up with Marquis Grissom to become the most dangerous 1-2 hitters in all of baseball.

I have one that I don't think was on the list.
Blue Jays send David Cone to Yankees for pitchers Marty Janzsen, Jason Jarvis and Mike Gordon (July 28, 1995)
The Yankees most recent dynasty began in 1995, and Cone was a key ingredient in the Pinstripers 1995 playoff push, going 9-2. During the next five seasons, the aging right-hander was a team leader, was named to the All-Star team twice, led the AL in wins with 20 in 1998, and compiled a 55-38 record. Oh, and he pitched a perfect game. None of the pitchers the Blue Jays acquired played in the majors.

[Casey Fisher]

Excellent addition Roops. Any time you get a stud player for minor leaguers who never even make it to the big leagues, you got yourself a pretty good deal...

[Mike Nordin]

I think the M's made out pretty good on a lot of those trades. Even the Randy Johnson trade wasn't so bad when you think that those guys made up the 116 win season.
On another note, I've alway loved two NFL teams, the Hawks and the Vikings. I know this is talking Football, but the one trade that will always haunt me is the Walker for about every Viking trade. Walker was a talented player, but he was one of the Jinx players that no matter where he went they were doomed to fail. And on the other side, the Cowboys (whom I hate right along with the 49'rs and the Bears) went on to win a couple Superbowls.
I think I just threw up a little.

[Casey Fisher]

You are right in that the M's got the better end more than the losing end...

That Vikings trade has to rank among the worst NFL trades of all-time.

[Mike Nordin]

Ya, that was when Bavasi was the General Manager of the Vikings.

[Casey Fisher]

LOL plu.