The 15 Worst Trades In MLB History

Since the very first days of baseball, general managers always want what other teams have. That led to trading and over the course of baseball history there have been some really bad transactions completed. It may be that one general manager is smarter than the other or has more information, or it could be just a case of getting lucky. But when a trade is made, it’s really hard to tell how it worked out until you take a look at it a couple of years down the road at least.

A lot of trades in today’s baseball are done because of money. The team no longer wants to pay a decent player what he is worth, for whatever reason they have. So they try to get fair value in prospects in return. Sometimes those prospects turn into gold, and sometimes they never amount to anything.

A beautiful example of this was when the Texas Rangers included Sammy Sosa, then a 21-year-old prospect, in a trade that sent Wilson Alvarez, Sosa, and Scott Fletcher to the Chicago White Sox for Harold Baines and Fred Manrique. At the time of the deal Baines was the key component. But after a few years with the White Sox and not doing very much, Sosa moved over to the other side of Chicago and became a major part of the Chicago Cubs lineup for many years. He topped 60 home runs in a season a few different times until he was caught cheating. But you can bet had the Rangers known that he was going to put up those numbers, they would have asked for a lot more than Baines and Manrique.

Here are 15 of the worst trades ever completed in baseball history.

15 Jeff Bagwell for Larry Anderson 


14 Randy Johnson for Mark Langston 


13 Jose Bautista for Robinson Diaz 

David Manning-USA TODAY Sports

12 Miguel Cabrera for Cameron Maybin and 5 others 

Rick Osentoski-USA TODAY Sports

This deal just doesn’t even make sense. In 2007 the Florida Marlins had a first baseman named Miguel Cabrera. He wasn’t a prospect as he had been with the team for 5 years and he was a slugger back then so they knew exactly what they had in him. But in the tradition of the Marlins franchise, good players must be traded. They sent Cabrera along with Dontrelle Willis to the Detroit Tigers for Cameron Maybin, Andrew Miller, Mike Rabelo, Dallas Trahern, Burke Badenhop, and Eulogio De La Cruz.

11 Keith Hernandez for Rick Ownbey and Neil Allen 


This trade was one of the keys that led to the New York Mets 1986 World Series championship. They got a perennial All-Star first baseman in Keith Hernandez from the St. Louis Cardinals in exchange for Neil Allen and Rick Ownbey, following the Cardinals 1982 World Championship season.

Hernandez, despite his on the field success, was having severe issues with then manager Whitey Herzog and after the Fall Classic he demanded to be traded. So Herzog thought he would get the last laugh by trading him to the Mets, a team that had just finished another horrible season. Hernandez initially refused to report to the Mets, but eventually changed his mind and he ended up getting the last laugh. He was one of the major pieces in the puzzle to turn the franchise around.

10 Mark McGwire for 3 players 


For the purposes of this article we are going to pretend that Mark McGwire never cheated. When the 1997 trade deadline was approaching, the Oakland A’s dealt McGwire to the St. Louis Cardinals, for Eric Ludwick, Blake Stein, and T.J. Matthews. The slugger was going to be a free agent after the season and the A’s just don’t like spending money. So they tried to get some kind of return on a player that had good value. It didn’t work.

Big Mac won the 1987 American League Rookie of the Year award by blasting 49 home runs and he helped the A’s win the World Series in 1988. He was also a nine-time All-Star while in Oakland, so you figure that the A’s were going to try to get all they could for him when it came time to deal him. They should have tried much harder.

The very next season McGwire hit 70 home runs with the Cardinals to break Roger Maris’ single season record as the baseball world looked on. He followed up that season with 65 more round trippers in 1999. During his 5-year stay in St. Louis he averaged 44 home runs per season and fans completely forgot about his time with Oakland.

9 Nolan Ryan for Jim Fregosi 


8 Pedro Martinez for Delino DeShields 


7 Pedro Martinez for Tony Armas and Carl Pavano 


Martinez won his first of 3 Cy Young Awards for his final season in Montreal. But the Expos couldn’t afford to keep him. So they tried to cash in and trade him away. It didn’t work. After the 1997 season they sent him to the Boston Red Sox for Tony Armas and Carl Pavano.

Martinez won 2 more Cy Young Awards in Boston and was the runner up on two other occasions. He was also the ace of the 2004 World Series Championship team. During his time in Boston he was one of the most dominant pitchers in the American League.

6 Dennis Eckersley for 3 minor league players 


5 Steve Carlton for Rick Wise 


4 Christy Mathewson for Amos Rusie 


In late 1900 the New York Giants pulled off one of the best trades in baseball history while the Cincinnati Reds got the short end of the stick by far. The Giants got Christy Mathewson for Amos Rusie. At the time Rusie had had a good career and was considered a star pitcher, but he hadn’t pitched in the previous two seasons because of a sore arm. His career was pretty much over. He pitched in three games for the Reds in 1901 and had a record of 0-1 before going back into retirement for good. One of the reasons reported for his decision to retire was marital issues.

3 Lou Brock for Ernie Broglio 


In mid 1964 the Chicago Cubs thought that Lou Brock had no place in major league baseball. So they tried to pull one over on their arch rivals, the St. Louis Cardinals, by trading them Brock for pitcher Ernie Broglio. Broglio pitched with the Cubbies for a little more than two years and put together a record of 7-19 before he retired. Mr. Brock however was a completely different story.

2 Frank Robinson for Milt Pappas and 2 others 


In 1965 the Cincinnati Reds said that Frank Robinson was beyond his best years. They said he was “an old 30” and traded him to the Baltimore Orioles for Milt Pappas, Dick Simpson, and Jack Baldschun. Pappas was the key get for the Reds and they certainly wish that they could get a do-over for the deal.

1 Babe Ruth for $125,000 

Baseball was in turmoil following the 1919 season with the scandal that took place in the World Series between the Chicago White Sox and the Cincinnati Reds. So it was a minor footnote when Boston Red Sox owner Harry Frazee sold Babe Ruth to the New York Yankees. After all, Ruth was mostly used as a pitcher by Boston and hadn’t yet started belting the ball out of the ballpark on a regular basis. Frazee sold the future slugger to the Yankees for $125,000 cash and a $300,000 loan so he could produce a Broadway show. Now that’s a lot of money by today’s standards in regular life, but not so much in the professional sports world. But in 1919 that was a TON of money and it was a move that buried the Red Sox for decades to come. In 1920 the Red Sox as a team hit 22 home runs while The Babe blasted 54 of them all by himself in New York. It was the beginning of a Yankee run that would see them win 27 championships and Ruth himself led the Bronx Bombers to 4 World Series championships and a total of seven pennants. The Red Sox would not win another World Series until 2004.


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The 15 Worst Trades In MLB History