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

15. Jeff Bagwell for Larry Anderson

In 1990 the Boston Red Sox needed pitching and they had an abundance of young stars in their system. Mo Vaughn was the Red Sox established first baseman and the team decided that Jeff Bagwell wasn’t good enough to learn a new position. So they traded the prospect to the Houston Astros for relief pitcher Larry Anderson. Anderson accomplished nothing in his career while Bagwell went on to a 15-year career that saw him hit 47 home runs and drive in 132 runs in 2000. He hit 449 career home runs and had 1,529 RBI as well. In 1991 he won the National League Rookie of the Year and he was a 4-time All-Star. He also added 3 Silver Slugger awards. If Boston only knew then what they know now.

14. Randy Johnson for Mark Langston

14. Randy Johnson for Mark Langston

Coming up on the trade deadline in 1989 the Montreal Expos were not happy with the way their young pitching prospectRandy Johnson was pitching. He was 0-4 on the season and had an ERA of over six. The previous year he had gone 3-0 with Montreal in 4 starts but his luck didn’t carry over to the new season. The Seattle Mariners sent Mark Langston and a prospect to the Expos for Johnson. Langston was a decent pitcher but he was nowhere near the dominant force that Johnson would become. He won 17 games or more in ten different seasons and had a career record of 303-166. He won five Cy Young Awards and a World Series while Langston only played a single season with the Expos.

13. Jose Bautista for Robinson Diaz

13. Jose Bautista for Robinson Diaz

Jose Bautista was 27 years old in 2008 when the Pittsburgh Pirates sent him to the Toronto Blue Jays for Robinson Diaz. Bautista had not done much in his career to that point so the Pirates had no idea of the potential that he had in him. But they sure found out after the trade as they watched him become a 6-time All-Star. In 2010 he became the first player in Toronto’s franchise history to hit 50 home runs in a single season. He has had six consecutive seasons of 20 home runs or more and Toronto landed him for next to nothing. Diaz played two seasons with the Pirates but got into only 43 games. Talk about hitting the jackpot!

12. Miguel Cabrera for Cameron Maybin and 5 others

12. Miguel Cabrera for Cameron Maybin and 5 others  

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.

Willis wasn’t a Hall of Fame pitcher but he wasn’t bad. Cameron Maybin has turned out ok at best and Badenhop is an average reliever. Cabrera meanwhile has hit 30 home runs or more 6 times since leaving the Sunshine State and he has topped 100 RBI’s seven different times. He has 408 career home runs and 1,445 RBI. Oh and he also owns a career batting average of .321. Cabrera is a definite Hall of Famer that the Marlins just weren’t able to cash in on.

11. Keith Hernandez for Rick Ownbey and Neil Allen

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.

Hernandez turned into a legend in Mets lore while Allen and Ownbey combined to do nothing in St. Louis. Allen was sold to the New York Yankees after failing miserably in St. Louis and Ownbey only started 7 games for the Cardinals. St. Louis fans are still mad about this trade and they have every right to be.

10. Mark McGwire for 3 players

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.

Ludwick, Stein, and Matthews never did much and the A’s definitely got the short end of the stick on this trade. It’s too bad that McGwire was cheating the whole time and made his outstanding career stats tainted.

9. Nolan Ryan for Jim Fregosi 

9. Nolan Ryan for Jim Fregosi

The New York Mets have made a lot of bad trades in their history but this one is probably the worst one ever. In 1971 they traded young pitcher Nolan Ryan to the California Angels for third baseman Jim Fregosi. At the time of the deal it didn’t seem like a bad trade as Ryan hadn’t yet found solid footing in the major leagues and Fregosi was an All-Star. Unfortunately for New York, Fregosi didn’t even last two seasons with the Mets while Nolan Ryan went on to a Hall of Fame career. Over his 27-year career he won 324 games, struck out over 5,700 batters, oh and he threw 7 no-hitters. Nobody in baseball history has thrown that many in a career.

8. Pedro Martinez for Delino DeShields

8. Pedro Martinez for Delino DeShields

In his first two seasons with the Los Angeles Dodgers, Pedro Martinez had a record of 10-6 with a pair of saves. After the 1993 season they could tell that he was a good pitcher but they obviously didn’t know how good. They traded him to the Montreal Expos for Delino DeShields. DeShields was an average base stealer and had good speed but no glove or bat. He lasted three years with the Dodgers before they traded him to the St. Louis Cardinals. Martinez instantly became a winning pitcher with Expos, posting a winning season in each of the four years he was there. His final year in Montreal he had a record of 17-8 and an ERA of just 1.90. So what did the Expos do? They traded him. Keep reading.

7. Pedro Martinez for Tony Armas and Carl Pavano

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.

Armas was a less than average pitcher in 8 seasons with the Montreal/Washington franchise. Pavano spent five years with the team and had one season that he went 8-4. Every other season with the team he posted a losing record.

6. Dennis Eckersley for 3 minor league players

 6. Dennis Eckersley for 3 minor league players

In 1987 the Chicago Cubs came to the conclusion that starting pitcher Dennis Eckersley was at the end of his career. So they traded him to the Oakland A’s, who had other plans for him. The Cubs received Mark Leonette, Brian Guinn, and David Wilder in the deal. None of those players ever reached the major leagues while Eck went on to become one of the game’s most dominant closers ever. Over the next 12 seasons he had 387 saves and in 1992 he won both the American League’s Cy Young Award and the MVP. Not bad for a guy that was deemed as having his career finished. He was voted into the Hall of Fame in 2004.

5. Steve Carlton for Rick Wise

5. Steve Carlton for Rick Wise

Steve Carlton was one of the best left handed pitchers of his time, but the St. Louis Cardinals had no idea what was ahead of him in his career. If they had known, they certainly wouldn’t have traded him to the Philadelphia Phillies for Rick Wise in 1972. Carlton won 27 games for the last place Phillies club and he notched an all time record 45% of the team’s victories. He also led the National League with a 1.97 ERA and had a league leading 310 strikeouts. He was voted into the Hall of Fame in 1984. Wise played only 2 seasons for the Cardinals and another 11 years in the major leagues, but he was no Steve Carlton by any means. Over his career he was no more than an average pitcher.

4. Christy Mathewson for Amos Rusie

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.

Mathewson won a total of 373 games in his career, winning 30 or more games in a season four different times. He was one of the first five players elected into the Hall of Fame. Rusie was elected into the Hall of Fame in 1977 but that was based on what he had accomplished prior to the trade happening.

3. Lou Brock for Ernie Broglio

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.

Over the next 15 years Brock led the Cardinals to a pair of World Series championships and one more pennant while collecting 938 stolen bases. He was voted into the Hall of Fame in 1985. Most Cub fans refuse to acknowledge that this trade ever happened.

2. Frank Robinson for Milt Pappas and 2 others

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.

In his first season with the Orioles, Robinson hit .316 and blasted 49 home runs and had 122 RBI to win the Triple Crown. He also led the Orioles to a pair of World Series championships, the second one coming against the Reds in 1970. He was named American League MVP and was voted into the Hall of Fame in 1982. Pappas spent a little more than 2 seasons with the Reds and put together a record of only 30-29 before being traded.

1. Babe Ruth for $125,000

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 soldBabe 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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