What makes a deal a bad trade for one club has the potential to make it an all-time great deal for the other.
It’s those lopsided deals that make a deal spectacular or not, but there is more to it. To find the worst trade each MLB team has made, you need a few other qualifiers.
Did the players involved go on to have a Hall of Fame career? Did they help their new club win a championship? For the ones traded for him, how long did they last in their new city? In many cases, they didn’t even reach the major leagues. They were burnt-out prospects before even getting to the show.
Unfortunately for many teams, their worst trade is a detrimental move of embarrassment with the potential to get topped every time the general manager does execute a deal. Until that blockbuster dud is done, these are the worst trades in the history of every MLB team.
MLB worst trades: Where do we start?
Worst trade in Arizona Diamondbacks history: Curt Schilling to the Boston Red Sox
Spoiler alert! Curt Schilling is going to be on this list a couple of times. Frankly, every time he has been traded—five times total—the team moving him in the deal could be considered the loser.
On November 28, 2003, it was the turn of the Arizona Diamondbacks. They shipped him up to the Boston Red Sox for a haul of Mike Goss, Casey Fossum, Brandon Lyon, and Jorge De La Rosa. Schilling would finish second in the Cy Young race in 2004 while leading the league with 21 victories. He’d also help the Red Sox finally win a World Series.
Meanwhile, Goss never made the majors, Fossum had a 6.65 ERA in his one year with Arizona, Lyon was only an okay reliever, and De La Rosa was traded to the Milwaukee Brewers only a few days later. The Diamondbacks should have gotten much more for a guy like Schilling.
Worst trade in Atlanta Braves history: Dusty Baker to the Los Angeles Dodgers
The Atlanta Braves couldn’t have imagined how much success Dusty Baker would have even years after they traded him. Dealt to the Los Angeles Dodgers in November of 1975, Baker was a good young hitter for the Braves of the early 1970s. With the Dodgers from 1976-1983, he was even better.
The full trade Baker and Ed Goodson going to the Dodgers in exchange for Lee Lacy, Tom Paciorek, Jerry Royster, and Jim Wynn. None were particularly good in Atlanta.
In his second year with the Dodgers, Baker hit a career-high 30 home runs while slashing .291/.364/.512. He would also win the NLCS MVP that same year and eventually get a World Series ring with the club in 1981.
Worst trade in Baltimore Orioles history: Everything given up to acquire Glenn Davis from the Houston Astros
The January 1991 trade between the Baltimore Orioles and Houston Astros involving Glenn Davis is the worst ever made by the former of these two teams. A star during his seven seasons with Houston, Davis would suffer through injuries during his time with the Orioles. In parts of three seasons, he only appeared in 185 games for the team and hit just .247/.312/.400.
It’s what the Orioles gave up in this trade that makes it even worse. Steve Finley, Pete Harnisch, and our good friend of bad trades, Curt Schilling, were all involved.
Although Schilling’s best days were a little further into the future, Finley played exceptionally well for Houston and Harnisch was an All-Star in his first season with the club. He also continued to pitch well for the Astros for several more seasons, making this a deal fans in Baltimore would like to forget.
Worst trade in Boston Red Sox history: Selling Babe Ruth to the New York Yankees
Is there any question about what the worst trade the Boston Red Sox made is? No move in the history of sports may be more notorious than the 1919 sale of Babe Ruth to the New York Yankees.
Ruth wasn’t even traded for players. It was cash! The root of all evil turned the Yankees into a powerhouse club and began the Curse of the Bambino.
Until the Red Sox were able to win it all in 2004, they had to be constantly reminded of their owner’s misguided move. Although the curse has been broken, this is one of those trades, even more than 100 years later, you have to mention when talking about the worst moves ever made.
Worst trade in Chicago Cubs history: Lou Brock to the St. Louis Cardinals
Sure, it’s not quite up there with the Red Sox selling Babe Ruth to the Yankees but any deal between the Chicago Cubs and St. Louis Cardinals has the potential to be one where it’s tough to live down. This happened with the 1964 trade involving Lou Brock.
Brock was struggling at the time with the Cubs, batting .251/.300/.340 with 10 stolen bases in 52 games. Once dealt to the Cardinals, he reached a whole new level. He managed to slash .348/.387/.527 for them in his first 103 games for St. Louis. Add in 44 stolen bases and the iconic base thief we came to know was born.
Without diving too into what the players involved accomplished, we can already tell how much more this benefited St. Louis—the 1964 and 1967 World Series winners. Brock became a Hall of Famer and one of the best Cardinals ever. The Cardinals even picked up Jack Spring and Paul Toth in the deal for Ernie Broglio, Doug Clemens, and a near the end of his career Bobby Shantz. Brock, however, is the real prize.
Worst trade in Chicago White Sox history: Sammy Sosa to the Chicago Cubs
Why not stick with a theme and talk about rivals trading with each other? Although the two Chicago teams aren’t rivals on the field so much, their geographical location makes them competitors. In March of 1992, Ken Patterson was traded for George Bell of the Cubs. Oh and Sammy Sosa was involved in the deal, too.
Say what you want about Sosa. He may not have aged well in the history books due to his direct connection with the Steroid Era. However you may feel, there is no denying this was a huge win for the Cubs and even worse for the Chicago White Sox.
Sosa would hit 545 home runs with the Cubs after some big struggles with the White Sox. Bell would combine to hit 38 in his two seasons on the Southside before retiring.
Worst trade in Cincinnati Reds history: Christy Mathewson to the New York Giants
I’m going to guess you’re too young to remember Christy Mathewson. One of baseball’s first great pitchers of the 1900s, he spent a very short time with the Cincinnati Reds before getting traded to the New York Giants. He would eventually end his career there but not before winning 373 games and posting a 2.13 ERA with the Giants.
It’s bad enough to give up a Hall of Fame pitcher. But what the Reds got back in return makes it even worse.
The player they received in the deal was Amos Rusie. A fantastic pitcher in the 1800s, he made only 3 appearances for the Reds after the deal and pitched to an 8.59 ERA in those 22 innings. This might be the worst trade that we don’t talk about enough.
Worst trade in Cleveland Guardians history: Rocky Colavito to the Detroit Tigers
Whether they were the Cleveland Naps, Indians, or Guardians, the worst trade the Cleveland baseball franchise ever made has its own lesser curse. Rocky Colavito was a young stud outfielder fresh off of hitting a league-leading 42 home runs for the 1959 team. Then Cleveland decided to trade him on April 17, 1960.
It became known as the “Curse of Rocky Colavito.” The franchise had already been through a short championship drought with their last coming in 1948. As of 2022, they still haven’t won the big one again.
The player Cleveland received in the deal, Harvey Kuenn, spent just a single season in the city before he was traded away to the San Francisco Giants. Colavito bloomed further in Detroit prior to returning to Cleveland for the 1965 season. By this point, the curse was set and the worst trade in club history was done.
Worst trade in Colorado Rockies history: Nolan Arenado to the St. Louis Cardinals
The tale of this recent Colorado Rockies trade is far from over. We’re still only a few chapters into what the Nolan Arenado trade will ultimately become. However, the early indication is that the Rockies didn’t get much in return for one of the best third basemen in baseball.
The trade sent five players to the Rockies from the St. Louis Cardinals for Arenado. Still under contract through the 2027 season, he’s an investment the Cardinals decided to make for the present and the next few years before he inevitably begins to decline. Through one year, Arenado looks like he was worth it.
This is one of those trades that even if it doesn’t work out perfectly for St. Louis fans will remember with unkind words. It was symbolic to trade away Arenado shortly after signing him to a massive extension. Do the Rockies even want to win?
Worst trade in Detroit Tigers history: John Smoltz to the Atlanta Braves
In August of 1987, the Detroit Tigers traded a young pitcher named John Smoltz to the Atlanta Braves for veteran Doyle Alexander. Alexander had an incredible 11 starts for the Tigers in 1987, going 9-0 with a 1.53 ERA. Unfortunately, he was already in his late 30s and would spend only two more seasons in the big leagues.
Smoltz would make his MLB debut in 1988 with some sour results. Luckily, he had many more seasons ahead of him. He was an All-Star in 1989 as a sophomore and would end up winning 213 major league games—most of them with the Braves.
A member of the Cooperstown elite, Smoltz even managed to turn himself into a successful closer for several seasons following an injury. Maybe more impressive, he went back to starting and was great again! The trade may have helped the Tigers for one season. Smoltz helped the Braves for nearly two full decades.
Worst trade in Houston Astros history: Joe Morgan to the Cincinnati Reds
You can’t talk about the Big Red Machine Cincinnati Reds clubs without mentioning Joe Morgan. He arrived just in time for the fun via trade with the Houston Astros. When he joined the Reds, he became a superstar. He was the National League MVP in 1975 and 1976.
The full trade was not one you’d typically find a Hall of Famer involved in, especially when he already had a lot of years under his belt. Along with Morgan, the Astros included Ed Armbrister, Jack Billingham, Cesar Geronimo, and Denis Menke.
In return, Tommy Helms, Lee May, and Jimmy Stewart went to Houston. It was not a wonderful life for the front office when they saw what Morgan would become.
Worst trade in Kansas City Royals history: David Cone to the New York Mets and then to the Toronto Blue Jays
The Kansas City Royals had David Cone under their thumb for not one but two different tenures. After the 1986 season, they traded him and Chris Jelic to the New York Mets for Rick Anderson, Mauro Gozzo, and Ed Hearn.
Cone would begin his career with the Mets the very next season and in 1988, he was 20-3 with a 2.22 ERA. He’d continue to pitch successfully while the Royals didn’t get much from the players they acquired in the deal.
You could claim that was the worst Royals trade ever or pivot to the next time they traded Cone. After again acquiring him, the Royals said farewell in 1995 when they traded him to the Toronto Blue Jays for Tony Medrano, Dave Sinnes, and Chris Stynes. Only Stynes would ever even play in the major leagues.
Worst trade in Los Angeles Angels history: Dante Bichette to the Milwaukee Brewers
If you forgot about Dante Bichette’s time with the Angels—representing all of California at the time—don’t worry. You didn’t miss much.
Bichette began his career there but before the 1991 season, he was traded to the Milwaukee Brewers for Dave Parker. As great as he was in his prime, Parker was in the final season of his career and about to hit just .232/.279/.358 for the Angels in 501 plate appearances.
Bichette wouldn’t blossom until he joined the Colorado Rockies. Nevertheless, the Angels moved on from him too quickly and didn’t get much at all in return for a guy with some true 1990s power.
Worst trade in Los Angeles Dodgers history: Pedro Martinez to the Montreal Expos
Pedro Martinez got off to a promising start with the Los Angeles Dodgers in 1992 and 1993. So to see them trade him so quickly comes as a bit of a surprise. We know the stud he would end up becoming. Well before this occurred, the Dodgers decided to move on.
The future three-time Cy Young winner was traded in exchange for a single player, Delino DeShields. He was a below-average second baseman for the Dodgers during his three seasons with the team, mostly providing them with some speed and decent OBP numbers.
Compared to Martinez, DeShields doesn’t come close. To think the Dodgers had so many young stars during the decade and still managed to trade Martinez away before reaching his prime.
Worst trade in Miami Marlins history: Trading Miguel Cabrera to the Detroit Tigers
The Miami Marlins have made some massive blunders with trades. After both of their World Series wins, they went into sell mode. One player who stuck around a little longer was Miguel Cabrera. A rookie back in 2003, the Marlins didn’t trade him until after the 2007 season.
Cabrera had already become one of the league’s best hitters and he was about to get even better. Now a member of the 500 home run club and bound for the Hall of Fame, he’s going to go into Cooperstown with over 3,000 hits as well and a batting average over .300.
Trading him for just about anything didn’t make much sense but as the Marlins do, it was time to rebuild. Along with Dontrelle Willis, Cabrera headed to Detroit for Dallas Trahern, Burke Badenhop, Frankie De La Cruz, Cameron Maybin, Andrew Miller, and Mike Rabelo. None became stars with the fish.
Worst trade in Milwaukee Brewers history: Nelson Cruz and Carlos Lee to the Texas Rangers
On July 28, 2006, the Milwaukee Brewers sent two sluggers to the Texas Rangers for Julian Cordero, Francisco Cordero, Kevin Mench, and Laynce Nix. Those two sluggers were Nelson Cruz and Carlos Lee.
None of the players the Brewers got had particularly good careers with the team. Lee was tremendous down the stretch in 2006, slashing .322/.369/.525 with 9 home runs in his 59 games.
The real loss came when Cruz developed into such a powerful hitter. Although it would take until 2009 for him to reach double digits in home runs, he has been one of MLB’s most consistent home run hitters in the years since.
Worst trade in Minnesota Twins history: Johan Santana to the New York Mets
The Minnesota Twins did their best to compete in the early and mid-2000s with a relatively low payroll. One member of the organization during this time was star pitcher Johan Santana, the 2004 and 2006 Cy Young winner. A key part of their success, the Twins sent him to the New York Mets prior to the 2008 season.
The trade benefitted the Mets greatly and they made it better when they immediately signed him to an extension. In return, Minnesota got Carlos Gomez (before he was good), Deolis Guerra, Philip Humber, and Kevin Mulvey. Even if you watched the Twins from a distance, you know they lost this deal.
This trade was another one of those symbolic ones as well. Santana had more to give and at the time of the trade there were no injury concerns. He’d go on to become a beloved member of the Mets and even pitched the first no-hitter in franchise history. The Twins were left with practically nothing.
Worst trade in New York Mets history: Tom Seaver to the Cincinnati Reds
Sure, the New York Mets may have won the trade for Johan Santana but many years earlier they were the epic losers in a deal involving a man known as “The Franchise,” Tom Seaver. At the 1977 trade deadline, the Mets shipped him to the Cincinnati Reds in what became known as the “Midnight Massacre.”
The Mets were going into full rebuild mode and willing to part with the greatest player in franchise history. It became an epic debacle. The franchise wouldn’t be the same for several more years.
The Mets did get some quality in the deal, receiving four players total. Doug Flynn, Steve Henderson, Dan Norman, and Pat Zachry was the haul. For any of the good they were able to provide the Mets, it hardly made up for the lack of Seaver on the roster.
Worst trade in New York Yankees history: Trading Fred McGriff to the Toronto Blue Jays
Although Jay Buhner for Ken Phelps was bad, I think the 1982 trade involving Fred McGriff was worse. McGriff is about as borderline of a Hall of Fame player as you can get and probably should have a place in Cooperstown.
The New York Yankees decided to trade him, Dave Collins, Mike Morgan, and cash to the American League East rival Blue Jays for Tom Dodd and Dale Murray. Please take a moment and try to remember any of those great Dodd and Murray highlights in the Bronx.
McGriff would go on to have a long and storied career, smashing 493 home runs in parts of 19 seasons. None of those round-trippers would take place as a member of the Yankees.
Worst trade in Oakland Athletics history: Mark McGwire to the St. Louis Cardinals
Please allow me to be somewhat biased here. As someone who grew up with a dog named McGwire, I have to admire him a little more than the average athlete. Mark McGwire was my childhood hero. Looking back all of these years later, I’m amazed at how little the Oakland Athletics got in return for him from the St. Louis Cardinals.
Already one of the league’s top sluggers, McGwire was dealt in the middle of the 1997 season from Oakland to St. Louis in the worst trade the former ever made. The very next season, McGwire would hit 70 home runs and make even my mother and sisters fans for a summer.
As falsified as many of those dingers may have been, it doesn’t take away from how epically bad this trade was for the Athletics. All they got back was Erick Ludwick, T.J. Mathews, and Blake Stein. Ludwick and Stein barely had major league careers. Mathews stuck with Oakland for a while but was a 4.78 ERA reliever—hardly the impact player Big Mac was.
Worst trade in Philadelphia Phillies history: Ryne Sandberg to the Chicago Cubs
Ryne Sandberg and Larry Bowa to the Chicago Cubs for Ivan de Jesus. Philadelphia Phillies fans know exactly what this means.
This was the worst trade the franchise ever made. While moving on from Bowa may have brought about some sentimental anger, it was what Sandberg would become that makes this a horrific trade. Sandberg ended up winning the 1984 National League MVP and piecing together a Hall of Fame career—all but his first 13 big league games as a member of the Cubs.
In Philadelphia, de Jesus hit .249/.319/.319 in parts of three seasons. How a player could manage to have an OBP match his slugging percentage over this period of time is frightening. What makes this trade even worse is that de Jesus was fresh off of hitting .194 in 1981 when the trade was made. The Phillies should have known better than to give up anything promising for him.
Worst trade in Pittsburgh Pirates history: Aramis Ramirez to the Chicago Cubs
What is it with Pennsylvania baseball teams making bad trades with the Chicago Cubs? This one might not involve a Hall of Fame player but it still stings because of the rivalry between the Cubs and Pittsburgh Pirates.
In mid-2003, the Pirates sent star third baseman Aramis Ramirez and outfielder Kenny Lofton along with some cash to the Cubs. They received Mike Bruback, Jose Hernandez, and Bobby Hill in the deal. The Cubs weren’t even kind enough to include any propane or propane accessories.
Ramirez was already an established slugger at this point. However, with the Cubs, he was even better. He would go on to hit 239 home runs for them while batting .294. The well-traveled Lofton was a more minor part of the deal but he did bat .327/.381/.471 in 236 plate appearances for the Cubs. That certainly counts for something and helps make this an even worse deal.
Worst trade in San Diego Padres history: Ozzie Smith to the St. Louis Cardinals
Baseball fans of a certain age might not even believe Ozzie Smith ever played for a team other than the St. Louis Cardinals. It happened. His career began with the San Diego Padres. It was with the Cardinals he would grow as a hitter and become one of those rare baseball stars known for their defense.
The 1981 trade that sent Smith from San Diego to St. Louis involved a lot of players to be named later. By the time all of the paperwork was complete, it included Smith, Steve Mura, and Al Olmsted going to the Cardinals for Sixto Lezcano, Garry Templeton, and Luis DeLeon.
Templeton was probably the biggest addition the Padres made but his batting average dropped more than 50 points during his time in San Diego. The Cardinals received a legend in this trade. The Padres only got a few helpful pieces.
Worst trade in San Francisco Giants history: George Foster to the Cincinnati Reds
The Cincinnati Reds of the 1970s were a team built, in part, through some great trades. One of the early deals they made was the 1971 swap with the San Francisco Giants for George Foster.
The Reds landed the future MVP in exchange for Frank Duffy and Vern Geishert. Duffy would play only 21 games for the Giants and hit .179 in 1971 before joining the Cleveland Indians and being a mostly forgettable player. Geishert never played in the major leagues again.
Surrounded by talent, Foster was on his way to a great career full of home runs. Although he started slow, he would belt 52 home runs in 1977. From 1976-1978, he was the National League leader in RBI. The Giants definitely wish they could have this trade back.
Worst trade in Seattle Mariners history: Derek Lowe and Jason Varitek to the Boston Red Sox
A lot of the trades on this list were bad because of one player involved. This one is a little different. The worst Seattle Mariners trade involves two young players they gave up for a reliever.
At the 1997 trade deadline, Heathcliff Slocumb was traded from the Boston Red Sox to the Mariners. For the rest of the season and into the following year, he would go 2-9 with the M’s and pitch to a 4.97 ERA.
One only needs to mention the names the Mariners gave up to understand why this was so bad. Derek Lowe and Jason Varitek began their Red Sox journey. Both were core members of the 2004 Red Sox run to the World Series. Varitek would become a Boston-lifer, spending every major league game of his career with the club through the 2011 season and two championships.
Worst trade in St. Louis Cardinals history: Steve Carlton to the Philadelphia Phillies
Do teams never learn? You don’t trade star pitchers too soon even if you think the player you’re getting back is better. This is what happened when the St. Louis Cardinals swapped Steve Carlton for Rick Wise in 1972.
Carlton wasted no time making this a miserable trade for the Cardinals. On a horrific 1972 Phillies team, he won 27 games. The year would also end with him receiving his first of four Cy Young awards.
Wise would perform well for the Cardinals in his two seasons with the club yet that’s precisely the problem! He only spent two years there while Carlton spent far longer in Philadelphia and managed to help lead them to the 1980 World Series.
Worst trade in Tampa Bay Rays history: Bobby Abreu to the Philadelphia Phillies
Bobby Abreu was taken by the Tampa Bay Devil Rays in the 1997 expansion draft yet he never really got to get comfortable with the club. That same day, he was traded to the Philadelphia Phillies for shortstop Kevin Stocker.
Stocker would hit .250/.329/.347 in his 804 plate appearances for Tampa Bay. Abreu would do much more for the Phillies and beyond.
Starting in 1998, Abreu was the starting right fielder in Philadelphia. He hit over .300 and showed some power and speed. This would be a trend throughout his long career with every team he suited up for. Tampa Bay picked right then made the mistake of trading Abreu far too soon.
Worst trade in Texas Rangers history: Trading Alex Rodriguez and his huge contract away for not very much in return from the New York Yankees
I suppose signing Alex Rodriguez to his massive contract was the first mistake the Texas Rangers made. It was a somewhat foolish errand when they could have allocated the money to several different places instead of just one star player.
Rodriguez played well for him but it apparently wasn’t a match. So in February of 2004, they traded him to the New York Yankees for Alfonso Soriano and Joaquin Arias. A-Rod would continue to put up massive numbers while with New York.
Down in Texas, Arias played only 91 games in parts of four seasons, never once hitting a home run for the team. Soriano was a power-hitting second baseman but not much more. Texas would end up trading him after two seasons to the Washington Nationals for Armando Galarraga, Termel Sledge, and Brad Wilkerson. Even all of those players combined don’t match
Worst trade in Toronto Blue Jays history: Roy Halladay to the Philadelphia Phillies
When you trade a guy like Roy Halladay, you better get something good in return. Possibly the last great workhorse of Major League Baseball, the Toronto Blue Jays traded him to the Philadelphia Phillies in December of 2009.
Halladay would win a Cy Young the very next year and finish second the following season, too. He managed to toss a perfect game and no-hitter that same year.
All it took for the Phillies to land him was a package of Travis d’Arnaud, Kyle Drabek, and Michael Taylor. Only Drabek ever played even an inning for the Blue Jays. His 5.27 ERA with them answers why this is the worst trade the Blue Jays ever made.
Worst trade in Washington Nationals/Montreal Expos history: Randy Johnson to the Seattle Mariners
The Washington Nationals have made some bad trades. They haven’t been around long enough in their current incarnation, however, for us to confidently label any as their worst. To find that, we have to go back to their Montreal Expos days.
Randy Johnson was incredibly wild in the early part of his career with the Expos. In mid-1989, the team decided to send him to the Seattle Mariners in a rare May trade. Gene Harris and Brian Holman would join him. The Expos received Mark Langston and Mike Campbell.
Langston pitched well but he was only a rental for the rest of 1989. Meanwhile, Johnson became one of the most feared lefties in our lifetime.