The ideal trade scenario in every case is that the trade is fair and works out successfully for both teams. And this does actually happen sometimes. But it is much more likely that one team will do better than the other. And sometimes, one team does absurdly better.
Lopsided trades can happen for a number of reasons whether it’s bad scouting or the player just needed a change of scenery. Sometimes a team will overvalue their pennant chances. Other times, it’s worth it for a team to give up a potential star if they can win that year’s title. Below is a list of the most lopsided trades of all time.
1919- Babe Ruth To The Yankees
The most famous lopsided trade in baseball history is also one of its oldest. The story is well known. Babe Ruth was a 2-way star as an Outfielder and a Pitcher. But Red Sox Owner, Harry Frazee needed money to finance a theater production.
So the Sox owner sold Ruth to the hated Yankees and put on his show. The deal ended up paying off big for the Yankees. Ruth was a transcendent star who led the Yanks to 4 World Series and the Red Sox took 86 years to win their next one.
1966 – Frank Robinson To The Orioles
Despite many years of superstar production, the Reds thought Frank Robinson was getting long in the tooth. They traded the star to the Baltimore Orioles in 1966 for a package led by Milt Pappas. It turned out Robinson was far from done.
Robinson continued to be a major star for the Orioles and Pappas never quite reached his supposed potential. The Outfielder became the leader for a Baltimore team that would capture the 1970 World Series.
1972 – Nolan Ryan To The Angels
The Mets of the late 60’s and early 70’s had a pitching staff that boasted tremendous talent including Nolan Ryan. The team figured they had enough pitching talent with Tom Seaver and Jon Matlack. Beside, Ryan could barely hit the broadside of a barn.
Once he reached Los Angeles, though, Ryan began to harness his amazing stuff and became a superstar. He pitched for the Angels for eight seasons, made 5 All-Star games and recorded a boatload of strikeouts.
1982 – Ryne Sandberg To The Cubs
During the 1981 season, Philadelphia realized they had a raw prospect in Ryne Sandberg who didn’t necessarily have a position. Wanting to acquire a more veteran player, the Phillies traded Sandberg to the Cubs for Ivan De Jesus.
De Jesus was a decent fielding Shortstop with a light bat. Sandberg went over to Chicago, became a Second Baseman and an immediate superstar. Sandberg became a legendary player for the Cubs and was elected into the Baseball Hall of Fame in 2005.
1983 – Keith Hernandez To The Mets
Keith Hernandez was a star level player for the Cardinals in the late 70’s and early 80’s. While in St. Louis he won an MVP Award and a World Series title in 1982. The First Baseman got caught up in a drug scandal and was traded to the Mets.
He immediately slotted in as the leader for an up and coming Mets club. In 1986, Hernandez captained the Mets to the World Series title. The best player St. Louis received in return, pitcher Neil Allen, had an unspectacular career and was gone from the Cardinals by 1985.
1987 – John Smoltz To The Braves
Today, teams are wise about the potential disastrous results of trading a top prospect for anything less than a star player. In 1987, there was less thought put into it and the Tigers traded John Smoltz to the Braves for Doyle Alexander.
Alexander pitched like a star for the Tigers down the stretch, but faded after that and was out of the league by 1990. Smoltz became a star for the Braves, winning a Cy Young, a World Series, and making the Hall of Fame in 2015.
1989 – Randy Johnson To The Mariners
The Expos knew they had something in Randy Johnson, they just didn’t know if his control would ever allow him to reach his potential. After a wild and frustrating season in 1989, the Expos traded the 6-10 flamethrower to the Mariners for established star, Mark Langston.
Langston would only pitch one season for the Expos before being traded to the Angels and continuing his fine career. Johnson would harness his control and become one the best pitchers in Major League Baseball history, being inducted into the Hall of Fame in 2015.
1990 – Jeff Bagwell To The Astros
Trading a top prospect for a rental can be a disastrous proposition for any team. While Boston native Jeff Bagwell was destroying minor league pitching, The Red Sox thought they were set at Third Base. So they traded Bagwell to Houston for Larry Anderson.
While Anderson pitched well down the stretch for the Red Sox he departed to the Padres in free agency after the season ended. Bagwell became a monster for the Astros and was elected into the Hall of Fame in 2017.
1992 – Curt Schilling To The Phillies
Curt Schilling was involved in two lopsided trades. The first saw him traded alongside Steve Finley and Pete Harnisch for Glenn Davis. The team that acquired him, the Astros, did not have enough patience with Schilling and dealt him to the Phillies for Jason Grimsley.
Schilling became a top notch pitcher for the Phillies right away and was an important piece of their 1993 World Series runner up. He was a star in Philadelphia until he was traded to the Diamondbacks in 2000.
1992 – Kenny Lofton To The Indians
While Kenny Lofton had torn up Houston’s minor league system, he only hit .203 in his Major League debut. The unimpressed Astros traded the Center Fielder to the Cleveland Indians for catching prospect Eddie Taubensee.
Lofton became the engine for the Indians very talented teams of the mid to late ’90’s. Combining excellent plate discipline, outstanding fielding and blazing speed, The Center Fielder would go on to have a 17 year, borderline Hall of Fame career.
1997 – Derek Lowe And Jason Varitek To The Red Sox
The Red Sox were brutally taken in the Babe Ruth trade in 1919. This deal, however, created the foundation of the Boston team that would end the curse. The Mariners were making a run at the pennant in 1997 and dealt prospects Jason Varitek and Derek Lowe for so-so closer, Heathcliff Slocumb.
The pair would go on the lead an up and coming Red Sox team. Varitek became the Catcher, Captain and backbone of the squad. Lowe became a top notch starter for the team who saved his best for the 2004 World Series run where the Red Sox ended the Curse of the Bambino.
Brandon Phillips, Cliff Lee And Grady Sizemore To The Indians
When the subject of lopsided trades is brought up, this deal is often referred to as the most lopsided of them all. There is a major asterisk. The Expos, who were facing a potential contraction, emptied their farm system for Pitcher Bartolo Colon in hopes to compete.
Phillps, Lee, and Sizemore all had terrific careers. Phillips later became a star with the Reds. Lee was a star for the Indians winning the Cy Young Award in 2008. Sizemore emerged as one of the very best players in baseball before a series of debilitating injuries cut his career short.
2003 – Joe Nathan To The Twins
The Giants of the early 2000’s, led by Barry Bonds and Jeff Kent, were always chasing a World Series. The team felt that they were one piece away from competing and acquired Catcher AJ Pierzynski from the Minnesota Twins.
In return, the Twins acquired prospect Francisco Liriano and Closer Joe Nathan. Liriano had some excellent years for the Twins, but injuries scuttled his career. Nathan became one of the better Relief Pitchers in recent memory, recording 260 career saves.
2003 – Adam Wainwright To The Cardinals
JD Drew was a magnificent ballplayer who was excellent when he played but often hurt. The Braves felt he would be a perfect piece for their outfield and dealt for him in 2003. Drew was spectacular in his one season for the Braves achieving an 8.6 WAR. Then, he was gone the next year.
In return, the Cardinals received among other things, pitching prospect Adam Wainwright. As of 2019, the right-hander is still pitching in St. Louis. In his 16 year Cardinal career, Wainwright has won 155 games, made 3 All-Star teams and was a major contributor to their 2006 World Series win.
2003 – Aramis Ramirez To The Cubs
At one time, The Indians got a steal in acquiring Kenny Lofton. With this trade, the team acquiring Lofton again got a great deal, but not because of the aging Center Fielder. Looking to bolster a potential playoff run, the Pirates dealt Aramis Ramirez to the Cubs in exchange for Jose Hernandez.
Ramirez, who was talented but inconsistent for the Pirates, became a star for the Cubs. He manned Third Base in Chicago for 9 seasons, making two All-Star teams and winning a Silver Slugger in 2011.
2007 – Elvis Andrus To The Rangers
The 2007 Braves were hoping to fight for one more World Series title. The team received the crown jewel of that season’s trade deadline in First Baseman Mark Teixeira. In return the Braves traded a monster package that included Jarrod Saltalamacchia, Matt Harrison and Neftali Feliz.
The main piece of the deal, though, was Elvis Andrus who remains a star for the Rangers today. Feliz, Saltalamacchia and Harrison had some nice moments for the Rangers as well. Teixeira departed the Braves at the end of the season for the Yankees.
2008 – Jose Bautista To The Blue Jays
Jose Bautista was not some major prospect dealt for a established star. He was merely a talented player who may have turned into a Quad A player who destroyed minor league pitching. After being dealt from the Pirates to the Blue Jays, he became so much more.
While with the Jays, Bautista became a major slugger who also excelled at getting on base. He not only became a great player for the Jays, but also a pillar of the Toronto community. Joey Bats made 6 All-Star teams with Toronto and won 3 Silver Sluggers.
2012 – Noah Syndergaard To The Mets
RA Dickey’s career transformation from a mediocre hard-throwing starter to an un-hittable knuckleballer that culminated with a 2012 Cy Young Award. Rather than resigning Dickey, the Mets traded him to the Blue Jays for top catching prospect, Travis d’Arnaud.
While d’Arnaud had some nice moments for the Mets, he never materialized into the front-line Catcher they hoped for. Syndergaard, the second prospect in the deal, did become a front-line Pitcher though. “Thor” helped pitch the Mets into the 2015 World Series and made the All-Star team in 2016.
2013 – Jake Arrieta To The Cubs
The Baltimore Orioles have long had issues with developing their talented minor league pitchers into successful major league starters. Jake Arrieta stands as a near perfect example of this problem. After he was beat up during his first few seasons, Arrieta was dealt to the Chicago Cubs.
It didn’t take long for him to become a star in Chicago. By 2015, the right-hander had won a Cy Young Award. By 2016, he was fronting a World Series champion. To add insult to ijury the Cubs also received Pedro Strop while dealing Scott Feldman. Strop has been a terrific reliever for the Cubs and is still an essential member of their bullpen.
2016 – Gleyber Torres To The Yankees
Flags Fly Forever. That slogan can help ease the pain of dealing a future star, but still winning a championship. It doesn’t happen for most teams, but it did for the Cubs who dealt Gleyber Torres and other prospects to the Yankees in exchange for Aroldis Chapman.
The Cubs got their World Series championship and the Yankees resigned Chapman in the offseason. They also got Torres who has become a bonafide stud. An All-Star in both 2018 and 2019, the 22 year-old will be a foundational piece for the Yankees for years to come.
2009 – Max Scherzer To The Tigers
In 2009, pitcher Max Scherzer played for the Arizona Diamondbacks, where he accumulated a 4.12 ERA and 174 strikeouts in 170.3 innings pitched. In 2009, the Diamondbacks made a three-way trade between themselves, the New York Yankees, and the Detroit Tigers. Scherzer went to the Tigers.
As of 2019, Scherzer has won three Cy Young Awards. He was so valued that in 2015, Scherzer signed a $210 million contract with the Nationals, one of the largest in all of baseball. He also became the third-fastest pitcher to achieve 2,000 career strikeouts.
1998 – Paul Konerko To The White Sox
Many sports fan don’t remember Paul Konerko playing for any team besides the Chicago White Sox. But in 1998, he was traded twice to two teams. The first time, he went to the Los Angeles Dodgers, where he made it to the big leagues. The second time, he joined the Cincinnati Reds.
After 26 games with the Reds, Konerko joined the White Sox. There, he expanded his career and won the 2005 World Series with his team. From 2006 to 2014, he was the White Sox captain. He retired afterward.
2012 – Kyle Hendricks To The Cubs
In 2012, the Chicago Cubs were rebuilding their team and trading their starting pitcher, Ryan Dempster. After a string of complications, they traded him for the Texas Rangers pitcher, Kyle Hendricks. Although Hendricks began with the Tennessee Smokies, he quickly elevated to the Cubs by 2014.
Not only did Hendricks have an impressive rookie season of 2.46 ERA, but he also become the hero of the 2016 World Series. He helped the Cubs win their first title in 108 years. In 2019, Hendricks agreed to a four-year contract extension with the Cubs, so the Rangers will never have him back.
2011 – Vernon Wells To The Angels
In 2011, Vernon Wells was ending an All-Star season for the Toronto Blue Jays. Even so, Jays traded Wells to the Los Angeles Angels, in return for Mike Napoli. Napoli was traded again a few days later.
Meanwhile, Wells “heated up” on his new team. His batting average ascended to .222 OPS, and he achieved 11 home runs in June and July, as opposed to his four the previous two months. In his Toronto game, the audience applauded him when he stepped up to bat. In 2013, Wells was traded again to the New York Yankees.
1997 – Bobby Abreu To The Phillies
In the 1997 expansion draft, the Tampa Bay Devil Rays traded their outfielder, Bobby Abreu. Although he was a hitting prospect, the Devil Rays still traded him to the Philadelphia Phillies in exchange for shortstop Kevin Stocker. The Devil Rays’s new member only garnered 2.7 WAR over three seasons.
In contrast, Abreu hit over 285 home runs with .875 OPS and 59. WAR overall. He is now a two-time All-Star with both a Silver Slugger Award and a Rawlings Gold Glove Award. In 2006, Abreu was traded to a Yankees minor league.
1910 – Joe Jackson To The Indians
Back in 1910, the Philadelphia Athletics gave up one of their most promising players. They traded their players Morrie Rath and Joe Jackson in exchange for the Cleveland Naps’s (now renamed the Cleveland Indians) Bris Lord.
While Lord made a decent 6.6 WAR in three seasons, Jackson achieved .375, .441, and .542 in his six seasons with the Indians. In 1915, he joined the Chicago White Sox, where he helped them win the American League pennant and the World Series. Jackson is now nicknamed “Shoeless” Joe Jackson.
1964 – Lou Brock To The Cardinals
In the early 1960s, Lou Brock was a promising right fielder who played for the Chicago Cubs. But after he only hit a .260 average over two seasons, they gave up on him. They traded Brock to the St. Louis Cardinals in exchange for the National League player Ernie Broglio. Afterward, Broglio only managed 3.5 WAR and .689 OPS in four seasons.
Four months after Brock joined the Cardinals, the team won the 1964 World Series. In 1974, he broke the record for the most stolen bases–118 in a single season. Throughout his 16 seasons with the Cardinals, Brock stole 888 bases with a .761 OPS and 41.6 WAR.
1997 – Pedro Martinez To The Red Sox
In 1977, Pedro Martinez was playing phenomenally for the Montreal Expos. He had an ERA of 1.90 and won the Cy Young award. Since the Expos were strapped for cash, they moved Martinez to the Boston Red Sox to avoid his salary raise, expecting a brilliant prospect in return.
Martinez led the Boston Red Sox to their first World Series win in 86 years. He won the Most Valuable Player Award and ended up in the Baseball Hall of Fame in 2015. Meanwhile, the Expos received their “prospect” Carl Pavano, who only posted a 4.83 ERA in six seasons.
1997 – Mark McGwire To The Cardinals
In 1997, the St. Louis Cardinals weren’t contending after a losing season. They wanted to add more power to their lineup, so they traded three players–T.J. Matthews, Blake Stein, and Eric Ludwick–to the Oakland Athletics. In return, they got Mark McGwire.
In his four-year career with the Cardinals, McGwire landed 220 home runs. He averaged one home run per every 10.61 bats, beating Babe Ruth’s record of one per 11.76. From 1995 to 2001, he achieved six consecutive All-Star appearances. In 2010, McGwuire coached for his St. Louis team.
1972 – Steve Carlton To The Phillies
Steve Carlton played for the St. Louis Cardinals in the late 1960s, including their 1967 World Series win. In 1971, Carlton was struggling with a salary dispute. The Cardinals traded Carlton for the Phillies’ pitcher, Rick Wise. At the time, it made sense, but it’s now considered one of the most lopsided trades in history.
In his Phillies uniform, Carlton won four Cy Young Awards and ended up in the Baseball Hall of Fame. His pitching was so vicious that slugger Willie Stargell compared it to “trying to drink coffee with a fork.” Wise, however, didn’t stay with the Cardinals.
2003 – Derrek Lee To The Cubs
In 2003, first baseman Derrek Lee played for the Florida Marlins, where he won his first Gold Glove and the team’s World Series award. Even so, the Marlins traded Lee for the Chicago Cubs’s first baseman Hee-seop Choi.
While Choi had a brief career with the Marlins, Lee remained with the Cubs for seven years and hit 179 home runs. He helped lead the team to postseason in both 2007 and 2008. In his overall career, he earned 22.5 WAR, three Golden Glove Awards, and two All-Star selections.
1984 – Willie Hernandez To The Tigers
In 1984, Willie Hernandez was an unremarkable relief pitcher for the Philadelphia Phillies. The team traded him to the Detroit Tigers in exchange for Glenn Wilson and John Wockenfuss. In the Tigers uniform, Hernandez flourished.
Hernandez helped the Tigers ascend to the 1984 world series. He won both Most Valuable Player and the American League Cy Young award that same year. Overall, he pitched 140.3 innings with 32 saves and 1.92 ERA. Meanwhile, the Phillies only managed 81-81 with 3.63 ERA from their players.
2014 – Josh Donaldson To The Blue Jays
In the early 2010s, Josh Donaldson played well for the Oakland Athletics. He won his first Fielding Bible Award and helped the team enter postseason in 2012. But when his batting average went down, the Athletics traded him to the Toronto Blue Jays for Kendall Graveman, Frank Barreto, and Sean Nolin.
In just three seasons, Donaldson accumulated a 20.9 WAR with the Blue Jays. He won the MLB Player of the Year Award, and fans would chant “M-V-P!” when he stepped up to bat. Of the three players that the Athletics received, only Graveman remained to make 4.11 ERA in three seasons.
2017 – Giancarlo Stanton To The Yankees
One of the most recent player trades has been subject to a lot of speculation. For seven years, Giancarlo Stanton played for the Miami Marlins. He played well, ending on an MVP season. To save money on him, the Marlins traded him to the New York Yankees for 17-year-old Starlin Castro.
During his debut with the Yankees, Stanton hit two home runs. By the end of 2018, he had clubbed 38 home runs, 34 doubles, a .266 batting average, and 100 RBI. He also hit the fastest exit velocity of all major leagues–a stunning 121.7 miles per hour.
2003 – Alex Rodriguez To The Yankees
Despite the Texas Rangers’ less-than-stellar performance in the early 2000s, Alex Rodriguez stood out from the crowd. He led the American League in home runs, won his second Golden Glove Award, and carried an MPV. The Rangers cashed in on Rodriguez’s success by trading him to the Yankees for second baseman Alfonso Soriano.
Soriano only played two seasons for Texas before moving on to the Washington Nationals. In contrast, Rodriguez won the World Series in a Yankees uniform. He slammed 351 home runs and became a 14-time All-Star.
1987 – Dennis Eckersley To The A’s
Dennis Eckersley used to be a pitcher for the Chicago Cubs from 1984 until 1986. He threw two shut-outs but was traded when his performance began to tank, as his personal life off the field brought him down. The Cubs gave up on Eckersley too early though, when they traded him for three minor-league players in 1987.
The Oakland Athletics transitioned Eckersley to become a closer. The change suited him well, as Eckersley became the greatest reliever in baseball history. Wearing number 43, he saved 387 games over 12 seasons. He was also awarded the Cy Young Award and MVP in 1992.
1972 – Sparky Lyle To The Yankees
The Boston Red Sox selected pitcher Sparky Lyle as a first-year draft pick in 1964, playing in the farm system. Once they called him up and made him a relief pitcher, Lyle saved 64 games over four years. In 1972, the Red Sox made the mistake of trading him to the Yankees.
Pitching for the Yankees, Lyle established himself as one of the greatest relief pitchers of the ’70s. He broke Hoyt Wilhelm’s American League record of 154 career saves and claimed the Cy Young Award in 1977. The player they traded him for, Danny Carter, ended his career in 1976.
1960 – Rocky Colavito To The Tigers
In 1959, outfielder Rocky Colavito hit four consecutive home runs in one game playing for the Cleveland Indians. The team decided to trade him for Harvey Kuenn the following year, and “The Colavito Curse” began. As a Tiger, Colavito smashed 159 home runs in four seasons.
He was an All-Star for six seasons hit over 40 home runs for three seasons. On the other hand, the Indians sunk to the bottom half of the A.L. East and stayed there for a painful 30 seasons.
1971 – George Foster To The Reds
Left fielder George Foster was one of the best right-handed sluggers of his time, playing for the San Francisco Giants the same time as Willie Mays. Just as his third season with the Giants was starting, the team traded him to the Cincinnati Reds for shortstop Frank Duffy and pitcher Vern Geishert.
As soon as he got to Cincinnati, their center fielder tore his Achilles and Foster joined the starting line-up. It took him some time for Foster to find his rhythm, but in 1976 he was hitting .343 and ended the season with 29 home runs and led the major league in RBIs at 121.
2017 – Kirby Yates To The Padres
Before being traded to the San Diego Padres, right-handed pitcher Kirby Yates played for the Tampa Bay Rays, the New York Yankees, and the Los Angeles Angels. He didn’t secure a spot in the Angels bullpen during spring training, but eventually made his way up as a reliever. On April 26, 2017, Yates was claimed off waivers by the San Diego Padres.
Once he landed in San Diego, Yates’ talent shined. In 2018, Yates was 12 for 13 in saves and threw 90 strike-outs in 63 innings. He played at the 2018 MLB Japan All-Star Series and the 2019 All-Star Game.