Arizona Diamondbacks — Max Scherzer
Trade Details: Max Scherzer and Daniel Schlereth to Detroit for Edwin Jackson and Ian Kennedy in three-team deal
The Diamondbacks have made a handful of head-scratching trades since entering the league in 1998. Following the 2003 season — just two years removed from winning the World Series — Arizona shipped Curt Schilling to Boston. In his first year with the Red Sox, Schilling went 21-6, finished second for the Cy Young, and led Boston to a World Series triumph.
Six years after trading Schilling, Arizona gave up on Max Scherzer and shipped the flamethrower to Detroit. While Ian Kennedy went on to go 21-4 in 2011, he never approached Scherzer’s level. Mad Max won his first Cy Young in ’13, won back-to-back CY’s in ’16 and ’17, and is regarded as one of the two-best pitchers of his generation (alongside Clayton Kershaw).
Atlanta Braves — Mark Teixeira
Trade Details: Mark Teixeira to LA Angels for Casey Kotchman and Stephen Marek
Teixeira gets the nod here because he was involved in two bad trades. First, Atlanta acquired Teixeira from Texas for Elvis Andrus, Neftali Feliz, Jarrod Saltalamacchia and Matt Harrison. Andrus went on to become a two-time All-Star, Feliz saved 72 games in 2010-11, Harrison was an All-Star in ’12, and all three players helped lead Texas to back-to-back American League pennants.
Teixeira played 157 games for the Braves and was incredibly good. The slugger hit 37 HR, drove in 134 runs, and slashed .295/.395/.548. However, Atlanta opted to trade Teixeira just one year after acquiring him. The following season, Teixeira (with the Yankees) finished second for the AL MVP.
Baltimore Orioles — Curt Schilling
Trade Details: Curt Schilling, Pete Harnisch and Steve Finley to Houston for Glenn Davis
Curt Schilling played for five teams during his 20-year career…and all five teams traded him. Drafted by the Red Sox in 1986, Schilling was shipped to Baltimore in ’88 before reaching the Majors. Over the course of three seasons with the Orioles, Schilling started a mere five games, appeared in 44 total games and posted a 4.54 ERA. Baltimore opted to trade the young pitcher to Houston for Glenn Davis. Over the course of three years, Davis hit .247 with 24 HR.
Schilling would go on to win 215 games, became a six-time All-Star and won three World Series after leaving town. Making the trade even worse, Harnisch and Finley both had very nice careers. Harnisch became an All-Star the next season and won 95 more games before retiring. Finley won five Gold Gloves, hit 299 HR, drove in over 1,100 runs, and made two All-Star games following the trade.
Boston Red Sox — Babe Ruth
Trade Details: Babe Ruth to the Yankees for $100,000
The most infamous trade of all-time involved Boston sending Babe Ruth to the Yankees for some much-needed cash. Ruth was arguably the league’s best player at the time, and he soon became a legend in New York. After setting the single-season home run record (29) in his final season with the Red Sox, Ruth smashed 54 and 59 homers in his first two seasons with the Yankees. Overall, Ruth slugged 659 HR in 15 seasons with the Yanks, and became one of the greatest players of all-time. As for the Red Sox, the franchise would have to wait 86 years before winning another World Series title (1918-2004).
Chicago Cubs — Lou Brock
Trade Details: Lou Brock, Jack Spring and Paul Toth to St. Louis for Ernie Broglio, Bobby Shantz and Doug Clemens
The rivalry between the Chicago Cubs and St. Louis Cardinals is not only one of baseball’s best rivalries, but it is one of the best in all of sports. There have been many players who have played for both teams, but Lou Brock is the best player to don both a Chicago ‘C’ and a cardinal during his career. Brock spent the first 3.5 seasons of his career in Chicago. While with the Cubs, Brock slashed .257/.306/.383 and hit 20 HR. In the immediate aftermath of the trade that sent him to St. Louis, Brock became a superstar. Brock hit .348 with 12 HR in his first 103 games as a Cardinal. Over the next 15 years, Brock earned six All-Star nods, won two World Series, and developed into a Hall of Fame player. At one time, Brock admitted that the Cubs “stunted his growth” (as a player).
Chicago White Sox — Fernando Tatis Jr.
Trade Details: Fernando Tatis Jr. to San Diego for James Shields and cash
You know a trade is terrible if you are able to deem it a failure within three years of its completion. In June 2016, less than a year after signing Fernando Tatis Jr., the White Sox shipped Tatis Jr. to San Diego for James Shields. At the time, a 34-year-old Shields was 2-7 with a 4.28 ERA. The veteran pitcher went 4-12 in ’16 after joining the Sox — and finished his three-year stint in the Windy City with a 16-35 record and a 5.31 ERA. As for Tatis, the rising star debuted in ’19 and hit .317 with 22 HR in 84 games. One of the game’s best players, Tatis finished fourth for the NL MVP in ’20 and third in ’21 (thanks to a 42 HR season). Ahead of the ’21 season, the Padres signed Tatis to a 14-year/$340 million deal. White Sox fans are going to hate watching Tatis for the next decade.
Cincinnati Reds — Frank Robinson
Trade Details: Frank Robinson to Baltimore for Milt Pappas, Jack Baldschun and Dick Simpson
To begin his Hall of Fame career, Frank Robinson spent 10 years playing at an MVP-level for the Cincinnati Reds. From 1956-1965, Robinson slashed .303/.389/.554 and launched 324 homers. During that time, Robinson won one MVP (’61) and finished in the top-10 of voting five times. However, Cincinnati owner Bill DeWitt believed Robinson was “an old 30,” and opted to trade the legend to Baltimore.
Robinson immediately proved DeWitt wrong — putting together a career-year for the Orioles in his debut season. En route to winning his second MVP, Robinson led baseball with 122 runs, 49 HR, 122 RBI, a .637 SLG, and a 1.047 OPS — and led the American League with a .316 BA and .410 OBP. Robinson led the Orioles to two World Series triumphs…including a 4-1 series win over the Reds in 1970.
Cleveland Guardians — Roger Maris
Trade Details: Roger Maris, Dick Tomanek and Preston Ward to Kansas City for Woodie Held and Vic Power
Cleveland hasn’t won a World Series in 75 years — the longest stretch in baseball. Now known as the Guardians, Cleveland has a history of trading away its top players. Many decades before Cleveland sent Francisco Lindor, a star shortstop in his prime, to the Mets, the franchise gave up on a man named Roger Maris. Maris began his career with Cleveland, but he was traded after playing just 167 games for the Indians. One year after shipping Maris to the A’s, the future Hall of Famer made his first All-Star team. Within three years, Maris had won two back-to-back MVPs and hit a then-record 61 home runs (1961). Cleveland should have been a bit more patient with Maris.
Colorado Rockies — Nolan Arenado
Trade Details: Nolan Arenado to St. Louis for Austin Gomber and four Minor Leaguers
In 2019, Nolan Arenado signed an eight-year/$260 million contract extension with the Colorado Rockies. Prior to signing the extension, Arenado had put together three-straight top-5 MVP seasons. From 2013-2019, Arenado averaged 32 HR and 105 RBI per season. Additionally, the superstar third baseman was arguably the best defensive player in baseball. Now a Cardinal, Arenado finished third for the NL MVP in 2022.
Arenado was on track to become the greatest player in Rockies history, and Colorado had to send St. Louis $50 million to complete the deal. Yes, the Rockies actually traded a perennial MVP contender and $50 million for four Minor Leaguers and one mediocre starting pitcher (Gomber).
Detroit Tigers — John Smoltz
Trade Details: John Smoltz to Atlanta for Doyle Alexander
When looking at John Smoltz’s performance in Double-A in advance of this trade, it’s easier to understand Detroit’s thought process. In 1987, Smoltz went 4-10 with a 5.68 ERA. Doyle Alexander went 9-0 for the Tigers following the deal, and helped guide the team to the postseason. Alexander would also make the All-Star team the following season, but Smoltz would soon emerge as an even bigger star. In ’89, Smoltz threw five complete games for the Braves and was deemed an All-Star. Of course, Smoltz would go on to win a Cy Young (’96) and 213 games over 21 years. At one point, Smoltz also became the league’s top closer — racking up 144 saves in three years before transitioning back into the starting rotation.
Houston Astros — Joe Morgan
Trade Details: Joe Morgan, Jack Billingham, Cesar Geronimo, Denis Menke and Ed Armbrister to Cincinnati for Lee May, Tommy Helms and Jimmy Stewart
The Astros made two terrible trades within three years of each other. In 1968, Houston sent pitcher Mike Cuellar to Baltimore. Cuellar won the Cy Young in ’69 and averaged 21 wins over the next six seasons. Following the ’71 season, Houston sent Joe Morgan to Cincinnati. While with the Astros, Morgan was a two-time All-Star and stole at least 40 bases each of his final three seasons with the club. However, Morgan blossomed into a Hall of Famer with the Reds.
From 1972-76, Morgan slashed .303/.431/.499, won four Gold Gloves, went to five-straight All-Star Games, and claimed back-to-back NL MVPs (’75, ’76). Freed from the cavernous Astrodome, Morgan’s power stroke came through and he became baseball’s best player. Two MVPs, two World Series, one happy team, one very sad team — the results of the Joe Morgan trade.
Kansas City Royals — David Cone
Trade Details: David Cone to the Blue Jays for Chris Stynes, Tony Medrano and Dave Sinnes
This one has to sting more than most. David Cone was a native of Kansas City and was a well-known, two-sport athlete in high school. For some odd reason, the Royals decided it was a good idea to trade a talented young pitcher twice(!). Kansas City first traded Cone in 1987 — to the Mets — and shipped him off for a second time in ’95. Cone was a two-time All-Star with the Mets, and went 27-19. Upon rejoining the Royals, Cone reached his third All-Star Game and won the AL Cy Young. As such, people around the league were shocked when Kansas City opted to trade Cone once again. Cone would go on to win a total of five World Series outside of Kansas City.
Los Angeles Angels — Jim Edmonds
Trade Details: Jim Edmonds to St. Louis for Kent Bottenfield and Adam Kennedy
The Angels are more known for bringing in All-Star talent than they are trading it away, but they have shipped off a few stars over the years. This includes OF Jim Edmonds. From 1993-1999, Edmonds was a very productive player for the Angels. During that time, Edmonds hit .291, slugged 121 homers and played an excellent centerfield. Edmonds was a star defensively — winning two Gold Gloves and routinely making extraordinary plays in the outfield. However, the Angels decided they were better off trading the young star following the ’99 season.
In Edmonds’ first five seasons with the Cardinals, the star won five Gold Gloves and averaged 36 HR and 100 RBI per year. Adam Kennedy was a key contributor to the Angels’ World Series run in 2002, but Edmonds would have extended their title-contending window.
Los Angeles Dodgers — Pedro Martinez
Trade Details: Pedro Martínez to Montreal for Delino DeShields
The Dodgers traded away two future Hall of Famers — Mike Piazza and Pedro Martinez — and a future six-time All-Star (Paul Konerko) within five years of each other. The Piazza trade netted LA Gary Sheffield and Todd Zeile, while the trade for Martinez brought back Delino DeShields. Trading away Martinez was baffling. As a 21-year-old, Martinez went 10-5 with a 2.61 ERA. Additionally, Pedro’s brother, Ramon, was a starting pitcher for the Dodgers.
The Expos immediately turned Martinez into a starter, and it didn’t take long for him to become an ace. Pedro won his first Cy Young in 1997 (Year 4 in Montreal) and would go on to win two more CY’s over the next three seasons. Martinez developed into one of the greatest pitchers of all-time, and DeShields hit .241 over three seasons in Los Angeles.
Miami Marlins — Miguel Cabrera
Trade Details: Miguel Cabrera and Dontrelle Willis to Detroit for Andrew Miller, Cameron Maybin and four other players
The Florida/Miami Marlins have had numerous great players in their clubhouse over the years, but a vast majority of them have been traded at some point. In recent years, the Marlins have shipped away Giancarlo Stanton (who won the MVP the year before) and Christian Yelich — who went on to win the MVP in Milwaukee and finish second the following season. The Marlins even acquired Mike Piazza from the Dodgers back in the 1990s…only to trade him to the Mets eight days later.
In advance of the 2008 season, the Marlins moved Miguel Cabrera and Dontrelle Willis to the Tigers. Both players played a pivotal role for the ’03 World Series champs, and Cabrera was already a four-time All-Star at the age of 24. Of course, Cabrera would continue to excel away from the Marlins. With the Tigers, Cabrera won two MVPs, a Triple Crown, and four batting titles. It’s never a good idea to give away a future first-ballot Hall of Famer.
Milwaukee Brewers — Nelson Cruz
Trade Details: Nelson Cruz and Carlos Lee to Texas for Francisco Cordero, Laynce Nix and Kevin Mench
Talk about a whiff. In 2006, the Brewers sent slugger Carlos Lee to the Rangers in exchange for three players. Lee was an All-Star in both ’05 and ’06, and was in the midst of a five-year run of hitting 30+ home runs. Unfortunately for the Brewers, the prospect they included in the trade — Nelson Cruz — ended up being even better than Lee. It took him a few years to get going, but Cruz developed into one of baseball’s best power hitters. A seven-time All-Star, Cruz hit 464 home runs during his career.
Minnesota Twins — Rod Carew
Trade Details: Rod Carew to LA Angels for Ken Landreaux, Dave Engle, Brad Havens and Paul Hartzell
Imagine your favorite team trading away a player who won an MVP, seven Batting Titles, and reached 12 All-Star Games before turning 33. If you are a fan of the Minnesota Twins, you lived through this exact scenario. Unwilling to meet Rod Carew’s terms on a new contract, the Twins traded the future Hall of Famer to the Angels for four players in 1979. Carew had just won his sixth Batting Title in seven years and was only one year removed from winning the American League MVP. As an Angel, the Minnesota legend hit .314 and reached six more All-Star Games before hanging up his spikes.
New York Mets — Tom Seaver
Trade Details: Tom Seaver to Cincinnati for Pat Zachry, Steve Henderson, Doug Flynn and Dan Norman
Say hello to the New York Mets — the second franchise in as many slides to trade away an iconic player for no good reason. Entering the 1977 season, Tom Seaver had already won three Cy Youngs, the Rookie of the Year, and was an eight-time All-Star with the Mets. Through the first 10 years of his career, Seaver went 182-107 with a 2.47 ERA. As a result of a bitter relationship between the star pitcher and the Mets’ chairman, Seaver was traded to Cincinnati at the trade deadline. Seaver would go on to win 56 games for the Reds between 1977-1981 and finished in the top-5 of Cy Young voting three times. Meanwhile, the Mets would proceed to lose at least 90 games seven seasons in a row.
New York Yankees — Rickey Henderson
Trade Details: Rickey Henderson to Oakland for Luis Polonia, Eric Plunk and Greg Cadaret
Before joining the Yankees in 1985, Rickey Henderson established himself as one of the game’s best players while in Oakland. Through the first six years of his career, Henderson slashed .292/.400/.408 and stole an unfathomable 493 bases. Henderson continued to star in the Bronx — reaching the All-Star Game four years in a row and adding 301 steals to his tally. However, as the Yankees struggled to compete in ’89, New York traded the star back to Oakland. In Henderson’s first full-season back with the A’s, he won the American League MVP award. While Henderson’s star dimmed a bit in the subsequent years, it is a trade that the Yankees surely regret.
Oakland Athletics — Roger Maris
Trade Details: Roger Maris, Kent Hadley and Joe DeMaestri to the Yankees for Don Larsen, Marv Throneberry, Norm Siebern and Hank Bauer
Two teams were dumb enough to trade Roger Maris. A little more than a year after acquiring Maris from the Indians, the then-Kansas City Athletics sent the future Hall of Famer to the Yankees. The year before, in 1959, Maris was deemed an All-Star for the first time. Maris had displayed a good power stroke to start his career — 58 HR in three seasons — but the A’s couldn’t have predicted what would happen next. In his first two years in Pinstripes, Maris launched 39 and 61 dingers. Maris’ performance netted the Minnesota native back-to-back MVPs.
Philadelphia Phillies — Ryne Sandberg
Trade Details: Ryne Sandberg and Larry Bowa to the Cubs for Ivan de Jesus
This move made a ton of sense for the Cubs. Shortly after the Phillies won the 1980 World Series, the Cubs hired Dallas Green — Philadelphia’s manager — to be their new general manager. Ahead of the 1982 season, Green targeted Larry Bowa. An aging star, Bowa was a five-time All-Star with the Phillies — but he was clearly in decline. The Phillies sent Bowa and Ryne Sandberg — a good prospect who struggled in limited action in ’81 — to Chicago for Ivan de Jesus, a mediocre shortstop. While Bowa continued to decline, Sandberg blossomed into a star. Sandberg won the National League MVP in 1984, and put together a Hall of Fame career with the Cubs. In 15 years in the Windy City, Sandberg won nine Gold Gloves, seven Silver Sluggers, and reached 10 All-Star Games.
Pittsburgh Pirates — Ralph Kiner
Trade Details: Ralph Kiner and three other players to the Cubs for six players and $150,000
Ralph Kiner was a superstar from the moment he entered Major League Baseball. Making his debut as a 23-year-old in 1946, Kiner led the league with 23 home runs. In Year 2, Kiner finished sixth for the MVP after slugging 51 homers. Overall, Kiner hit 294 HR in his first seven years with the Pirates — leading the league in all seven years. However, the Pirates hired Branch Rickey after the 1950 season, and the legendary skipper didn’t gel with Kiner. Rickey was not shy about his disdain for the Pittsburgh legend, and Kiner was ultimately dealt to the Cubs in ’53. A bad back forced Kiner to retire following the ’55 season, but the Pirates still lost this deal.
San Diego Padres — Ozzie Smith
Trade Details: Ozzie Smith and Steve Mura to St. Louis for Garry Templeton and Sixto Lezcano
Ozzie Smith’s departure from San Diego was ugly. One of the greatest defensive shortstops of all-time, Smith spent the first four years of his career with the Padres. During that stint, Smith won his first Gold Glove, stole 147 bases, and reached his first All-Star Game. However, Smith and the franchise couldn’t agree on a new contract. The situation quickly spiraled out of control. Joan Kroc, wife of Padres’ owner Ray Kroc, told Smith that if he needed more money, he could work as a gardener at her mansion…Smith gladly joined the Cardinals and the rest is history. With the Cardinals, Smith won 12 Gold Gloves, the 1982 World Series, and was a 14-time All-Star.
San Francisco Giants — Gaylord Perry
Trade Details: Gaylord Perry and Frank Duffy to Cleveland for Sam McDowell
Gaylord Perry spent the first 10 years of his career with the Giants. In that decade of action, Perry won 134 games and posted an impressive 2.96 ERA. However, the Giants believed that they could improve their team following the 1971 season by shipping a 32-year-old Perry to Cleveland for Sam McDowell — a 29-year-old ace. In ’72, McDowell battled a bum shoulder and a debilitating alcohol problem — ultimately resulting in his San Francisco tenure ending with a 11-10 record.
Conversely, Perry continued to pitch at a high level for a very long time. Perry claimed the AL Cy Young in his first year with Cleveland and won a second CY in ’78 (with San Diego). Overall, Perry won 180 games after the Giants kicked him out of town.
Seattle Mariners — Randy Johnson
Trade Details: Randy Johnson to Houston for Freddy Garcia, Carlos Guillen and John Halama
Randy Johnson remains an intimidating figure more than a decade after his retirement. At 6-foot-10, Johnson is arguably the most feared pitcher of all-time. Blessed with a lethal fastball and devastating slider, ‘Big Unit’ dominated baseball for two decades. The Mariners traded for Johnson in 1989, and the lefty turned into an ace shortly after. Between 1990-97, Johnson led the league in strikeouts four times (1,845 total SO) and had four top-3 Cy Young finishes — winning the award in ’95.
The Mariners opted to trade Johnson after a sluggish start to the ’98 season, but the 34-year-old was just getting started. From 1999-2002, Johnson won four-straight CY’s with the Diamondbacks. In addition to leading Arizona to a title, Johnson fanned 1,417 batters during his remarkable stretch — and finished second for the CY at the age of 40. Johnson proved the Mariners wrong.
St. Louis Cardinals — Steve Carlton
Trade Details: Steve Carlton to Philadelphia for Rick Wise
Just like the Mariners traded Randy Johnson away before his peak, the Cardinals gave up on Steve Carlton before he became a premier pitcher. Carlton spent the first seven years of his career with the Cardinals — going 77-62 with a 3.10 ERA. Despite reaching three All-Star Games, the Cards traded Carlton to Philadelphia for Rick Wise. Wise would pitch two seasons for the Cardinals and earned one All-Star nod while donning the STL hat. However, Carlton went on to win four Cy Youngs and 241 games with the Phillies. Do you think the Cardinals could have used Carlton between 1972-1985?
Tampa Bay Rays — David Price
Trade Details: David Price to Detroit for Willy Adames, Drew Smyly and Nick Franklin
The Rays joined Major League Baseball in 1998, so the franchise doesn’t have too many players who have blossomed into stars after being shipped out of town. However, Tampa has moved its two biggest stars in franchise history — David Price and Evan Longoria. When it comes to Price, the lefty out of Vanderbilt was an ace in just his second full season. In 2010, Price went 19-6 with a 2.72 ERA — resulting in an All-Star nod and a second-place finish for the AL Cy Young.
Two years later, Price won 20 games en route to his first Cy Young. But two years later, the Rays sent Price on his way. In his first full season away from Tampa, Price finished second for the CY while pitching for the Tigers and Blue Jays. In 2018, Price played a big role for the World Series champion Red Sox — a result that had to sting Tampa fans to their core.
Texas Rangers — Alex Rodriguez
Trade Details: Alex Rodriguez and cash to the Yankees for Alfonso Soriano and Joaquin Arias
On January 26, 2001, Alex Rodriguez signed a 10-year/$252 million contract with the Texas Rangers. By the time A-Rod joined the Rangers, he was a four-time All-Star and a perennial MVP contender. In the first three years of his deal with Texas, A-Rod hit .305, averaged 52 HR and 132 RBI, and won an MVP. Despite seven years remaining on the deal, the Rangers traded their superstar shortstop to the Yankees as the weight of his contract became too much to handle. Alfonso Soriano was a good player, but he spent just two years in Texas before the team flipped him to Washington. Meanwhile, A-Rod spent the last 12 years of his career in New York — winning two MVPs and a World Series.
Toronto Blue Jays — Roy Halladay
Trade Details: Roy Halladay to Philadelphia for Kyle Drabek, Travis d’Arnaud and Michael Taylor
One of the best pitchers from the 2000s, Roy Halladay utilized a four-pitch repertoire for much of his career — relying heavily on a devastating two-seam fastball. Halladay captured two Cy Young Awards (2003, 2010), the first of which came while Halladay pitched for the Blue Jays. Halladay debuted with Toronto in 1998, and remained with the franchise through the 2009 season. As a Blue Jay, Halladay went 148-76 and had five top-5 finishes for the Cy Young.
Ahead of the 2010 season, Toronto sent its ace to Philadelphia. Halladay promptly threw two no-hitter’s during the 2010 season. This included a perfect game on May 29, and another no-hitter in the postseason against the Cincinnati Reds. He won his second Cy Young in the process. Halladay was incredible once again in ’11, finishing runner-up for the CY while compiling a 19-6 record with a 2.35 ERA.
Washington Nationals (Montreal Expos) — Pedro Martinez
Trade Details: Pedro Martinez to Boston for Carl Pavano and Tony Armas
Before the Washington Nationals became a team in 2005, the franchise was known as the Montreal Expos. As we discussed earlier, the Expos pulled off a grand heist in 1994 by executing a trade with the Dodgers for Pedro Martinez. As an Expo, Martinez won 55 games in four seasons and developed into a true ace. In his final season with the club, Martinez posted a 1.90 ERA, threw 13 complete games, and won his first Cy Young. Unfortunately, Martinez had one year left on his deal and was likely to leave town after his final season.
So, the Expos sent Martinez to Boston for top prospect Carl Pavano and Tony Armas. Armas went 48-60 with the franchise, Pavano went 24-35. And Pedro? In his first three years with the Red Sox, Martinez won two Cy Young Awards (finished second for a third), and won 60 games with a 2.25 ERA. From his final year with the Expos to his final year with the Red Sox, Martinez went 134-45.