MLB Power Rankings: The Worst Trades in Each Team's History
The Hot Stove season has just about cooled off.
There were plenty of high-profile moves: Zack Greinke to Milwaukee, Cliff Lee to Philadelphia, Jayson Werth to Washington.
Only time will tell if those moves were great, lukewarm or horrible.
That has us thinking about the worst trades in the history of each team.
You’ll cringe when remembering these deals, but at least you can take comfort in the fact that the other 29 MLB clubs have made just as depressing moves.
Tampa Bay Rays: Trading Randy Winn to Seattle
1 of 30
When: 2002
In Exchange For: IF Antonio Perez
Obviously, the Rays have a short history, so there aren’t that many trade blunders to choose from.
Randy Winn isn’t exactly Cooperstown-bound, either.
But he turned out to become a pretty good player.
After his All-Star season in 2002 (14 HR, 75 RBI, .298 average) the Rays dealt him to the Mariners in the offseason.
In return they received Antonio Perez, who lasted just one season in Tampa.
Since then, Winn has had several productive seasons, including three straight seasons in which he topped .300.
New York Yankees: Trading Willie McGee to St. Louis
2 of 30
When: 1981
In Exchange For: P Bob Sykes
Ahh, I bet you thought we’d go with the Seinfeld reference here: Frank Costanza’s tirade at George Steinbrenner for trading Jay Buhner for Ken Phelps.
Sure, Buhner was a good player, but McGee had a better career.
He won a batting title and NL MVP in 1985, was a four-time All Star and a Gold Glove outfielder.
And at least Phelps actually played parts of two seasons with the Yankees: Bob Sykes, who they got in return for McGee, never threw a single pitch for the Yanks' big league club.
Boston Red Sox: Selling Babe Ruth to the New York Yankees
3 of 30
When: 1919
In Exchange For: $100,000
Do we even need to explain?
Boston’s made some blunders over the years, including shipping Jeff Bagwell to the Astros for Larry Anderson.
Still, selling Ruth to the Yankees—who promptly became the greatest franchise in American sports history—was light-years worse.
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Baltimore Orioles: Trading Curt Schilling and Steve Finley to Houston
4 of 30
When: 1991
In Exchange For: 1B Glenn Davis
You really can’t blame the Orioles for making this move at the time. Schilling never won a start in three seasons with Baltimore and Finley didn’t do very much in his two years with the club.
Furthermore, Glenn Davis was a pretty big star for the Astros in the mid-1980s, and he was only 29 at the time of the deal.
But after three terribly disappointing seasons with the Orioles, Davis was out of the game.
Finley became a very good bat and an even better glove during the next decade-and-a-half.
Schilling, well, he only became one of the modern game’s greatest postseason pitchers.
Toronto Blue Jays: Trading David Cone
5 of 30
When: 1995
In Exchange For: P Marty Janzen
Why did no one seem to want David Cone?
After 76 wins in six seasons in New York, the Mets traded him away for little in return, something the Royals actually did twice.
But the Blue Jays saw enough of Cone after only 17 starts.
Midway through his first season north of the border, the Jays sent Cone to the Yankees in exchange for almost nothing.
It was bad enough that they gave him to a division rival, but that they just missed out on a pretty formidable duo of Cone and Roger Clemens.
In 1998, Cone was a 20-game winner and the best pitcher on the historic Yankees World Championship team.
At least they got David Wells and Homer Bush when they shipped Clemens to New York, and Kyle Drabek in exchange for Roy Halladay. Marty Janzen lasted only two years in the big leagues.
Cleveland Indians: Trading Rocky Colavito to Detroit
6 of 30
When: 1963
In Exchange For: IF Harvey Kuenn
For the course of a century, the Red Sox had the Curse of the Bambino. They’ve finally “reversed” it.
The Indians are still mired in the so-called “Curse of Rocky Colavito.”
After missing out on the AL pennant by just a few games, the Indians traded extremely popular outfielder Rocky Colavito—a 40-plus homer hitter each of the previous two seasons—to the Tigers for Harvey Kuenn.
Kuenn, the AL’s batting champion, lasted just one season in Cleveland and was sent to San Francisco.
Colavito flourished in Detroit, hitting 139 home runs and driving in 430 runs over the next four seasons.
The Indians would eventually get him back in 1965, but had they not dealt the righty away in his prime, perhaps 41 years wouldn’t have gone by (1954-95) without a postseason appearance.
Chicago White Sox: Trading Sammy Sosa to the Chicago Cubs
7 of 30
When: 1992
In Exchange For: OF George Bell
Here’s another case of good intentions gone horribly wrong.
(And for the time being, let’s put all the steroid talk on hold when reading this entry).
George Bell was a fine slugger for the Blue Jays. After his 47-homer, 134-RBI season in 1987, he never again was an MVP candidate. But he was still good for 20-or-so home runs and roughly 100 RBI.
So when the White Sox, who were a serious contender each year in the AL West, were able to acquire Bell for a young hitter who hit .230 and struck out a ton, it was almost a no-brainer.
But Bell only played two seasons in Chicago before retiring. Sosa turned into a prolific home-run hitter and MVP.
Still, what makes this the worst trade in franchise history is the fact that they gave him to their cross-town rival and sent tens of thousands of new fans flocking to the North Side each summer.
Detroit Tigers: Trading John Smoltz To Atlanta
8 of 30
When: 1987
In Exchange For: P Doyle Alexander
This one hurt for a variety of reasons.
For one, after the move, Smoltz became a dominant starter, then a dominant closer, then a dominant starter again, while the Braves were a postseason participant every year.
On the other end of the deal, Alexander, who had a great reputation but was 37 years old, flamed out after a phenomenal 9-0 start in Detroit. Following a league-high 18 losses, Alexander retired following his third year in Detroit.
But the worst part of the deal? Smoltz was born and raised in Detroit!
Kansas City Royals: Trading Johnny Damon to Oakland
9 of 30
When: 2001
In Exchange For: CL Roberto Hernandez
The Royals certainly didn’t get fair value in return when they dealt Carlos Beltran to the A’s, but they at least got a regular starter (catcher John Buck) for the next six years in exchange for a player they had no hopes of re-signing.
All they got in exchange for a 26-year-old Johnny Damon was Roberto Hernandez, a closer whose best years were behind him.
Damon only spent one season in Oakland but would go on to be the lynchpin of the Red Sox World Series team in 2004, as well as a key member of the Yankees team that won the World Series five years later.
Minnesota Twins: Trading Scott Erickson to Baltimore
10 of 30
When: 1995
In Exchange For: P Scott Klingenbeck and OF Kimera Bartee
The Twins have fleeced several other clubs: the Giants and Yankees come to mind.
And they probably wanted to unload high-salaried Scott Erickson, who had been struggling a great deal since his outstanding season in 1991.
But the Twins only got seven starts out of Klingenbeck and nothing out of Bartee.
Since Erickson went on to average 15 wins over the next four years and was a solid postseason starter, it was a major miscalculation.
Oakland A’s: Trading Mark McGwire to St. Louis
11 of 30
When: 1997
In Exchange For: P Eric Ludwick, P Blake Stein, P T.J. Mathews
McGwire may have been 33 at the time, but—after two injury-riddled seasons—he had returned to his post as one of the American League’s best power hitters.
And McGwire really wanted to be reunited with Tony La Russa.
So you can’t really blame the A’s for sending McGwire to St. Louis.
But if you’re going to move one of the greatest right-handed power hitters ever, you’d better get more in return than two starters who win a combined six games, and a mediocre middle reliever.
Texas Rangers: Trading Travis Hafner to Cleveland
12 of 30
When: 2003
In Exchange For: C Einar Diaz and P Ryan Drese
His career may have been derailed by injuries, but for a four-year stretch, Hafner was one of the most formidable left-handed bats in the American League.
From 2004-07, he hit 127 home runs, knocked in over 100 runs per season and kept his average around .300.
And all the Indians had to give up to get him was a light-hitting catcher and a starter who the Rangers later waived.
It begs the question: How would the AL Champion Rangers fared in last year’s World Series with Pronk in the lineup?
Seattle Mariners: Trading Derek Lowe and Jason Varitek To Boston
13 of 30
When: 1997
In Exchange For: RP Heathcliff Slocumb
Another in the long-line of regrettable deadline deals.
In their defense, the Mariners were a World Series contender when they made this move: understandably all they needed was a top-notch closer. But they didn’t get one.
Seattle sent a rookie (Lowe) and a minor leaguer (Varitek) to the Red Sox for Slocumb, a closer who was struggling but had posted 80 saves during the previous three years.
Varitek and Lowe would ultimately become cornerstones of the Red Sox revival of the late 1990s and early 2000s.
Slocumb struggled during his first half-season in Seattle, couldn’t win the closer’s job a year later, and left via free agency after 1998.
Anaheim Angels: Trading Dante Bichette to Milwaukee
14 of 30
When: 1991
In Exchange For: RF Dave Parker
A classic case of unproven prospect for established veteran gone wrong.
Bichette had done very little in his first three seasons with the Angels: 18 home runs, .244 average, in 178 games.
So shipping him to Milwaukee and getting a fairly prominent name like former NL MVP Dave Parker made sense. And Parker had been an All-Star the previous season.
But he didn’t even last a full year in California. The Halos cut him late in the season and he was out of baseball a month later.
Bichette only had two lackluster years in Milwaukee and his impressive offensive totals in Colorado were certainly aided by the thin Denver air.
Still, it was a terribly lopsided deal.
New York Mets: Trading Nolan Ryan to California
15 of 30
When: 1971
In Exchange For: IF Jim Fregosi
Back in the early 1970s, Nolan Ryan wasn’t the Nolan Ryan we know today. So it’s understandable why he wasn’t “untouchable” when the pennant contending Mets were looking to add a middle infielder with some pop.
But Ryan had been improving each year he was in the Big Apple and by 1971, he had already proven his worth as a clutch pitcher during the 1969 postseason.
And almost overnight, Ryan became a lights-out starter in his first season with the Angels, winning 19 games and leading his league in strikeouts, something he would do 10 more times by the time his Hall of Fame career was over.
Fregosi, who had been a six-time All Star in California but saw his average drop substantially in 1971, lost his job to Wayne Garrett, and survived just a year and a half in New York before the Rangers bought out his contract.
Atlanta Braves: Trading Andre Thornton To the Chicago Cubs
16 of 30
When: 1973
In Exchange For: 1B Joe Pepitone
Even after leaving New York for Houston and then Chicago, Joe Pepitone was still a fairly big-name player in the early 1970s. He had been a productive power hitter for the Yankees during the last few seasons of that dynasty.
So when the Braves were able to acquire him for a minor-leaguer, it was almost a no-brainer.
But Pepitone only played three games for Atlanta before leaving the majors to go play in Japan.
Andre Thornton, the minor leaguer the Braves sent to the Cubs in exchange for Pepitone, had a few pretty decent seasons in the Windy City before becoming an All-Star and great run producer in Cleveland during the late 1970s and early 1980s.
Florida Marlins: Trading Derrek Lee To The Chicago Cubs
17 of 30
When: 2003
In Exchange For: 1B Hee-Seop Choi
As is the Marlins' trademark, salary was a main reason why the Marlins unloaded Lee, arguably the game’s most complete first baseman, to the Cubs.
But money alone cannot excuse dealing a Triple Crown threat and Gold Glove defender in exchange for a player who was out of Major League Baseball by the age of 26.
After a marginal half-season in Florida, Hee-Seop Choi was a throw-in on the Brad Penny deal to the Dodgers and was released the following season.
Montreal Expos/Washington Nationals: Trading Randy Johnson to Seattle
18 of 30
When: 1989
In Exchange For: P Mark Langston, P Mike Campbell
Another prime example of 20/20 being hindsight.
At the time, no one knew that Randy Johnson would become the most dominant left-hander since Sandy Koufax…..although maybe his 6’10” frame and blazing fastball should have been an indication.
And the Expos did get a quality player in return, former 19-game winner and three-time AL strikeout champion Mark Langston.
But—as Johnson would later do with the Astros—Langston only spent part of one season in Montreal before leaving as a free agent (Campbell never pitched an inning for the Expos).
Even to this day, trading away the five-time Cy Young winner for almost nothing has to sting any Expos fans that might still exist.
Philadelphia Phillies: Trading Ryne Sandberg To The Chicago Cubs
19 of 30
When: 1982
In Exchange For: SS Ivan De Jesus
Arguably the worst type of “bad trade” comes when a team sends away a future star as just a throw-in.
Somehow that seems to make the front office’s incompetence grow exponentially.
That was the case of the Phillies in 1982.
Philadelphia and the Cubs seemed content to just swap starting shortstops: perennial All-Star but aging shortstop Larry Bowa would go to the Cubs, who would get a younger, and reliable player, Ivan De Jesus, at the same position.
To sweeten the deal, the Cubs also received a 22-year-old second baseman who had just one hit during a late season call-up the previous fall.
That player turned out to be Ryne Sandberg, nine-time Gold Glove winner, 10-time All Star and, eventually a Hall of Famer.
De Jesus spent just three seasons in Philadelphia, and after 1984—the year in which Sandberg won the NL MVP—was traded to St. Louis.
Pittsburgh Pirates: Trading Doc Ellis and Willie Randolph to the Yankees
20 of 30
When: 1975
In Exchange For: P Doc Medich
This move did nothing to cripple the Pirates: they averaged 92 wins a season the following three years then won the World Series in 1979.
But it was still a terrible trade.
Along with starter Dock Ellis, who would win 17 games the next season, the Pirates sent rookie shortstop Willie Randolph to the Yankees.
In return, they received Doc Medich, who went 8-11 as starter and was sent packing after just one season.
Ellis (and Ken Brett) didn’t last long in New York, either, but Randolph would become a fixture at second base for the Yankees during the next decade.
Chicago Cubs: Trading Lou Brock to St. Louis
21 of 30
When: 1964
In Exchange For: P Ernie Broglio, OF Doug Clemens, P Bobby Shantz
This might be the most infamous of all the bad player-for-player trades ever.
As you all know, Brock would go on to become a member of the 3,000-hit club, rewrite virtually every stolen-base record, and slide right into Cooperstown.
Broglio won just seven of his 33 starts in Chicago, Shantz was released the following August, and Clemens was sent to Philadelphia after just one full season.
Nevertheless, it’s clearly the worst trade in team history for one reason: not only did they GIVE UP a Hall of Famer, they handed one over to their arch-rivals, who promptly won two World Series over the next four years.
Cincinnati Reds: Trading Frank Robinson To Baltimore
22 of 30
When: 1965
In Exchange For: P Milt Pappas, OF Dick Simpson, P Jack Baldschun
Annie mentioning this deal in the opening of "Bull Durham" isn’t the only reason this bad trade lands a spot here.
For one, the Reds got very little production in return: Baldschun was a mediocre reliever for two seasons before Cincinnati released him. Simpson was primarily a pinch-hitter before being dealt to St. Louis in 1968. And Pappas was also shipped out of town after just a few seasons, following a 30-29 record.
The player they gave up in that brilliant move, Frank Robinson, won the AL Triple Crown the following season, helped the team win two World Series, and four more pennants over the next five years, and was a first-ballot Hall of Famer.
But because the Reds publicly defended the trade at the time by saying that the 30-year-old Robinson was (essentially) “washed up,” it’s one of the worst decisions in major league history.
St. Louis Cardinals: Trading Steve Carlton to Philadelphia
23 of 30
When: 1972
In Exchange For: P Rick Wise
Rick Wise was a very good pitcher. He won 15 or more games five times, was a two-time All Star, and started and won Game Three of the 1975 ALCS, sending the Red Sox to the World Series.
Still, he was no Steve Carlton. Not even close.
Right after joining the Phillies, he enjoyed arguably the finest season a starting pitcher ever had. On a team that went 59-97, Carlton led the majors with 27 wins and a 1.97 ERA. That year, he won his first of a record four Cy Young Awards.
By the time he left Philadelphia—13 years after Wise has left St. Louis—Carlton had posted 241 wins, 39 shutouts and 3,031 strikeouts.
Milwaukee Brewers: Trading Gary Sheffield To San Diego
24 of 30
When: 1992
In Exchange For: P Ricky Bones, OF Matt Miske, IF Jose Valentin
Valentin, Bones, and Miske each performed well for the Brewers in the few seasons immediately following this move. So it wasn’t a total catastrophe.
But considering what Sheffield did for the Padres, Milwaukee probably could have done a lot better.
Sheffield won the NL batting title his first season in San Diego, hit 33 home runs, and drove in 100 runs.
The following year, the Padres dealt Sheffield to Florida, where he hit third on a World Series-winning club.
Nevertheless, the Padres were pretty happy with the deal: it landed them Trevor Hoffman.
Houston Astros: Trading Joe Morgan, Cesar Geronimo, Jack Billingham to Reds
25 of 30
When: 1971
In Exchange For: IF Lee May, IF Tommy Helms, IF Jimmy Stewart
Maybe—although it’s not a certainty—it would have been a fair deal for the Astros to trade Cesar Geronimo and Jack Billingham to the Reds and received May, Helms and Stewart.
May was one of the National League’s most fearsome right-handed power hitters; Billingham won 65 games from 1972-75 and Geronimo soon became a Gold Glove outfielder for the Reds. That sounds like a fairly reasonable trade.
But when you consider that the Astros also gave up Joe Morgan—a winner of consecutive NL MVPs, a five-time Gold Glover, and a future Hall of Famer—it’s obvious that the Astros were completely hoodwinked.
Consider it this way: three vital pieces of the Big Red Machine went to the Reds in exchange for a package of players that were each gone within four years.
New York/San Francisco Giants: Trading Francisco Liriano, Joe Nathan to Twins
26 of 30
When: 2003
In Exchange For: C A.J. Pierzynski
Pierzynksi is a fine player and helped the White Sox win the World Series. But why trade anyone—even if they are prospects—for a player who you are just going to release after one year?
The Giants gave Minnesota up two exceptional pitchers and soon-to-be All Stars, closer Joe Nathan and starter Francisco Liriano, for Pierzynski, whom spent one decent season by the Bay before the team cut him in the offseason.
It’s one thing to trade away budding superstars for a player who just doesn’t produce. It’s another to trade away budding superstars for a player who you have to unload at the end of the season because he is a “clubhouse cancer.”
It’s a good thing the Giants finally won the World Series or the Pierzynski deal might have taken on curse-like status.
Brooklyn/Los Angeles Dodgers: Trading Pedro Martinez to Montreal
27 of 30
When: 1993
In Exchange For: 2B Delino DeShields
In the early 1990s, DeShields had a fine career in Montreal. He almost won the Rookie of the Year award, was a prolific base-stealer, and a near-.300-hitter.
The Dodgers interest in him made sense: they were a club with plenty of talent and it was reasonable to think swapping a young, unproven pitcher for a quality middle infielder would work to their advantage.
It didn’t.
DeShields struggled to keep his average at or below .250 each of his three seasons in Los Angeles. Worse yet, he promptly returned to his earlier form after signing with the Cardinals in 1996.
But what makes this deal so maddening for Dodgers fans is the fact that they gave up one of the greatest pitchers of all time just to rent DeShields’ subpar services for three seasons.
Pedro Martinez—who had a fine season in LA before being dealt to the Expos—would soon claim five ERA titles, three Cy Young’s during a four-year stretch, and become a legend in Boston sports history.
Those kinds of decisions are the reason why the storied Dodgers franchise has not won a postseason series since 1988.
San Diego Padres: Trading Ozzie Smith to St. Louis
28 of 30
When: 1981
In Exchange For: SS Garry Templeton, OF Sixto Lezcano
Garry Templeton had a pretty solid career. He led the NL in triples three straight seasons, went to three All-Star Games, and was a regular starter in the San Diego infield for virtually the entire decade of the 1980s.
But he wasn’t Ozzie Smith.
Smith, who was already a two-time Gold Glover when the Padres traded him to St. Louis, soon became the game’s greatest defensive shortstop, and eventually turned himself into an accomplished hitter.
Any time a team deals away a future Hall of Famer, it’s going to seem like a blunder.
But because Smith became such a beloved figure in both St. Louis and in the game’s history, this move was exceptionally misguided.
Arizona: Trading Carlos Quentin to the Chicago White Sox
29 of 30
When: 2007
In Exchange For: OF Chris Carter
It’s not too early to declare this trade a major faux pas.
Quentin was the Diamondbacks first-round pick in the 2003 draft. Sure, his first two seasons in the big leagues were pretty disappointing, but didn’t they give up on him a bit too early?
The D-backs traded Quentin to the White Sox for Chris Carter, a promising minor leaguer, but a player who Arizona traded to Oakland just two weeks later.
It remains to be seen if Carter will turn into a quality player: he didn’t make his debut until last August.
But because Quentin has become an outstanding bat in the White Sox lineup (83 home runs in just 360 games) the Diamondbacks might be kicking themselves for the move…especially since they traded away Dan Haren, the player they acquired from Oakland in exchange for Chris Carter.
Colorado: Trading Darryl Kile To St. Louis
30 of 30
When: 1999
In Exchange For: IF Brent Butler, P Manny Aybar, P Rich Croushore, P Jose Jimenez
Because of his surprising and tragic death, Darryl Kile only had two full seasons in St. Louis.
But they were extremely productive. He won 20 games in 2000 and 16 more in 2001.
His performance during those two years was a major win for the Cardinals front office.
All they had to do to land Kile (as well as a pretty solid righty out of the bullpen, Dave Veres) was trade away a decent closer, two pitchers who didn’t finish the season in Colorado, and a utility infielder.
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