Cities Journal

20 Worst Trades In MLB History


Sometimes a trade backfires on an organization. And other times, a bad trade can set a franchise back 5 years. There have been hundreds of terrible, one-side trades over the years in Major League Baseball, but these are the 20 that baseball fans won’t soon forget.

1.  Derrek Lee

Marlins Trade Derrek Lee To Cubs For Hee-Seop Choi (2003)

I’ll never forget this trade and laughing at the Marlins because I saw Choi play regularly at AAA Iowa. Choi was a young power hitting lefty but it was clear he was a Quad-A player at best. Lee, on the other hand, well… yeah, he was good. Real good.

Lee was a World Series Champion with Florida in 2003, and he won the National League batting title in 2005. He was also a two-time All-Star selection, and won the Gold Glove Award three times. On the other hand Hee-Seop Choi played in 80 games in the 2003 season, hitting .218 with eight home runs and 28 RBI.

On June 7, 2003 he suffered a very nasty concussion following a collision with teammate pitcher Kerry Wood, went on the disabled list, and never reclaimed his starting role.

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  • Jeff Jones

    Apparently this writer has shortsightedness with baseball history. All of these trades except the Ruth trade happened within the last 20 years. I am a Cubs fan and do think the ARam and Lee trades were steals but they dont reach to the level of worst trades in history.Here is a list that could be counted as worse in history.Not all players are listed in trades.
    1. Nolan Ryan for Jim Fregosi
    2. Ryne Sandberg for Ivan DeJesus
    3. Lou Brock for Ernie Borgilio
    4. Pedro Martinez for Carl Pavano
    5. Jeff Bagwell for Lary Anderson
    6. Frank Robinson for Milt Pappas
    7. Christt=y Mathewson for Amos Rusie
    Most of these players are in the HOF or have the stats to be considered for induction. I bet there readers could come up with other trades that are worse than most listed in this article.

  • Overbrook

    You must be a Cubs fan…I could name 20 trades worse than the Derek Lee trade or the Aramis Ramirez trade. Let’s start with giving away Hall of Famers, like, oh, Lou Brock…..

    • DundeeU

      I kept waiting for the Lou Brock trade to come up. That trade was the very model of what a GM shouldn’t do! (And I can’t remember the name of the schlub the Cards sent to the Cubs.)

  • Mind Over Reality

    Neither of the Cubs trades listed was even the most one-sided in their history. That would be trading Ivan DeJesus to the Phillies for Larry Bowa and that Sandberg guy.

  • Jack

    Try this again with trades that propelled the team that fleeced to win World Series or multi World Series like the Orioles acquiring Frank Robinson.

  • Yoyo

    Ernie Brolio? Anybody heard of him? Lou Brock yeah the guy the stole 938 bases.

    • John

      That one crossed my mind as well. There’s also Ed Hearn for David Cone and Willie Randolph for Doc Medich that I’m surprised didn’t make the list.

    • Dan Ryan


    • CapitalistPig

      Not often mentioned–Lou Brock may be the worst defensive outfielder I ever witnessed. Weak, incredibly inaccurate arm–fast but never got a jump on a ball because he constantly misjudged the flight path, occassionally threw to the wrong base or didn’t look for the cut-off man. Weird, because offensively he had such great instincts. He better steal a lot of bases.
      Today, he would be the perfect player for the DH–& stadium security would be notified if he was caught anywhere near the playing field with a glove.

  • Ethbob21

    Kent Bottenfield for Jim Edmonds?

    • CubFan

      Bottenfeld AND Adam Kennedy. All the Angels got out of it was a World Championship.

  • Barry Kramer

    anyone remember the Astros getting Schilling, Harnish, and Finley for Glenn Davis who did zip for the O’s

  • toody

    Ryne Sandberg for Ivan Dejesus

    • Dan Ryan

      The Cubs got that one right.

      • Travis Jerde

        Yes they did, and got a serviceable Larry Bowa and Gary Matthews in that trade too, right? Anyway I think toody is making the case that the Phillies made the worst trade on that one.

  • redsoxu571

    Those “few extra bucks” the Red Sox got for Ruth was, at the time, easily the largest sale of a player in sports history (and also a massive amount of money). If you read contemporary writings on the subject, you’ll also see that Ruth (outside of his diva lifestyle and dangerous living habits) was very upset about his contract situation and wanted more money than Boston could give him. The “sale” of Ruth was really the modern equivalent of a smaller market team letting a huge star go when the team could no longer afford to pay him as desired. They actually got a pretty good return considering their lack of leverage; the swap only looks terrible because the money value doesn’t look like much today and because of the myths surrounding the sale.

    • angelo317

      All quite true…and it was STILL a hideous trade! Think of everything that might have gone differently if the Sox owner had the $$ for that play he was producing (was that later debunked as urban legend? not sure, honestly). Maybe Ruth never becomes an OF and remains a pitcher (probably becoming the best ever). Who knows what becomes of the Yankees? Possibly changed the history of 2 major MLB franchises (and the league overall).

      • Scott

        He “probably becomes the best pitcher of all time?” Wow…talk about ridiculous and ignorant statements.
        You DO realize that Boston is the team that moved him to the OF, right? And they did so two years BEFORE they traded him to the Yankees. That there were a number of reasons why. 1-He wanted to play everyday.

        2-It was during WWII and many players were fighting, leaving teams like the Red Sox short of players.

        3-He injured his hand before his start in the World Series and walked 7 and gave up 6 hits.

        But…aside from all that, suggesting that he even might have become the greatest of all time is so goddamn ridiculous it’s not even funny.

        • TheGodThatFailed

          I can tell you one thing; it wasn’t WWII. Ruth was traded in 1920 and retired in 1935. So no, it wasn’t at all during WWII. Also, in 1918, he did indeed give up 7 walks. He also allowed 13 hits while giving up just 2 runs over 17 innings. Clearly it was a different era. So I’d argue that those 2 things didn’t have much to do with Ruth moving to outfield.

          More probably, he was emerging as a hitter and the Sox themselves wanted him playing every day as well.

          • Scott

            Sorry, I guess I just assumed anyone who had a rudimentary knowledge of history would have been able to figure out I obviously meant WWI, not WWII. That was a typo. My fault. Still…should have been pretty obvious.

    • Bill

      The swap looks terrible because of what Ruth became. He was a great pitcher with the Red Sox. He became the game’s all time greatest player with the Yankees. It has little to do with the amount of money exchanged. As you say, 100k was more than a significant chunk of change for a player at the time.

  • redsoxu571

    What a strange list…
    Alex Rodriguez for Alfonso Soriano? Considering all the “great player for garbage” trades in MLB history NO deal that involved each team getting something good should be on this list. So let’s get this straight: the Rangers couldn’t afford Rodriguez’s contract, and probably knew Rodriguez could get caught for steroids at any time (he was traded once testing was set to begin after 2003), and yet still manged to dump a huge chunk of his contract and get a player in return who was an All Star in both is Ranger seasons?

    Meanwhile, Konerko for Cameron, is that a joke? News flash: Konerko was worth 26.0 WAR for his career (three seasons above 3.0). Cameron was worth 49.7 (8 seasons above 4.0). Just because you don’t understand the value of defense doesn’t mean you should ignore it completely.

  • angelo317

    How is it possible that Nolan Ryan for Jim Fregosi is NOT on this list? Did I miss it?

  • resty sapuan

    Jason Varitek and Derek Lowe for Heathcliff Slocum. That deal turned two franchises completely in opposite directions.

    • Steve

      I don’t know about that. Seattle got to the ALCS in 2000 and 2001 and had two 903 win seasons in the two seasons after. Was a bad trade for them in 1997, but it didn’t ruin them.

    • D_Hawk

      Yep…that one sucked. I think the Ken Phelps for Jay Buhner was more lopsided, though.

  • Bill

    It did. It is number 15.

  • Bill

    Danny Cater for Sparky Lyle. Too many on this list are not actually horrible trades.

  • pjmcdon9960

    Umm, Tom Seaver???

    • John

      I need to clear up one ofthe most popular misconceptions in New York Mets
      history: That the Seaver trade was a bad trade.

      When Pat Zachry’s stats
      with the Mets (41 – 46 in 135 games with a 3.63 ERA) are compared directly to
      Tom Seaver’s with the Reds (75 – 46 in 158 games with a 3.18 ERA), Seaver’s are
      unquestionably better. However, the Mets also got a starting left fielder who
      was the runner up for Rookie of the Year in 1977 (Steve Henderson) and a Gold
      Glove second baseman (Doug Flynn).

      Also, the teams Zachry and Seaver
      respectively pitched for needs to be taken into consideration. While Seaver had
      the “Big Red Machine” behind him in Cincinnati, Zachry pitched for a team that
      consistently finished last in the NL East.

      Jerry Koosman managed to only
      compile a 11 – 35 record with the Mets in 1977 and 1978 before they mercifully
      traded him to the Minnesota Twins. His first season in Minnesota, Koosman
      returned to his 20 game winning form. It raises question as to how Zachry would
      have faired with a better team behind him, and how Seaver would have fared had
      he stayed in New York during that dark time in team history. Is it a stretch to
      believe that the 34 more wins Seaver had over Zachry might have been
      considerably lower were he not pitching to Johnny Bench?

      The final
      point, and perhaps the most important one is that these are questions that
      cannot and will never be answered. It remains a question, and Seaver’s legacy
      with the Mets is preserved by a trade that sent him out of New York. Jerry
      Koosman will never be wearing a New York Mets hat in Cooperstown, and perhaps he
      would be if the Reds were more interested in a lefty starter.

  • Brent Wit

    Trading Aroid and his overvalued salary wasn’t that bad of a trade.
    Also, you forgot one of the worst in MLB history that was always typical of the Red Sox – Jeff Bagwell for Larry Anderson!

  • Jeff Sullivan ✌

    Even after reading through the comments, can’t believe Jay Buhner has not been brought up!!!

  • evan

    if your responsible for any of these trades in your favor this should be labeled best trades ever

  • eglooney

    The Baines deal was bad; not because the Rangers gave up Sosa and other talent, but because they got a guy that didn’t want to be here – a loser – a whiner – a malcontent. Sosa was never going to be great until he started juicing and Canseco, at that point, hadn’t yet been a Ranger.

    They made the same mistake with Lee Mazilli (a much worse trade because Maz was marginal, at best, on top of not wanting to leave NY). Then, they compounded THAT mistake by adding real talent going the other way.

    And, who’s to say Smolzie would have had the same success in the different environment that was the Tigers? In Atlanta, he settled into place with a couple of HoFers – not to mention a great pitching coach. I don’t think the Tigers regret the trade so much as wonder why they couldn’t turn a Smolz into a HoF candidate.

  • Kevin Green

    Konerko for Cameron was in 1998 and it paid dividends because that netted them Ken Griffey, Jr. in the 2000 trade. And Duffy for Foster was in 1971 not 1977. A key 1977 trade was the one that sent Tom Seaver to the Reds . And where is the Ernie Broglio for Lou Brock trade? Do ya research, folks!

    • D_Hawk

      Yep…it’s like he didn’t even realize that Cameron was traded again. Thought his career ended shortly after the initial trade.

  • Corey Polis

    no Jeff Bagwell for Larry Anderson?

    • MeHoff, Jack

      Or Schilling and Brady Anderson for the immortal Mike Boddicker!

  • Alex Yamach

    This writer missed a few bad ones. Cubs trade Lou Brock to the Cardinals for Ernie Broglio – Phillies trade Ferguson Jenkins to the Cubs for Adolpho Philliips – Phillies trade Ryne Sandberg as a throw in to the Cubs for Ivan DeJesus – Cardinals trade Steve Carlton to the Phillies for Rick Wise –

    • JT

      He also put some in there that made no sense like Rodriguez soriano

    • CubFan

      The Cubs got Fergie Jenkins for Adolfo Phillips? Geez, I always thought it was for Larry Jackson.

  • Jace Curioso

    Ruth wasn’t trade, he was sold by the owner. The manager and coaches had bno say in the matter. Thank you No, No, Nanette!

  • chipster22

    This is actually MLB Worst Trades of the Last 30 Years, with a couple of oldies thrown in ………..

  • nuwriter

    The Reds trading Christy Mathewson to the Giants for Amos Rusie.

    Rusie, a Hall of Famer for his work with the Giants, pitched a total of 22 innings with the Reds, giving up 21 runs.

    Mathewson then went on to win 372 games for the Giants over 17 seasons with the Giants.

    Then, to make matters worse, the Reds got Mathewson back from the Giants in 1916, only to pitch one game and give up 8 runs in 9 innings. At least he won that one. Beating the Cubs 10-8.

  • Benny

    If you eliminate the Yankees, teams win the World Series about once every two or three decades—maybe. The Tigers were a perfect example in ’87. They went for it and got a guy who pitched great and just missed getting them there: Doyle Alexander. They gave up a prospect who turned out good–big deal. The Tigers were terrible in the 90s and Smoltz might’ve been just as bad in a park that was perfect for left-handed hitters. Please, no more idiotic articles about how this was a bad trade. It’s like reading a box score of yesterday’s game and saying the losing team should’ve used a different line-up.

  • Michael

    Frank Costanza would love to discuss the Jay Buehner trade with you. :)

  • Mike B

    Mike Cameron put up about 40% more WAR over his career than Paul Konerko.

  • agenteightysix

    It wasn’t “Dodgers scouts” who thought Pedro Martinez was too small to be an effective starting pitcher. It was their manager, Tommy Lasorda. Largely because of his gift of gab, Lasorda is a Dodger legend, so someone put forth the “Dodger scouts” story.

  • Stan DaMann

    The Cubs traded Rafael Palmeiro and Jamie Moyer to Texas for Mitch Williams. The Cubs also traded Lee Smith to Boston for Calvin Schiraldi and Al Nipper. Schiraldi was on the mound in the last inning of Game 6 of the 1986 World Series, and let the Mets win it. The Cubs also traded Bill Madlock in his prime for Bobby Murcer at the tail end of his career. Madlock had already won one batting title and went on to win a few more, as well as a World Series. How ’bout dem Cubbies??

  • The big A

    The Diamondbacks should have made this list. They traded half their team for Richie Sexton and only got 11 games out of him before he got hurt swinging his power stroke. (That was the year Randy Johnson threw a perfect game, but also lost 100+ games

  • Thomas Donohue

    How is Babe Ruth 5TH?

  • Gorgonzola Albatross

    Just for the record, Sosa hit a few HRs with teams other than the Cubs, so it was not exactly over 600 with the Cubs.

  • Adonis

    #10…10 years later, who is going to play for the Yankees this year?

  • Alex Holliday

    As a life long Yankees fan, they got the A-Rod one backwards on this list.

  • Rich Basile

    1988 – Yankees traded Jay Buhner for Ken Phelps,

  • keggler

    More recently the Mariners traded Adam Jones, Chris Tillman and George Sherrill to the Orioles for Eric Bedard. The three traded have made a combined 5 All-Star appearances while Bedard had a couple of mediocre years in Seattle.

  • rickterp

    Um, where’s Bronson Arroyo from the Red Sox to the Reds for Wily Mo Pena? And how about Jason Varitek and Derek Lowe from the Mariners to the Red Sox for Heathcliffe Slocumb?

  • Nolan Lees

    Another suggestion: Brandon Phillips, Cliff Lee and Grady Sizemore for Bartolo Colon right before Colon stopped being an elite pitcher. Not every day you see a team trade away THREE future all-stars in one deal. Might have been the nail in the coffin for baseball in Montreal.

  • ralph_indianapolis

    Usually with these lists modern trades (events) get more attention. But if you use the term “of all time” I think that means all eras should be considered the same way.

  • golflaw

    Frank Robinson for Milt Pappas was the worst. Reds owner Bill DeWitt said at the time “Robinson is an old 30”. Yea, so old he won the Triple Crown the next year and Orioles won the World Series. In 4 as I recall.

  • Draker

    I think the Giants trading Gaylord Perry to the Indians for Sam McDowell has to make the top 10. Perry went on to a couple of Cy Young awards and the Hall of Fame while McDowell was out of baseball after a couple of wretched seasons in SF.

  • Lou Takacs

    Lou Brock for Ernie Broglio? Nolan Ryan for Jim Fregosi? Ryne Sandberg for DeJesus? Jeff Bagwell for Larry Anderson? ALL of these are worse than MOST that you’ve listed here–get a baseball history book, turkey.

  • Raul

    You missed Seattle trading 3 All-Stars and 2 or 3 prospects for Erik Bedard from Baltimore

  • SZ4L

    Adam Jones, Chris Tillman, George Sherrill, Kameron Mickolio and Tony Butler for Erik Bedard? That’s not on the list?

    And the A-rod for Soriano trade really wan’t that bad, the Rangers couldn’t afford to give that much money to one player at that time.

  • Reggie91

    The Marlins trading Cabrera to the Tigers would Andrew Miller and Maybin has to be a top 10 of all time!!

  • MEBears

    Derek Lowe and Jason Varitek for Heathcliff Slocumb doesn’t make the list? And Babe Ruth wasn’t traded, he was sold.

  • David Gee

    Funny thing about Mike Cameron is that later the White Sox traded him to the Mariners for Ken Griffey Jr. and the Mariners actually got more out of Cameron than the Reds did out of Griffey.

  • Guest

    Lee got traded from the Cubs due to personality issues. They were lucky to get a sack of potatoes given it was known they wanted to upload him.

  • mm

    Steve Carlton for Rick Wise

  • guest1xprq11

    Giants trade Gaylord Perry and Frank Duffy for Sam McDowell.

  • CubFan

    Ron Perranoski for Don Zimmer.

  • Dan Ryan

    Brock for Broglio has to be the worst/best trade ever #cubs #cardinals

  • cliffy44

    Trading one of the best first basemen in the history of baseball (Keith Hernandez) for one of the worst announcers (also Keith Hernandez) in the history of baseball.
    SNY should trade Hernandez for a cotton candy vendor, with the option to sell hot dogs in the parking lot, during rain delay.

  • Ryan

    Ernie Broglio!!!!!!!!!!!!!!!

  • Travis Jerde

    It seems that it is very difficult to compare many of these modern trades with those of past years. While the trades pre-1980s or so may be genuinely poor, one-sided trades, many of the modern ones had money as the cause–that is to say the trading “loser” wasn’t going to be able to sign said player anyway, and tried to get something for the player involved rather than letting them go to the off-season as a free-agent, and get nothing at all. This is in contrast to the “old” days when the trades were meant to improve both teams, and one team clearly was the loser in the deal.

  • Rick Eger

    Here’s one…..St. Louis trading Steve Carlson too the Phillies for Rick Wise.

  • Rick Eger

    Babe Ruth to the Yankees for 125,000 dollars.

  • Peter Stumpf

    This is one of the 16 worst sports lists in history

  • David

    The worst trade of my lifetime was the Astros giving up Joe Morgan, Cesar Geronimo,Jack Billingham and Dennis Menke for Lee May and Tommy Helms of the Reds. This created the big red machine. That has to be top five.

  • ronbobel777

    indians trade rocky colavito for harvey kuehn.

  • David Buchman

    How is the Miguel Cabrera trade not on there? The Marlins got Cameron Maybin, Mike Rabelo, Burke Badenhop and Andrew Miller.

  • Frank__Grimes

    A-Rod is considered one of the best players in the game?
    How is brock for broglio not there?

    Sandberg for DeJesus?

  • Michael Castellano

    The writer did very poor research when he made up this list. Missing was Fergosi for Nolan Ryan and perhaps the worst trade of all time, the Mets traded Harry Chitti for Harry Chitti!, a favorite story Ralph Kiner used to tell. He listed Babe Ruth, but that deal was for cash, and was not a trade.

  • KobraKai7474

    Come on. How can you write this article without Ryne Sandberg and Larry Bowa for Ivan Dejesus. As bad as that trade is on its face, it gets worse. The Phillies claimed to have done it to get a younger shortstop (DeJesus was allegedly 29 while Bowa was 38), but DeJesus’ numbers and defensive range tailed off almost immediately thereafter, leading most to believe that he had been lying about his age and was actually pretty much the same age as Bowa. In the end, both Bowa and DeJesus played 3 more years as a regular shortstop after the trade with similar stats before becoming bench players. And Sandberg… well, he might have went to an all star game or 10 and maybe gotten himself elected to the hall of fame…. oh yeah, he is also widely considered to be the best second basemen to ever play the game.

  • KobraKai7474

    If they were going to list a Curt Schilling trade, how about Curt Schilling straight up for Jason Grimsley? Immediately thereafter, Curt Schilling turned into Curt Schilling, and Grimsley kept on being Grimsley, a fungible, back-of-the-bullpen guy.

  • NEdonn

    There are probably not a lot of Padre fans that would agree with his list.

  • Emily Bennet

    A couple of other missed ones: Cubs send Lou Brock to the Cardinals for Ernie Broglio in 1964; Giants sending Orlando Cepeda to the Cardinals in 1966 for Ray Sadecki. The latter one is a little more understandable. The Giants didn’t need Cepeda because they had Willie McCovey on first and Cepeda was coming off an injury, but it still didn’t turn out well. Cepeda was critical to the Cardinals’ 1967 World Series win; Sadecki was 32-39 in four seasons with the Giants. The Brock trade, of course, is one of the best or worst ever, depending on which side of it you’re on. Broglio went 7-19 in less than three seasons with the Cubs and then was out of baseball. Brock spent 16 seasons with the Cardinals, helping them to three World Series, ending his career with 938 stolen bases and more than 3,000 hits and was a first-ballot Hall of Famer. I feel like this one really should have made the top 16.

  • disqus_qOTkEBSbhm

    I think it’s hilarious that this list includes two lopsided Cubs trades in the list of word trades in history, and neither one of them are Larry Bowa and Ryne Sandberg for Ivan DeJesus or Lou Brock for Ernie Broglio(a trade so awful that it spawned a phrase used to describe terrible trades).

  • oldjohn

    Lou Brock for Ernie Broglio was the worst trade of all time.

  • robb32

    Sorry. the Red Sox sale of Ruth to the Yankits IS the #1 worst of all time…altho the Jackson trade is among the top..

  • CapitalistPig

    I take a bit of issue with a few of these–I saw Sammy Sosa when he came up from the minor leagues with the Rangers along with a kid by the name of Rueben Sierra. Both those kids came up as skinny, wiry, not real big, but go get em fast outfielders & good contact hitters with occasional power–probably 15 to 25 homers a year with lots of gap doubles & triples. Good young players. They traded Sosa, which I wasn’t thrilled with but several years later he re-emerged with the Cub & I could not believe what I saw–that same guy had gotten so rocked up & ripped up & put on so much pure muscle mass thought he was doing pro body building on the side.
    Turns out–he was cheating. It’s a little hard to blame an organization like Texas for trading a guy who, in essence, cheated to get the numbers he put up. The sad part is, Sosa would have had a very successful, long career though I can safely say probably not a HOF career (not that he’s going to get in now anyway.)
    As to the Smotz trade, Detroit knew they were trading away a very good but not quite ready for the majors pitcher to get an aging but still very effective Doyle Alexander (Dr Hook was his nickname because he had such a good curve). Detroit went on to win the World Series that year with a Alexander a big contributor—I’ll trade a young pitcher that I KNOW will be a HOFer every single year for a World Series ring. The goal is to win championships–not collect players & stats.

  • Hokeybob

    Where is the Nolan Ryan trade in this? Dude- wtf, the Mets traded him for some nobody third baseman and he turns out to be one of the greatest pitchers to ever step on the mound.

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