Baseball Trades That Still Sting

Last Updated: August 28th, 2026 by Shaiel Ben-Ephraim

There are a lot of baseball trades that really still sting, but we have to think of it from the perspective of the people at the time. Every one of these looks so obvious now, but they didn't look obvious then; well, most of them didn't anyway.

The question that's interesting isn't how they could be so dumb, but what they were trying to solve. Every case here had a real problem that the team that got fleeced was trying to solve, but they used the wrong currency to try to solve that. You can sort of put these into three different categories. The ones who are trying to win now and then trade a kid for a rental; we see a lot of those still. We see ones where they misread the body; they didn't know what they were getting- the players too old, too tall, and very often going to be too injured.

And when they were trying to get rid of a person rather than a player, they wanted to get rid of a contract; there was some kind of personal feud; they thought there was some kind of problem with the attitude; and maybe the problem was with the person who did the trade. 'Cause look, nobody trades a Hall of Famer on purpose; they trade a problem, but very often you get a much bigger problem.

26. Babe Ruth From The Boston Red Sox To The New York Yankees

This is the big one, probably the worst trade of all time, but it's actually really easy to understand why this happened. Harry Frazee had no money, it wasn't a baseball decision at all, he needed money in order to get his mortgage on Fenway Park.

Look, the Babe Ruth trade is probably considered the worst trade of all time, but it's actually pretty easy to understand what happened. Harry Frazee didn't have any money; he owed quite a bit. The Yankees had money, so he got $100,000 in $45,000 installments, and separately he got a $300,000 loan secured by a mortgage on Fenway Park. And he wanted to get rid of Babe Ruth.

Ruth had just hit 29 homers, which was certainly something that seemed like an aberration at the time, and he immediately wanted his salary to be doubled. Today we look at Babe Ruth as colorful, but he was really something; he was impossible to manage, basically a man-child. So it seemed like a good way to get rid of a problem, a very talented problem, and solve all the cash problems that the Red Sox had.

There was really no way of knowing in advance that Ruth wouldn't just continue to hit home runs. He would completely change the sport and redefine it. You can't predict that sort of thing.

So look, the Babe Ruth trade is considered to be the worst trade of all time, and in many ways it probably is. But it's not that hard to understand why it happened. Harry Frazee, owner of the Red Sox, didn't have any money; the team wasn't dead; he owed a lot. He got $100,000 in 425,000 installments; he separately got a $300,000 loan and got that through a mortgage on Fenway Park.

And there's this myth that the money went into a Broadway play that was a failure, No, No, Nanette, but that is a myth twice over. Not only did that show appear years later, but it was also a great big hit.

So from Frazee's perspective, he wanted to get rid of Ruth, because Ruth, who we think of today as a Charming Legend, was a real handful, and some might even call him locker room poison. And he hit 29 home runs and immediately asked to double his salary, and there was no way you could expect him to continue to do that. That seems like a total aberration at the time. It's difficult to predict someone completely upending baseball, but that is exactly what happened.

25. Frank Robinson From The Reds To The Orioles

Now, the Frank Robinson trade from the Reds to the Orioles is also known as one of the worst trades ever made, and it was awful, but it also has a twist, so hear me out. Reds GM Bill DeWitt said Robinson was an old 30; he'd had injuries, and he had some trouble off the field. They knew he had a couple of good seasons left in him, but they wanted to get some young talents: Milt Pappas, Jack Baldschun, and Dick Simpson, and Pappas was the main element here. He was a legitimately good young star who was supposed to solve some problems in their rotation. Now we all know how that ended.

Robinson won the Triple Crown the next year, hitting 316, 49 homers, 122 RBIs, getting an MVP, and became the first player to win the MVP in the American and National Leagues. Baltimore won the World Series, and they swept it, and he didn't decline for six more years.

Pappas, Simpson, and Baldschun were all busts. But the Reds had the last laugh because Baldschun was packaged with Frank Duffy and, in 1971, was traded to get George Foster. Foster, of course, is one of the cornerstones of the great Reds team of the 1970s. So even though this trade backfired massively in the short term, in the long term it helped Cincinnati do exactly what it was trying to do, which is rebuild with young talent. So what if it took a few years to get there?

24. Randy Johnson From The Expos To The Mariners

Look, if Randy Johnson had stayed with the Expos, everything might have been different. They might still be in Montreal. But it's not difficult to understand why this one happened either. Montreal was going for it, and they wanted to get Mark Langston, who was a proven ace and a rental, to help them make that final push.

Seattle, in exchange for him, got not only Johnson but also Brian Holman and Gene Harris. Now the Randy Johnson of that time was very unlikely to become the Randy Johnson that we know and love. At 25, he looked like a science experiment. He had weird mechanics, and he walked people far more than was even remotely acceptable.

One of the things that people forget about this trade is that Langston was a gem for Montreal after the trade. He pitched 12 and 9 and had a 2.39 ERA and 175 strikeouts. He did everything that was expected of him. It's not his fault that they missed the playoffs. He did his job. Of course, he walked as a free agent to the Angels after that.

Unfortunately for Montreal, aside from that, Johnson also figured out his delivery and became a five-time Cy Young winner with 4,875 strikeouts. So Montreal got 4 months of a good pitcher and paid for it with one of the best pitchers of all time. But they really had no way of knowing. It was an honest mistake and a fairly good bet, but an absolutely lethal one.

23. Nolan Ryan From The Mets To The Angels

Now this one really hurts because I happen to be a Mets fan. But it's not that hard to figure out why the Mets traded Nolan Ryan in 1971. I mean, talk about a team that had pitching to spare: Seaver, Koosman, Gentry, Matlack. They had trouble in the infield, and they needed a third baseman badly. Jim Fregosi was a six-time All-Star, and they thought they could move him successfully to third.

Meanwhile, Ryan showed a lot of promise but a lot of indications that he would never fulfill that promise. We're talking about a 24-year-old who was very wild and deeply unhappy and was talking to some people in the Mets about quitting baseball.

The Mets thought they were getting rid of someone who was completely unfixable in order to get someone who would be a very important part of their lineup. There was really no way of telling that Fregosi was going to hit 232; that's very Mets, to get an All-Star with that and would be gone in a year and a half. And Nolan took a little time to get his peak, but in '73 he hit the all-time record of 383 strikeouts, got two no-hitters that season alone.

And what people forget about Nolan is he never solved the wildness problem. He actually led the league in walks eight times, but he got more strikeouts than he got walks. He got 5,714 strikeouts. So the Mets were right about the control problem; they were wrong about Fregosi, and they were wrong about the strikeouts.

22. Ryne Sandberg To The Chicago Cubs From The Phillies

Very often, with these trades, you can figure out what the team that was on the losing side was thinking, but in this case it's kind of hard to figure out why the Phillies sent Ryan Sandberg with Larry Bowa to the Cubs. And that's because a lot of the people in their farm system knew very well that Sandberg was special. One of them was the person who, at this point, was the Cubs GM, Dallas Green. He ran the Phillies farm system; he knew exactly what Sandberg was worth, and that's why he insisted that he'd be included.

But someone else who knew exactly what Sandberg was worth was Larry Bowa. Larry Bowa said that after being traded, when he found out that Sandberg was an afterthought in the trade, he was amazed because of the talent that kid had.

So Bowa and Sandberg were a package. Bowa was the star attraction there, and he played very well for the Cubs, and they also got Ivan DeJesus, the man of the future. There was no way of knowing that DeJesus would be as unremarkable as he was. That was a little bit of a surprise, but the truth is their own farm system knew how good Sandberg was. Getting rid of Bowa at 36 maybe made sense, so he had three more good years in him. And together, it's a complete disaster for their own farm system. The Phillies really should have known better.

21. Lou Brock From The Cubs To The Cardinals

Okay, the Lou Brock trade was one that really should have gone the Cardinals' way. On paper, they definitely got the better of that. Ernie Broglio was 18 and 8 the year before; Lou Brock was hitting 251 as a 24-year-old outfielder. He couldn't field very well and struck out a lot. The Cubs were ecstatic with this trade, and with good reason.

But there was something that nobody knew, which was that Broglio's arm was shot. He had a UCL tear, which at that time couldn't be diagnosed without surgery, so nobody knew. And there was no Tommy John surgery at the time, so he went 7 and 19 for the rest of his career and was done.

Meanwhile, Brock hit 348, the Cardinals won the World Series, and he had the record for the most stolen bases until Rickey shattered it with 3,023 hits. And this is just one of those mistakes where luck does it all, and the fans of the team that lost the trade were absolutely ecstatic with it until they realized what had happened.

This one, I really feel for the Cubs, cuz they did not make a mistake on paper. Everything broke wrong, literally.

20. John Smoltz From Detroit To Atlanta

The Smoltz trade for Doyle Alexander is incredibly lopsided, and we all know why. Doyle was a rental, and of course Smoltz is a Hall of Famer. But again, at that time Smoltz was 20 years old, in Double-A with a 5.68 ERA, and Doyle came in and did exactly what the Tigers wanted him to do. The guy went 9-0 with a 1.53 ERA. Detroit won the division. Sure, they lost the ALCS, but couldn't have asked for more from Doyle.

And at first, not only did it look like Doyle had done his job, but also Smoltz was looking like a head case early on. He debuted for the Braves in 1988, but he had a 5.48 ERA. In 1991, at the All-Star break, he was 2-11 with a 5.16 ERA, and that's 4 years after the trade. He talked to a sports psychologist who managed to straighten him out, but that turnaround was very unexpected. He even said this about himself, he said anytime things started to get a little hairy I would begin to unravel.

So betting on Smoltz was not a rational thing to do to begin with. Doyle did everything that was expected, and Detroit seemed to have won that trade for years. But in the end, that's not how it turned out.

19. Ozzie Smith From Padres To Cardinals

Now here is another one that really made sense at the time. Gary Templeton was a much better hitter than Ozzie Smith. I mean, Ozzie Smith was always a fairly mediocre hitter, but what led to the trade was when Gary made an obscene gesture at the Cardinals fans, and Herzog stormed at him, and the players got between them. He said if they hadn't happened, quote, "I guess we'd have had a pretty good fight."

Templeton was fined 5,000, and Herzog wanted him out. Smith had a no-trade clause, and that caused a lot of problems, but the trade went through.

Now, sure, Ozzie Smith is the greatest defensive shortstop who ever lived, right? 13 straight Gold Gloves, 15 All-Star selections, the backflip, 1982 title, Cooperstown, the whole thing. But Templeton was injured right after the trade. We're talking about opening day 1982, and he had arthroscopic surgery in March 1983. He had seven knee operations after that, and for a switch hitter, that is a massive blow because he couldn't plant and turn.

His left-handed swing never came back, and he just wasn't the same player. So he also hit around the 250s after the trade, but there was no way of knowing that. This is a combination of a behavior issue and an injury issue.

18. Miguel Cabrera From Marlins To Tigers

The Marlins always do the same thing: they make their trades in order to save money, and that's why they gave Cabrera to the Tigers with Dontrelle Willis. In exchange, they got six perfectly decent players like Cameron Maybin and Andrew Miller, who were recent first-round picks, and the idea was you get quantity for quality and hope that they pan out. But not only did Cabrera end up being a back-to-back MVP, 2012 Triple Crown guy, first in 45 years, but the prospects didn't really work out for the Marlins.

Part of it is because they moved on too fast and didn't develop them properly. The best example is Andrew Miller, who became a fantastic reliever, dominant in the playoffs, but not for the Marlins. They again moved on too quickly because they didn't want to pay anyone what they deserved.

17. Glen Davis To The Baltimore Orioles For Steve Finley, Pete Harnisch, And Curt Schilling

Quantity for quality doesn't always work, but sometimes it does. Take the trade of Glen Davis for Curt Schilling, Steve Finley, and Pete Harnisch.

So Davis was a big star, but once he got to the Orioles, he damaged his spinal accessory nerve in spring training and never really was the same. In 1993, he had his jaw broken in a bar fight and was hitting 177.

Meanwhile, Curt Schilling went on to win three World Series and become the Bloody Sock legend, and he wasn't even the only All-Star in that package, because you had Finley who won Gold Gloves; you had Harnisch who was an All-Star.

Even if Davis had continued to be Davis, that would have turned out to be a bad trade, but what really caps it off as one of the worst of all time is that even Davis stopped being Davis very quickly after.

16. Pedro Martinez To The Montreal Expos For Delino Deshields

We all know why the Dodgers traded Pedro Martinez, it's because he was 5 ft 11 and 170 lb and they thought that with all the talent in the world he wasn't strong enough to survive a starter's workload, so they decided to make him a reliever or trade him. They ended up trading him for Delino DeShields, a good everyday second baseman, something the Dodgers really needed at the time.

Now we all know what happened. Pedro went on to win the 1997 Cy Young Award in Montreal; his time with the Red Sox is one of the greatest stretches by a pitcher ever, and his time with the Mets was also very impressive. DeShields did his job for three seasons; he hit 241. He was okay, no Pedro.

It's probably important to remember that talent is more important than body every time.

15. Mark McGwire From Oakland To St. Louis

The McGuire-to-Cardinals trade mostly stung because of what happened right after: the year afterward, McGuire broke the Home Run Record, became an absolute cultural phenomenon, and that embarrassed the A's deeply. But you have to remember that McGuire was saying that he was not going to resign, so it was definitely worth it to trade him for something instead of settling for nothing. They got TJ Matthews, Eric Ludwig, and Blake Stein.

None of that really worked out, but it's not like McGuire was going to stay. It made perfect sense to trade him, but that didn't stop the A's fans and the top brass from feeling incredible pain when they saw what came next.

14. Joe Morgan From Houston To Cincinnati

Every now and then, the problem with a lopsided trade is racism, and that was the case with the 1971 trade of Joe Morgan. The Astros thought of Morgan as selfish, moody, and a troublemaker. Yes, that is Joe Morgan, one of the best second basemen who ever lived, the leader of the Reds, the top team of the 1970s.

Morgan had a different version, and I believe him. He said in his memoir Walker was a racist who treated black players like children incapable of thinking for themselves. And Walker also was one of the people who tried to boycott Jackie Robinson, so it stands to reason that that is what is behind it. And racism doesn't pay.

The Astros got Lemay and hit 39 home runs, and they got Tommy Helms, and they must have thought at first that they got the better of it, but they certainly didn't. Not only did Cincinnati get Morgan, but they also got Cesar Geronimo and Jack Billingham in the same trade. That's three starters of the Big Red Machine, the team that was the absolute best of the era. Morgan won back-to-back MVPs.

And so Houston traded away what they thought was a difficult personality, but they gave the Reds a dynasty. And of course the Astros in the 70s, not quite at that.

13. George Foster From The Giants To The Reds For Vern Geishert And Frank Duffy

The George Foster trade certainly seems unfortunate in retrospect, but if you were the Giants in 1971, you'd be doing the same thing, because you'd have three outfielders: Bonds, Mays, and Henderson, and that quality speaks for itself. Foster was a 22-year-old, hadn't quite hit yet, didn't seem to be on the verge of greatness, showed promise, but that's about it. They hoped that Frank Duffy would be the shortstop of the future cuz they certainly needed one. They also got Vern Geishert thrown in as well.

Now Foster, as we know, went on to be a legend: he hit 52 home runs in 1977, the only one to hit 50 until Cecil Fielder did it in 1990, and he won an MVP. Duffy play 21 games before being flipped, Geishert didn't pitch at all.

Now it gets worse because Duffy becomes part of the trade that lets Cleveland take Gaylord Perry, and San Francisco got back a pitcher who wouldn't do much in that trade. So he had one trade, and then another of two Hall of Fame-caliber careers going out the door, and they got absolutely nothing back.

Now the funny part is that the Perry trade and the Morgan trade happened on the same day, in the winter meetings in Phoenix. That was a very bad day for some of those teams. So the Giants had too many outfielders, and they wanted to solve that problem, and ended up passing on one of the absolute best players of his generation.

12. Fred McGriff From San Diego To Atlanta

The McGriff trade is a bit of an outlier here because we're not talking about a mistake; we're talking about a legit fire sale. San Diego was tearing down the entire roster for payroll reasons; they knew that McGriff was a fantastic player, but they just couldn't afford to keep him. Atlanta was nine games behind the Giants; they really needed McGriff to catch up, and boy did it work. Atlanta went 51 and 17 the rest of the way, and they caught the Giants.

And the most amazing part people will remember is McGriff's first night in uniform: the press box at Fulton County Stadium caught fire before the game, then he homered. That is real drama. He caught fire, the team caught fire, the press box caught fire. But I don't think any of that, well maybe the fire, what a surprise, the Padres too much, they just needed to get rid of the payroll.

The Trade:

11. Jeff Bagwell From Boston To Houston

Sometimes the problem is just a lack of imagination. The Red Sox had Jeff Bagwell coming up in Double-A; he was hitting very nicely for average, not for power. The Sox thought he would make a very good player, but they had him down as a third baseman, and they felt that he was completely blocked by the great Wade Boggs. And one of their scouts said he would never play a game at third base in the major leagues, at this rate. And that was correct. He was traded to the Astros. The Astros realized they could easily make him a first baseman. He became Rookie of the Year and VP, hit 449 home runs, and is in the Hall of Fame now.

To be fair, the Red Sox had a real need; their bullpen was awful, and they were in a pennant race, so they got Larry Andersen, 37, one of the best setup men in the MLB. He pitched all 22 innings for the Sox, and they got swept in the ALCS, and he left as a free agent. So this one is a lack of imagination; if they had only understood that Bagwell could have been switched to another position, everything would have been different for the Sox.

10. Yordan Alvarez To Houston For Josh Fields

Now, to be fair, the Dodgers have enough hitting power so they can probably live with the fact that they missed out on Yordan Alvarez, but still, this is one of the most hilariously painful trades on an objective level. The Dodgers had just gotten Alvarez out of Cuba for 2 million dollars and hadn't seen him play. They really needed bullpen depth for the playoffs, so they wanted to get Josh Fields. Fields was a very good reliever; Alvarez was 19 years old. It made perfect sense to get him.

Now we all know what happened with Alvarez. Alvarez has been one of the most feared hitters in baseball since, maybe the best hitter in the game, now unanimous Rookie of the Year in 2019, just an absolutely incredible player. But what's interesting, and less people know about, is what happened with Fields.

Fields was fantastic for the Dodgers. He held hitters to a .194 average in 2017, striking out 60 in 57 innings. He did everything that he was asked to do, but then there was the 2017 World Series, where they played, of course, the Astros. Fields came on in the top of the 10th inning of game two, gave up back-to-back home runs to Altuve and Correa, and then a double to Bregman, and he was pulled without recording a single out. Astros won that game and went on to win the series in seven. The only thing that would have made that more bitter for the Dodgers is if Alvarez had hit the winning hit.

The Impact:

The Outcome:

9. Heathcliff Slocumb To Seattle For Jason Varitek And Derek Lowe

The Mariners had an absolutely incredible offense but not the best bullpen. They were leading the American League with 925 runs and set a record with 264 homers. Griffey won the MVP with his 56 homers; Randy Johnson went 20- 4, but they decided that they needed to improve their bullpen.

The price for Heathcliff Slocumb was Varitek, who was at that time a 25-year-old AAA catcher who was blocked by Dan Wilson, and Lowe, who had just gotten shellacked in his debut season. Neither one of them looked like much, so Slocumb went. It didn't work at all. Slocumb's 4.97 in Seattle didn't contribute at all. They lost the ALDS to Baltimore. And the pitcher, Lowe, and catcher Varitek helped Boston end the Bambino's curse.

So a team with Griffey, Edgar, A-Rod, and Randy Johnson panicked and sent away two players who could have been cornerstones of their future. Big, big mistake. The result of panicking.

8. Keith Hernandez For Neil Allen And Rick Ownbey

If there's one case where the team trading away that got fleeced knew exactly what they were doing and who they were losing, it's the Keith Hernandez trade. No one can accuse Whitey Herzog of not knowing baseball, and he traded away Keith Hernandez, the co-MVP with a gold glove who just helped them win the World Series, because of a clash of personalities and his cocaine use, which would continue to be a problem.

Hernandez went on to do with the Mets what you would expect him to do. He became the leadership spine, won the 1986 World Series, and continued to rack up gold gloves.

Now, for St Louis, the trade looked like a big mistake at first. The next year after trading him, the Champs went 79 and 83, but they got Jack Clark in a trade. He ended up replacing Keith with even better hitting. The Cardinals went on to continue winning, so in the long term it didn't matter, but the Cardinals and the Mets ended up being exceptional. We'll never know how good the Cardinals would have been if Keith remained, but if Herzog didn't want him, he probably knew what he was doing.

Ultimately, this is one of the few cases where a trade this lopsided didn't hurt the team that came out on the losing side.

7. Tom Seaver For Pat Zachry, Doug Flynn, Steve Henderson, And Dan Norman

The Tom Seaver trade was lopsided because it was never about baseball; it was about ideology. Tom believed that he deserved a big payday after Catfish Hunter got his 3.75 million deal with the Yankees. He thought, rightfully so, he deserved something similar. And he had a big fight with the Mets' top brass over that, and the crazy part is they actually settled it. They reached a deal, a 3-year extension at 300,000, which is very cheap for the Mets.

And then Dick Young published a column that had been leaked by the Mets brass that Seaver's wife Nancy was the one who was behind his demands because she was jealous of Ruth Ryan over making more. Seaver said, quote, "I called the Mets and told them that's it, it's all over, make the deal."

They mishandled that one so badly, losing out on the greatest man of all time. And what happened after that is the Mets entered their darkest era. And took them a decade to recover from that mistake.

6. Fernando Tatis Jr. for James Shields

The story of the Shields-Tatis trade at the time was all about Shields; no one knew who Tatis was. He was a 17-year-old who just signed a contract for $700,000, played rookie ball, and was the sweetener to take on a truly awful contract. The Shields contract was a four-year, 75 million deal the White Sox wanted out of; they ate 31 million of it. Shields posted an ERA of nearly seven for the rest of the season, and the White Sox collapsed. Tatis- we all know what happened with Tatis; he's the franchise cornerstone.

Sure, he's had his issues over the year, but he's a fantastic player, with some of his best years ahead of him. Now, to be fair, everyone seemed to pass on Tatis; he wasn't a prospect that people really believed in. It's not so much that the White Sox blew it, but nobody knew. San Diego had the scoop on him, and that's why they ended up winning it. It's an absolutely amazing, lopsided contract.

5. Jose Bautista From The Pirates to Blue Jays

Most of these other trades are about missing something in players and mis-evaluating who they were, but the Bautista trade is all about building a brand new player. You see, at that time, 27-year-old Bautista was just the utility guy who'd been around five different organizations and had even been claimed off waivers.

Pittsburgh, in return, got Robinson Diaz, not a catcher that anyone thought much of. This was a very minor trade, a footnote really, but Toronto's hitting coach managed to rework Bautista's swing timing. He got his leg kick started earlier so he could pull the ball. That led to that incredible 54 home run season in 2010, the 43 home run season in 2011, six All-Star selections, the famous bat flip.

This isn't really about the Pirates misjudging Bautista; they just didn't put in the effort to make him the player that he would become. It's very likely that if he hadn't gone specifically to Toronto, he never would have become the absolute monster that he was.

This is a great victory for Toronto for building him later. Did they see that he would become this player when they made the trade? I doubt it.

4. Rick Wise For Steve Carlton

A little bit like the Sieve trade, this one was a matter of principle. You had two teams that were in salary disputes. Steve Carlton and Rick Wise were both negotiating for better contracts. Carlton wanted 65,000 from the Cardinals and Busch refused to pay more than 60. That's just $5,000. Meanwhile Wise was holding out on the Phillies for about the same amount.

Both owners didn't want to surrender, they didn't want to give their guy what they asked for, so they would rather give the other guy what they asked for and withhold their honor. Now Wise was very good, throwing a no-hitter in 1971, he'd even hit two home runs in the same game. But there's just absolutely no comparison. Carlton went on to win four Cy Young's and be as dominant as we know that he was. Wise just continued to be dependable, didn't go on to throw any more no-hitters, wasn't quite as dominant. And all this was over $5,000. That's what cost Busch the four Cy Young's that he would have won and probably a lot more success for the team.

3. Orlando Cepeda For Ray Sadecki

Just hearing that you would trade Orlando Cepeda for Ray Sadecki tells its own story, but just like in the Foster trade, the Giants seem to have very good reasons to do that. They already had Willie McCovey at first base. Legend and Cepeda seem to have wrecked his knee, and he played only 33 games in 1965, and when he went to get his physical from the Cardinals, he presented the wrong knee to the doctor, hoping that he would pass.

And at that time, the medicine was much more primitive; the chances that he would actually recover from that injury seemed pretty negligible. But he certainly did recover; he won the 1967 MVP unanimously, only the second National League player to ever do that. Sadecki went 3.47 for the rest of the season. So it's understandable why, with a healthy McCovey and an injured Cepeda, they did what they did. But the end result was an absolute disaster for the Giants.

2. Nolan Arenado From The Rockies To Cardinals

The Arenado trade was particularly bad because not only did the Rockies send an incredible player to the Cardinals, but they also sent 50 million dollars along with him. This came because Nolan felt that he'd been disrespected by the front office, and he had gotten the payday that he wanted from the Rockies, but he also wanted them to spend so that the Rockies could compete, and he'd been promised to do that.

When that promise was broken, the front office had been very disrespectful to him, and he wanted to get out of Dodge. So a trade was organized, and the Rockies got Austin Gomber for prospects, and they sent 50 million to pay off his contract.

So they ended up getting much worse; the players didn't work out. Arenado kept winning Golden Gloves, and paying that much money for the privilege of getting considerably worse is a truly awful trade. And all they had to do was respect Arenado, and they didn't do it.

1. Harvey Kuenn For Rocky Colavito

The Colavito trade for Kuenn is particularly funny if you understand sabermetrics, OPS, all that stuff, because Colavito, who had just hit 42 home runs, was traded because the Indians believed that home runs were overrated and they wanted average instead. Kuenn had just won the batting title with .353, so the manager Frank Lane thought he was upgrading, and he made the trade two days before opening day.

Now, Colavito hit 45 home runs the next year; no one was surprised by that. But Kuenn only played one season in Cleveland, and they ended up trading him. One of the main reasons they traded him was that they had no power after trading Colavito.

So the next thing that happened was Cleveland didn't reach the postseason until 1995; that is what Indians fans called the Curse of Rocky Colavito. And who is the general manager on the other end of that deal? Bill DeWitt again, the same man who five years later would call Frank Robinson an old 30.

So we start and finish with Bill DeWitt, who leaves quite a legacy for some of the most lopsided trades in baseball history.

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