Let’s make a steal

These are the most lopsided trades in baseball history

Getty Images

Over the years, there have been a million “What’s the worst trade in baseball history” stories, giving everyone a moment to relive the horrors of Brock for Broglio, Robinson for Pappas or a young player to be named for Bris Lord — the young player turning out to be a kid named Shoeless Joe Jackson.

A reader, Jack Bartram, writes in with a different idea. He believes the most lopsided trade in baseball history is not one of those more famous ones. He thinks it happened when the Houston Astros mostly washed-up slugger Glenn Davis to Baltimore for Steve Finley, Curt Schilling and Pete Harnisch. See, the three players Baltimore got compiled 141 Wins Above Replacement after the trade, while Davis managed less than one win. That is likely the biggest WAR difference in the history of deals.

Thing is: While that was obviously a horrendous deal for Baltimore — and I imagine Orioles fans of the 1990s have dreamed of life with Schilling as their ace and Finley in the outfield — it wasn’t necessarily a great trade for Houston. That’s because the Astros traded all three of those players away BEFORE they paid dividends. Combined, the three put up about 14 wins above replacement before being traded away.

So this led to an idea: For a trade to be lopsided, really lopsided, both teams should powerfully feel its impact. For instance, in 2004 New York Mets traded Australian minor leaguer Justin Huber to Kansas City for Jose Bautista. This was obviously a hugely lopsided deal — Huber played 72 uneventful big league games while Bautista became one of the best players in baseball.

But, I don’t really think it can count as a lopsided deal because Bautista never played even a single game in a Mets uniform. They traded him off in a package to Pittsburgh that brought along Kris Benson. And THAT can’t count as a lopsided deal either because Bautista played four lackluster years for the Pirates before Pittsburgh sent him to Toronto for Robinson Diaz.

And that, finally, WAS a lopsided trade:

Bautista in Toronto: 34.3 Wins Above Replacement.

Diaz in Pittsburgh: 0.6 Wins Above Replacement.

So, that’s a huge difference of 33.7 WAR. That places it in the Top 50 or so of best/worst deals in baseball history.

No, admittedly, this method of ranking trades has its limitations. Every method does. By simply calculating WAR, you can miss the context of trades. When the Braves traded Adam Wainwright and others to St. Louis for a one season of J.D. Drew, that was always was likely to be heavily tilted toward the Cardinals (there’s a 23-win difference now, and counting). But the Braves were thinking about a short-term drive toward a championship, and Drew played fantastic in his one season, leading the Braves to 96 wins and National League East title. So, simply counting WAR isn’t really a fair measure of that trade.

Also, sometimes these players bring return value in future trades. The Reds trading Paul Konerko to the White Sox for Mike Cameron was a huge WAR loss (23 wins difference to Chicago), but Cameron was a part of the deal that brought Ken Griffey Jr. home to Cincinnati.

Anyway, wall these complicating factors aside, this is still a pretty fun way to determine the most lopsided trades in baseball history.  Let’s start with a few honorable mentions:

Phillies trade Ferguson Jenkins and Adolfo Phillips to Cubs for Bob Buhl and Larry Jackson

Difference: 46 WAR.

So much is made of the Cubs sending Lou Brock to the Cardinals for Ernie Broglio — perhaps the most famous bad/good trade in baseball history — that this one usually gets overlooked. But in truth, this was an even more one-sided trade than Brock for Broglio, which had a 41.9 WAR difference.

Mets trade Amos Otis and Bob Johnson to Kansas City for Joe Foy

Difference: 47 WAR

The Kansas City Royals made a series of amazing trades in the early 1970s — for Fred Patek, John Mayberry and Hal McRae among others — and this was the best one. Otis became the first real star in Royals history.

Padres trade Ozzie Smith to St. Louis for Garry Templeton, Sixto Lezcano and Luis Deleon

Difference: 47 WAR

At the time, it was viewed as a swap of perhaps the two most exciting young shortstops in baseball. Templeton was a sensational young hitter; Ozzie Smith couldn’t hit. Numerous analysts of the time thought the Padres got the better of the deal.

December 10, 1991: Astros send Kenny Lofton to Cleveland for Eddie Taubensee

Difference: 50 WAR

Many scouts just never believed Lofton would hit. As it turned out, he had a near-Hall of Fame career.

Red Sox trade Babe Ruth to Yankees for cash

Difference: 143 WAR

I list this because it’s famous but it’s not really a trade. There were no other players involved. The Red Sox got $100,000, the Yankees got 142.7 wins above replacement. That adds up to $700.77 per win. To be fair: $700.77 was worth more in those days.

And now, here we go, the ten most uneven trades in baseball history:

10. April 12, 1960: Indians trade Norm Cash to Detroit for Steve Demeter

Difference: 52 WAR

In Cleveland, we grew up on the dark mythology of the Rocky Colavito trade. On April 17, 1960,  Cleveland general manager Frank Lane created a national stir when he traded home run champion and local hero Rocky Colavito to Detroit for batting champion Harvey Kuenn.

The idea of a home run champ for a batting champ was exciting at the time when those were the two biggest statistics in baseball. But, the trade was viewed as disastrous in Cleveland right from the start. First of all, Cleveland loved Colavito. The day it happened the Cleveland Press reported fans calling in 10-to-1 against the deal.

Second of all, even in those days when batting average was king, there was a general understanding that a low average power hitter like Colavito had more value than a high average singles hitter like Kuenn. As New York’s Elston Howard said, “How can they give away a guy who hits 42 homers and knocks in 111 runs even for someone like Kuenn?”

Third, Colavito was younger than Kuenn. True, it was only about three years but they were the RIGHT three years — Colavito was 26 and entering his prime when he went to Detroit, Kuenn was 29 and coming out of his when he got to Cleveland. That trade was, as has often been repeated, a disaster. Pal Terry Pluto wrote a book called “The Curse of Rocky Colavito.”

And so it was easy to miss that five days earlier, Lane made an EVEN WORSE trade — made one of the worst trades in baseball history.

Norm Cash never played a single game for Cleveland. The previous December, he had come to Cleveland in another weird Lane deal — Lane had traded Minnie Minoso back to Chicago in a sprawling 11-player deal that did not seem to be about anything in particular. Cash was one of the anonymous players in the deal, a guy both teams saw as a utility player at best. It’s not entirely clear why those two teams could not see Cash’s potential, but Detroit general manager Rick Ferrell certainly did. When Lane called him, Ferrell said, he was so shocked that he assumed the Indians were offering “cold cash,” not “Norm Cash” in a trade. When he realized it was Norm, he jumped at the deal.

In his first year with Detroit, Cash hit .286/.401/.501 with 18 home runs. The next year, he had what many consider to be one of the great fluke years in baseball history — hit hit .361/.487/.662 with 41 homers, 132 RBIs, a league leading 193 hits and 9.2 WAR.

It WAS fluky — Cash later admitted he had corked his bat that year — but he had a very, very good career in Detroit, hitting 30 or more homers four other times and creating more than 1,200 runs in a very low-scoring environment.

Cleveland, meanwhile, received Steve Demeter, who got five at-bats for the Indians. He did not get a hit in any of them. He did hit 272 career homers in Rochester. In Cleveland, they will always call it The Curse of Rocky Colavito, but the Cash trade was even worse.

* * *

9. February 25, 1972: Cardinals trade Steve Carlton to Philadelphia for Rick Wise.

Difference: 57 WAR.

So in early 1972, Carlton and Wise were both unhappy and unsigned when the two general managers got the bright idea of swapping problems. It did not seem unreasonable at the time. Carlton and Wise were about the same age (Carlton is nine months older) and they’d had somewhat comparable success:

Wise: 178 starts, 75-76, 3.60 ERA, 3.09 FIP, 717 Ks, 327 walks.

Carlton: 172 starts, 77-62, 3.10 ERA, 3.02 FIP, 951 Ks, 449 walks.

Wise felt like the differences in the numbers between him and Carlton were an illusion: “I’ve been tagged a .500 pitcher,” he said, “but every year our team managed to end up 30-40 games under .500, so I don’t think that’s a true evaluation or is indicative or how I can pitch. Although my record hasn’t been as impressive as his the last couple of years, I think I’m the same caliber pitcher he is.”

Many people agreed with him. In Philadelphia, one columnist wrote that the deal — in part because Wise was also a terrific hitter who banged six home runs the year before — made the Phillies come out second-best.

Of course, they were all wrong. Carlton went on to have one of the greatest pitching seasons in baseball history for Philadelphia in 1972, and he proved the stubborn and indomitable ace of a Phillies team that won a World Series and contended throughout. He won four Cy Young Awards. Wise pitched fairly well for a couple of years in St. Louis and was traded to Boston for Reggie Smith.

* * *

8. March 30, 1992: White Sox trade Sammy Sosa to the Cubs for George Bell.

Difference: 59 WAR.

General managers used to bow at the altar of RBIs. It’s possible that some still do — you will hear some talk about needing “run producers” — but it used to be a plague. Why in the world would a baseball team trade a promising 23-year-old outfielder for a 32-year-old George Bell? Well, the answer is in the RBIs. In Bell’s first year with the White Sox, he hit 25 homers and drove in 112 RBIs.

True, he also had a .294 on-base percentage, a .418 slugging percentage and was disastrous in the outfield. True, in context, Bell had a dreadful season even with those RBIs. But, hey, the White Sox wanted a run producer. And they got one.

Of course, they did not envision Sosa bulking up and becoming the only hitter in baseball history to slam 60-plus homers three times — even now, that’s hard to imagine — but a doddering George Bell? Really? Just for the RBIs?

* * *

7. August 12, 1987. Tigers trade John Smoltz to the Braves for Doyle Alexander.

Difference: 61 WAR.

This is one of those “you had to be there” trades. The day before Doyle Alexander made his first start for Detroit, the Tigers were in second place, a game and a half behind the Blue Jays. Their rotation was a mishmash of veterans and their bullpen was in shambles, but their lineup was powerful and leading the league in runs. It was a lot like the Toronto Blue Jays this year. The Tigers just needed a pitcher to bring everything together. Doyle Alexander turned out to be the man for the moment.

He made 11 starts in the last six weeks of the season. The Tigers won all 11. During the stretch, Alexander only gave up three runs or more three times, and he never gave up more than four — every time out he gave that good offense a chance to win. And they won every time.

It’s not often that one person can make a difference in a pennant race, but consider this: Over those final 49 games, the Tigers went 21-17 in the games that Alexander DID NOT start . They, of course, went 11-0 in the games that he did start. They won the East by two games. So, you would have to say, that the Tigers got EXACTLY what they wanted out of that deal.

Well, OK, not exactly what they wanted. It turned out that Alexander was an absolute fiasco in the championship series — he started twice against the Twins, gave up six runs (and two Gary Gaetti bombs) in the first game, then came back in the decisive game and got pulled in the second inning after giving up six hits and four runs. The fates giveth and the fates taketh away.

And when it all ended, the smoke cleared and … yep, the Tigers had given up future Hall of Fame John Smoltz. Was it worth it? This is a viable question because the Kansas City Royals just gave up three prospects — one of them talented lefty Brandon Finnegan — to Cincinnati for Johnny Cueto in the stretch run. You can say: Well, Finnegan isn’t going to the Hall of Fame. But at the time of the Alexander deal, John Smoltz was a no-control Class AA pitcher with a 5.68 ERA.

Is it worth the deal? I think the Tigers — and the Royals — make such deals with their eyes open. You don’t get many chances to take a hard run at the World Series. If the Royals win the World Series, I suspect they will determine it was worth the deal no matter what Finnegan and the others do. If they flop in the playoffs the way the Tigers did, well, that’s a whole other story.

* * *

6. April 9, 1916: Red Sox trade Tris Speaker to the Indians for Sad Sam Jones and Fred Thomas.

Difference: 63 WAR.

The main piece of this deal was the $55,000 that Cleveland sent over in the deal. This was a precursor to the Ruth sale a couple of years later.

It was made almost exactly 100 years ago, but if you listen to the Red Sox manager Bill Carrigan, I imagine you hear echoes of today:

“It’s a matter of business,” Carrigan said. “And anyone who figures baseball is not a business does not know the game. Speaker has done and all that’s left for us is to keep our heads up and to do the best we can.”

The Red Sox did OK without Speaker, winning 90-plus games the next two years and winning the World Series in 1918. Well hey, you can win a lot of games when Babe Ruth is dominating as a pitcher AND leading the league in home runs.

Speaker was fantastic in Cleveland, but it wasn’t until 1920 that the Indians finally won a championship.

My favorite quote from this trade came from a somewhat obscure outfielder name Clarence Walker, who people kept calling Tillie (sometime spelled “Tilly”). Walker had become a minor celebrity when he showed up in 1914, hit well, and displayed an outfield arm that many would call the greatest they ever saw. He then went through the rigors of Deadball baseball, getting released, getting cheated and so on. He ended up in Kansas City. He wasn’t crazy about that. “If they had been a major league in Hades,” he said, “I would have jumped before I went to Kansas City.”

Anyway, Walker turned out to be the guy who “replaced” Speaker in Boston. On the day after the trade, there was a headline in the Boston Daily Globe: “Walker Will Do His Best.” The subhead: “Can’t Fill Speaker’s Shoes, He Says.”

“I am tickled to deal to come to Boston,” Walker said. “But please make it plain to Boston fans that I am do not expect to fill Speaker’s shoes. I am not so good as Speaker.”

* * *

5. January 27, 1982: Phillies trade Ryne Sandberg and Larry Bowa to the Cubs for Ivan DeJesus.

Difference: 66 WAR

While the Cubs are famous for being, well, the Cubs, in truth they have been on the winning side of some of baseball’s most spectacularly unbalanced deals. As mentioned, they got Fergie Jenkins in a steal and they got Sammy Sosa in another. They got Derrek Lee for Hee-Seop Choi and pilfered Aramis Ramirez from Pittsburgh for Jose Hernandez and Bobby Hill.

The Sandberg deal, though, was something else, a Philadelphia miscalculation of epic proportions. Sandberg had shown promise in the minor leagues; he flashed a bit of power with quite a bit of speed. He was a somewhat erratic shortstop, but he was so athletic that when the Phillies moved him to second base he seemed at ease. The Phillies had 31-year-old Manny Trillio there at second; it’s hard to see just how they expected that to last.

But one thing general managers can do — especially, it seems, in Philadelphia — is believe that the present will last forever. When the Phillies traded Sandberg, they said (based on the way Philadelphia writers wrote about the deal) that he would likely never become more than a utility infielder.

Cubs fans apparently hated this deal at first. They liked DeJesus and believed that giving him to the hated Phillies was like giving Philadelphia another pennant. Looking back, it’s hard to find anyone who had anything good to say about Sandberg. Even the Chicago Daily Herald, who halfheartedly defended the deal, admitted that Sandberg might “never have a prime.”

It’s hard to imagine how a 22-year-old middle infielder with power and speed could be so lightly regarded. If that exact trade as made in 2015, ESPN’s Keith Law and others would be SAVAGING the Phillies for the move. But baseball was a little bit different then.

* * *

4. November 29, 1971: Astros trade Joe Morgan, Jack Billingham, Cesar Geronimo, Ed Armbrister and Denis Menke to Reds for Tommy Helms and Lee May.

Difference: 66 WAR

Here was another trade where the winning team’s fans were initially disgusted. Reds fans were furious that general manager Bob Howsam had traded away Lee May, who led the 1971 Reds in home runs (39) and RBIs (98). The trade made absolutely no sense to most Cincinnati fans, especially because the key player returning was a 27-year-old second baseman who hit .256, .268 and .236 the previous three seasons.

People didn’t know just how good a player Joe Morgan already was, and they sure as heck didn’t know that he was about to emerge as the best player in the game. There were numerous things obscuring Morgan’s genius for the game.

— He played in a terrible hitters park, which sapped his power and deflated his batting average by probably 20 to 30 points. In 1971, for instance:

Home: .220/.332/.354 with four homers, 18 RBIs, 34 runs and 16 stolen bases.

Road: .286/.366/.451 with 9 homers, 38 RBIs, 53 runs and 24 stolen bases.

So if you doubled his road numbers, you had a second baseman hitting .286 with 18 homers, stealing 48 bases, driving in 76 runs and scoring 106.

In 1972, Morgan hit .292 with 16 homers, stole 56 bases, drove in 73 runs and scored a league-leading 122 runs.

— He walked a ton, and few appreciated the value of walks then.

— He was a proud and deeply motivated player who had to deal with a lot of incompetence and racial tension with the Astros.

Morgan DID improve in Cincinnati. He always credited Pete Rose for teaching him how to become a winning ballplayer. But, in all the important ways, Joe Morgan already WAS a winning ballplayer at the time of the trade. This was something Bob Howsam saw and the Astros and many fans missed.

* * *

3. July 18, 1939: Boston trades Pee Wee Reese to Brooklyn for Red Evans, Art Parks and $35,000.

Difference: 66 WAR

We talked about how the Cubs, despite their reputation, have actually been on the winning end of some of the most uneven deals in baseball history. The bizarro version of that is the Red Sox, who have made many of the worst trades ever. They sold Babe Ruth, of course. They traded away Tris Speaker. They traded away the young Curt Schilling. They also have the No. 2 worst trade ever, which is coming up.

And they traded away the young Pee Wee Reese. The Red Sox liked Reese a lot; the legend they bought the Louisville club just to get him probably isn’t entirely true, but they certainly knew that Reese was a good young player. So why did they trade him? Well, that answer is not entirely clear, but it seems to come down to Red Sox manager and shortstop Joe Cronin and Red Sox owner Tom Yawkey.

Cronin had been baseball’s best shortstop in the early 1930s, and in 1938 at age 31 he was healthy again and he had a renaissance season, hitting .325, walking 91 times, leading the league with 51 doubles and finishing seventh in the MVP balloting. Cronin was convinced that he had at least five more good years left (he did have three good years left) and because he was the manager as well as shortstop, his views were taken seriously. He also had his doubts about Reese; Cronin believed him too small to be an effective every day player.

Cronin had Yawkey’s ear and so Reese was traded for irrelevant minor leaguers and some cash.

“Reese is a most promising prospect and should develop into a major league star with another year or two of experience,” Dodgers president Larry McPhail was quoted saying after the trade was made.  Reese stepped in a dazzling defensive shortstop right away though his bat did not come around until after he got back from World War II. By then, to be fair, the Red Sox had Johnny Pesky at shortstop, and he was a fine player, though not quite Pee Wee Reese.

* * *

2. August 30, 1990: Red Sox trade Jeff Bagwell to Astros for Larry Andersen.

Difference: 78 WAR.

Of all the trades on this list, the one that makes the least sense to me is the Bagwell for Andersen deal. I just cannot quite figure how the Red Sox would take a gifted right-handed hitter BORN in Boston, RAISED in New England, and trade him for a 37-year-old reliever heading to his sixth team. I doubt there is anything that could ever explain this one well enough.

“Larry is a veteran major-league reliever who should bolster our bullpen for the stretch run,” Red Sox GM Lou Gorman said at the time. “Although the price was high, we are happy to have acquired a pitcher with postseason experience.”

Inexplicable. Utterly inexplicable. Sure, there has been some conjecture that Boston was worried that Bagwell did not have a position. He was playing third at the time, and the Red Sox did not think he could stick there (the Red Sox also seemed to think Tim Naehring was a better third base prospect).

Gorman has said and written that Bagwell’s path to first base was blocked by Mo Vaughn, but this seems a blurry retrospective. Vaughn and Bagwell are almost the same age and Bagwell was clearly more advanced than Vaughn. He won the 1991 Rookie of the Year while Vaughn spent much of that season (and the next) in Class AAA.

There also has been some conjecture that Boston worried that Bagwell’s power would never come around. But this too is silly; he was leading the Eastern League in hitting when the trade was made, he was hitting a lot of doubles, and he was only 22. He hit 15 homers in his rookie year, despite playing half his games in the Astrodome, and 18 the next, 20 the next, then 39 in the 1994 strike season. No scout worth hiring could have missed his power potential.

The answer to the Bagwell conundrum, frankly, is incompetence on a sort of grand scale. It happens. People have blind spots. Opinions congeal with the force of repetition. Somewhere along the way, the Red Sox decided that Bagwell just could not play — and the team fell for the “We really need a veteran reliever for the postseason” nonsense.

Even based on that absurd line of reasoning, the deal was a failure. Andersen appeared in three games in the ALCS. In Game 1, he came in with a 1-0 lead, walked the leadoff hitter, gave up a single and the sac fly that tied the game. In the next inning, he gave up a leadoff single in what turned out to be the winning run. In Game 2, he came into a game with his team down by a run and pitched a bumpy but scoreless inning.  In Game 4, the last game, he came in with his team trailing 3-0 and pitched another bumpy but scoreless inning.

Then he left for free agency.

For that, the Red Sox gave up one of the best first basemen in the history of the game, and probably the greatest player ever born in Boston. So, so weird.

* * *

1. December 15, 1900: Cincinnati Reds trade Christy Mathewson to the Giants for Amos Rusie.

Difference: 95 WAR.

Here is a story that appeared in the Sports and Sportsmen section of the Lowell Sun on Dec. 27, 1900, just when the legendary new York Giants pitcher Amos Rusie was deciding whether or not to accept the trade to Cincinnati. It is filled with all the misogyny and absurdity of the time:

Amos Rusie, one of the best baseball pitchers that ever curved a ball over the plate, is writing a book these days on the great national game. He is living in seclusion in a suburb of Muncie, Ind., and has given up bad habits at the request of his wife. It is said Mrs. Rusie made this a condition before remarrying Amos after their divorce last spring.

It was said that Mrs. Rusie exacted a promise from Amos that he would never again visit New York City and particularly not the neighborhood of One Hundred and Twenty-fifth street. He also was required to promise that he would never again play baseball except as recreation with his fellow townsmen of Muncie and environs.

All this Rusie agreed to, and also in future to avoid bad whisky, indulgence in which had frequently caused the big pitcher to imagine his wife was a League ball.  These hallucinations are said to have led Amos to attempt to not only hurl Mrs. Rusie over the home plate, but also convert her into an outshoot, with a second story window as the objective point.

But now all this is changed. Although nobody in New York ever suspected Rusie of possessing literary ability, he is said to have buried himself in obscurity for the purpose of writing a book of his knowledge of baseball and relating his reminiscences of the game. Rusie has been offered many opportunities to write about the game and the players, but according to the report, “he desires to tell all he knows that is interesting within the covers of his own book.

Well, yeah, that’s, um, interesting.Rusie really was a larger than life figure in 1900, even though he had not pitched for two years. They called him the Hoosier Thunderbolt. And that year, the Reds came up with a scheme to get Rusie to pitch for them. The Giants had signed Christy Mathewson just out of college, and he had struggled at first so they shipped him off to get some seasoning. But by doing so, they exposed him to the Rule 5 draft. This gave the Reds a chance of a lifetime — they plopped down the $100 fee and drafted him. It could have been the greatest $100 deal in baseball history. Mathewson is one of a handful of pitchers in the discussion for greatest ever.

But, all along, it was just a ploy: Apparently the Reds had no interest in spending the money necessary to sign Mathewson. Instead, they used Mathewson in a trade for the rights to Amos Rusie. They were dreaming of giant crowds.

Rusie did try to pitch for the Reds — he pitched three games. It was no good. He allowed 43 hits and 25 runs in 22 innings. He then disappeared into retirement with his wife, who stayed with him until his death. Rusie was a titan of the game in the nineteenth century, but in the end he was remembered — if at all — as the footnote who was traded for Christy Mathewson. Thirty-five years after he died, Rusie was elected to the Baseball Hall of Fame.