A couple of rules...
1) The trades are ranked by WAR differential. So to even make the list, you need at least a 30 WAR net difference.
2) Only actual TRADES are allowed. No SALES (so Babe Ruth and Eddie Collins are NOT on the list!)
3) I'm sticking mainly to OLDER trades. So many players these days are traded in the last year of their contract because the team already knows that they will not resign, and the resulting fire-sales are usually not expected to yield much anyway. So you really can't count those.
4) (Most important) To narrow down the search, each trade involves a Hall of Famer.
In January of 1923, the Red Sox acquired Norm McMillan, George Murray and Camp Skinner from the Yankees. McMillan gave Boston a servicible season around the infield, playing Short, Second and Third and hitting .253. No homers, but 42 RBI. Um... Did I say "serviceable?" Actually, he sucked: -1.1 WAR, which puts his performance at less than that of a minor league replacement. Murray didn't fair much better. Over two years, he would rack up a 9-20 record with a 5.48 ERA, netting -0.3 WAR. Skinner played the least, thus doing the least damage, hitting .231 over just 7 Games, netting -0.1 WAR.
So... Even if Boston got these three bums for FREE, they would still have been better off NOT making the trade.
And to think: all they had to give was a Left-Handed junk-baller named HERB PENNOCK. Pennock would pitch for 10 years in New York, garnering a 162-90 record, including a pair of 20-Win Seasons and a 19-6 performance in 1925 that topped the league in Winning Percentage. He would hurl 19 Shutouts, including 5 in 1928 to lead the league.
NET LOSS: 31.4 Wins over 10 years.
In December on 1920, the Red Sox would fill a hole at Second Base, acquiring Del Pratt from New York. (Yeah, there's a pattern forming.) Unlike the pocket-lint in the previous entry, Pratt actually performed well for Boston over the next two years, hitting .312 with 11 Homers and 188 RBI for 5.9 WAR. Not bad. They also got two better-than-average seasons out of Muddy Ruel at Catcher, hitting .266 with a homer and 73 RBI. Not great, but good enough to tack on 1 more WAR. The third part of the trade was also value-added as Hank Thormhalen gave the Sox 96.1 innings of a 4.48 ERA. This only amounted to a 1-7 record (for a terrible team, don't forget!) but it was good enough for 0.7 WAR. The only loser in the deal was Sammy Vick, whose .260-0-9 performance over 44 games COST them 0.4 WAR. But hey: All in all, they got SOME value, right?
Well, they did have to give up Harry Harper, whose 4-3 Record and 3.76 ERA was worth 0.9 WAR before he got hurt. Also in the mix was Mike McNally, a reserve infielder who hit .252 with 1 homer and 45 RBI over four years in new York off the bench. Nothing special, but worth 0.4 WAR. The bigger loss so far would be Catcher Wally Schang who manned the backstop for the next five years in New York to the tune of a .297 average, 5 Homer Runs and 213 RBI, for 9.6 WAR.
At this point, I should point out that the deal is ALREADY working out in New York's favor, but there was a FOURTH player involved: A Right Handed Pitcher named WAITE HOYT who, like Pennock, would pitch for 10 years in New York, tallying a 157-98 record and 3.48 ERA. Also like Pennock, he would notch a pair of 20-Win seasons, including a 22-7 performance in 1927 that led the league in both Wins and Winning Percentage. In 1928, in his second 20-win campaign, he also lead the league with 8 Saves! (WTF?!) Hoyt's decade-long performance was good for 32 WAR.
NET LOSS: 35.7 Wins over 10 years.
In December of 1948, the Washington Senators would make a deal to acquire All-Star Pitcher Joe Haynes from Cleveland. Haynes wouldn't work out so well in Washington, however, going 10-21 with a 5.42 ERA over the next four years. (-2.8 WAR.) Along for the ride was busted-up career relief pitcher Ed Klienman, who would put up an ERA of 18.00 in just 3 innings before they'd unload him on the White Sox. In just those three innings, he cost the the Senators -0.3 WAR. There was SOME value, however, in the form of First Baseman Eddie Robinson. For the next year and a half, he would hit .282 with 19 Homers and 91 RBI over 179 games before being also being traded to Chicago, though not with Kleinman. But this was good enough for 2.3 WAR, so not too bad, right?
Except that Washington GAVE UP First Baseman Mickey Vernon, who hit .245 with 18 Homers and 93 RBI over the next Year and a Half in Cleveland before being shipped out himself. Not as strong as Robinson with the bat perhaps, but it happened to be one the strongest defensive period of his career, and was worth a net 3.1 WAR overall. So... this trade was already in Cleveland's favor just considering the two First Basemen they swapped, plus the fact that they unloaded two less-than-minor-leaguers...
Oh yeah... AND acquired EARLY WYNN, who would go 163-100 with a 3.27 ERA over the next 10 years in Cleveland, including four 20-win campaigns. three All-Star appearances and an ERA title in 1950. Total value: 33.6 WAR.
NET LOSS: 37.4 Wins over 10 Years
To be fair with this one, it should be mentioned that when Connie Mack cleaned house in Philadelphia, he REALLY cleaned house. So in December of 1935 he agreed to take Minor Leaguer George Savino and Pitcher Gordon Rhodes from the Boston Red Sox. Savino never played a single game in the majors, which actually made him BETTER that Savino, who went 9-20 with a 5.74 ERA for the A's in 1936 before calling it a career after costing Philly -0.1 WAR.
For the privilege of taking these warm bodies off of the Red Sox's hands, they sent over Pitcher Johnny Marcum, who'd go 26-30 with a 4.68 ERA over the the next three years for Boston, netting 7.2 WAR. So this is a terrible, crap deal for Philly already.
But they also sent Boston their fear-inspiring, slugging First Baseman, THE BEAST: JIMMIE FOXX. Foxx would stick around for six and a half years in Boston en route to a .320 Average, 222 Home Runs and 788 RBI. In 1938, he'd take home the MVP Award, leading the league in Batting (.349), On-Base (.462), Slugging (.704), OPS (duh!), OPS+ (182), Total Bases (398), Walks (119) and RBI (175) (holy crap!). He'd also hit a club record 50 Home Runs that would stand until 2006. The following year, he'd win the Home Run Crown with 35, again leading the League in On-Base (.464), Slugging (.694), OPS (duh!) and OPS+ (188.) (He was the runner-up for the MVP that year.) He'd hit at least 35 Homer Runsin each of his first five years in Boston. For this awesome offensive performance this six-time All-Star (every full year in Beantown) would be credited with 33.2 WAR in Boston.
LOSERS: PHILADELPIA (A.L.)
NET LOSS: 40.5 Wins over 6+ Years
In December of 1971, the Angels were ready to trade their Shortstop Jim Fregosi. The Mets were interested, but his .233-5-43 performance in 146 over the next two years in New York was worth precisely 0.0 WAR. In other words: They have done just as well promoting their AAA Shortstop. But hey, at least they didn't give up all that much, right? I mean...
Frank Estrada would never play another game in the majors. And Don Rose went 1-4 with a 4.22 ERA out of the 'pen for Cali, costing them 0.7 WAR. Now Outfielder Leroy Stanton? That might have stung a little. He'd play the far corner for the next 5 years, hitting .247, with 47 Homers and 242 RBI, which was good for 4.2 WAR...
Oh yeah... AND the Mets through in a hard-throwing Righty with control problems named NOLAN RYAN. Ryan would go 138-121 over his eight years on the West Coast, with a 3.07 ERA and a pair of 20-Win Season to his credit. He'd also strikeout 200 or more batters in all but one of those years, topping 300 a then-record FIVE Times, including a single-season record 383 in 1973 that stands today. He'd also toss FOUR No-Hitters before leaving town for Houston in 1980.
LOSERS: NEW YORK (N.L.)
NET LOSS: 41.1 Wins over 8 years
In June of 1964, the Cubbies were looking for Pitching. So they jumped at their chance to acquire the one-time 20-Game winner, Ernie Broglio from the Cards. It didn't really work out for them though, as he'd go 7-19 with a 5.40 ERA over the next two and a half years in the Windy City, costing the Cubs 1.7 WAR. Another former 20-Game Winner in the deal, 7-Time Gold Glove Winner, Bobby Shantz, didn't fare much better: 0-1 with a 5.56, costing them 0.1 WAR before finishing the season in Philadelphia. They DID manage to get an Outfielder thrown in as well, Doug Clemens who would hit .223 with 3 Homer and 27 RBI over his year and a half on the team, costing them 0.2 WAR.
And although things didn't quite work out for the Cubs (when DO they?) at least they didn't lose much. Paul Toth never threw a pitch for St. Louis and Jack Spring gave them just 6 innings of 6.00 ERA ball before being unloaded on Cleveland, costing them 0.4 WAR in the process.
Oh, and uh... LOU BROCK spent the next Sixteen and a half years leading off for the Red-Birds, hitting .297, with 129 Homers, 814 RBI, and 1427 Runs Scored. He'd score over 100 runs six times, leading the League Twice. He'd also notch thee 200-Hit seasons (on his way to the 3000-Hit club) and lead the league in stolen bases eight times in nine years, setting a then-record (and still National League Record) with 118 in 1974, en route to setting the All-Time (and still National League) Career Stolen-Base record. The six-time All-Star would be worth 39.9 WAR to St. Louis.
LOSERS: CHICAGO (N.L.)
NET LOSS: 41.5 wins over 16 years.
Making the list for the third time is Boston. Who should simply not be allowed to deal with the Yankees at all, and who must have seen something special in Outfield Cedric Durst, who they acquired in May of 1930 from New York. Durst managed to hit .290 with 1 homer and 24 RBI for Boston before retiring, costing them 0.7 WAR.
And, as I said, they must have expected more, because for their trouble they gifted the Yankees with RED RUFFING, who'd go 231-124 with a 3.47 ERA over the next fourteen and a half seasons in the Big Apple. This would include four straight 20-Win Seasons, and 40 Shutouts, including a league-leading 5 in .1939. Total value: 41.7 WAR.
LOSERS: BOSTON (AGAIN)
NET LOSS: 42.4 Wins over 14+ years.
Remember how I mentioned that Connie Mack REALLY liked clean house when he got the inkling to? Well, in October of 1949, he agreed to take backup Catcher Joe Tipton from the White Sox. Tipton would give Philly a .243-12-48 performance over two and a half years before being shipped off to Cleveland. This performance, while hardly overwhelming, was good enough for a net-positive 1.7 WAR.
For this serviceable backup Catcher, the sent slick fielding Second Baseman NELLIE FOX to Chicago, where he would hit .291 with 35 Homers, 740 RBI and 1187 Runs Scored over the next Fourteen Years for the White Sox. He would take home three Golden Gloves, and the 1959 MVP Award, leading Chicago to it's first Division Championship since the 1919 Black Sox scandal. He'd rack up four 100+ Run Seasons, lead the league in Hits three times, including a 200-Hit season in 1954, and in triples, once, with 10 in 1960. This future Hall of Famer would be worth 44.5 WAR to Chicago.
LOSER: PHILADELPHIA (A.L.)
NET LOSS: 42.8 Wins over 14 Years
In December of 1981, San Diego was looking to fill the offensive hole they had at Shortstop, and placed their cross-hairs on a Switch Hitting Shortstop with a pair of 200-hit Season already under his belt in the form of Gary Templeton. And for the most part, Templeton worked out, hitting .252 with 43 Homers and 437 RBI over his nine and a half years for the Padres. Not super, but good for 8 WAR. And that wasn't all... In the deal they managed to snag Outfielder Sixto Lezcano, who hit .267 with 24 Homers and 133 RBI in 235 Games over a year and a half, before getting traded to the Phillies; good enough for 5.7 WAR in a very short time anyway! They also got Luis DeLeon, who managed to go 17-16 with a 3.06 ERA out of the pen (saving 31 games) over four years for San Diego. This was good for 2.7 WAR.
So San Diego's doing pretty good here, right? Three decent players, giving them16.4 WAR over 9+ years.
And it only cost them Al Olmstead, who never threw a pitch for St. Louis and Steve Mura, who went 17-27, with a 3.94 ERA over four years, good for just 0.2 WAR.
Oh... AND that offensive black hole of a Shortstop they were unhappy with: OZZIE SMITH. Who would wow St. Louis fans for the next fifteen years at Short, taking home eleven Golden Gloves, the 1984 ALCS MVP Award, making fourteen All-Star appearances and OUTHITTING Templeton, with a .262 Average, 27 Homers, 664 RBI and 991 Runs Scored. In the nine years that Templeton was in San Diego, Smith would net a higher OPS in all but ONE YEAR, and win the Golden Glove award at their shared position EVERY SINGLE YEAR.
LOSERS: SAN DIEGO
NET LOSS: 46.6 Wins over 15 Years
Connie Mack, cleaning house again (third time on the list.) He's benefit from the service of Second Baseman Rabbit Warstler for the two and a half seasons, following his acquisition from Boston in December of 1933. Warstler would hit .245 with 5 homer and 119 RBI over 321 Games in Philly, with a slick glove that netted him a whopping 2.3 WAR in that time. He also agreed to take on Bob Kline, but he wouldn't keep him long as he went 6-2, but with a 6.35 ERA (vulturing wins out of the bullpen, no doubt) and costing them 0.8 WAR before being air-mailed to Washington by season's end, where he'd finish out his career.
For this, Mack sent Tom Yawkey three players: Second Baseman Max Bishop, who [out]hit [Warstler] .251 with 2 Homer and 36 RBI over 157 Games in two years in Boston, good for 1.7 WAR; A once serviceable Lefty named Rube Walberg (what is with LHP's being named "Rube?") who once won 20 games, but who would spend most of his time in the bullpen in Boston, going 21-27, with a 4.44 ERA over four years in Boston before calling it a career. In Fenway in the 1930's however, this was good for 7.7 WAR.
At this point, it should be noted that Philadelphia is already underwater.
But they also threw in another left-handed Pitcher, ROBERT MOSES "LEFTY" GROVE. Grove would anchor the Boston Rotation for the next eight years en route to a 105-62 record, and his 300th win, with a 3.34 ERA. He'd manage only one more 20-win season in Boston, but pick up another FOUR ERA titles, bringing his career total to a record NINE. This five-time All-Star's hurling would be worth 42.5 WAR for Boston.
LOSERS: PHILADELPHIA (A.L.) (AGAIN)
NET LOSS: 50.4 Wins over 8 years
In February of 1972, the Cardinals picked up a Pitcher of real value: 17-Game Winner Rick Wise of Philadelphia. Wise would go 32-28 with a 3.24 ERA over two years in St. Louis, good for 7.2 WAR, before being traded to Boston in a deal to bring in All-Star Outfielder Reggie Smith. Not too bad, right?
Except that they gave up left handed Pitcher STEVE CARLTON, who would remain Philadelphia's ace for the next fourteen and a half seasons, going 241-161 with a 3.09 ERA, taking home a then-record (and still N.L. Record) FOUR Cy-Young Awards, notching a total of five 20-Win Seasons (after coming off another 20-win season in St. Louis!) and striking out 200 or more batter seven times, leading the league five times, including 310 in his 1972 campaign, where he was credited with 27 of the Phillies' 59 Wins that year. He'd also pick up 24 wins, with 3 more in the Post-Season, to help Philly to it's first ever World Championship in 1980. 60.5 WAR overall, if you're wondering.
LOSERS: ST. LOUIS
NET LOSS: 53.3 Wins over 14+ years
In April of 1916, the Boston Red Sox (again?!) would pick up Right Handed Pitcher "Sad" Sam Jones from Cleveland. Jones would go 64-59 with a 3.39 ERA over six years. This would include a 20-Win season in 1921 before being traded to New York (where he would put up another 20-win season two years later. Will Boston NEVER learn?!) Jones was a net-positive in Boston, howevre, with 9 WAR, as was infielder Fred Thomas, who would hit .257-1-11 in 44 games for Boston, for 0.8 WAR before being traded to the A's at season's end.
For this, they gave up TRIS SPEAKER who would would grace Center Field in Cleveland for the next eleven years, hitting .354 (holy crap!) with 73 Homers, 884 RBI and 1079 Runs Scored. This would include a Batting Title (.386) in his first year, also leading the league in On-Base (.420), Slugging (.502), OPS (duh!), OPS+ (186), Hits (211) and Doubles (41.) Doubles seemed to be his specialty, as he would to the league five more times, passing 50 in a season three times, en route to setting the all-time record. He would also lead the league in OBP two more times. He may have won more Batting titles as well, except... Ty Cobb. His total WAR? 71.
Oh, and how effed up is this...? Sad Sam Jones was traded to the Yankees in 1921, along with Bullet Joe Bush, who would also win 20 Games for New York, in 1922. (That's two 20-Game winners in two years, from the same trade!) And then New York would later trade Jones to the Browns for Cedric Durst... who, you may recall, the Bronx Bombers then traded to Boston to acquire RED RUFFING (above.) Boston REALLY should not be allowed to deal with the Yankees!
LOSERS: BOSTON (again, in more ways than one!)
NET LOSS: 61.2 Wins (in the Speaker trade alone) over 11 years
#1: the WORST trade of ALL-TIME...
In January of 1982, the Cubs and Phillies agreed to swap Shortstops. Philadelphia got the younger Ivan De Jesus, who hit .249 with 7 homer and 139 RBI over three years in Philly. Although he was their starter all three years, this underwhelming performance was worth a mere 2.2 wins.
Chicago, wouldn't fare much better, getting the
...Except that, to seal the deal, Philadelphia threw in a Second Base prosepct named RYNE SANDBERG, who would be turning double plays in Chicago for the next fifteen years (not including a year off for retirement in 1995). He'd hit .285 with 282 Homers, 1061 RBI, 1316 Runs Scored and 344 Stolen Basses for the Cubbies, who FINALLY managed to come out ahead of someone. He'd take home the 1984 National League's MVP Award, going .314-19-84, with 200 hits, whilst leading the league with 19 triples (!) and 114 Runs Scored, helping the Cubs to their first Division Championship in forty years. He'd add a Home Run crown to his resume in 1990, and lead the league in Runs two more times, topping 100 Runs Scored in a season Seven Times. He make ten All-Star appearances, win nine Golden Gloves and seven Silver Sluggers. His Hall of Fame career with the Cubs would be worth a whopping 65 WAR, making this the WORST TRADE IN HISTORY.
LOSERS: PHILADELPHIA (N.L.)
NET LOSS: 63.7 Wins over 15 Years.
For the record:
The Yankees pulled off three of the BEST trades of All-Time, netting them 109.5 Wins.
Cleveland pulled off two for a gain of 98.6 Wins.
The White Sox lone trade of note got them 42.8 Wins...
...Whilst California's got them 41.1.
St. Louis' two winners to one loser was still worth a positive 34.8 Wins.
The Cubs had one good trade and one bad one, to end up 22.2 Wins ahead of breaking even...
But the Phillies didn't fair as well: their 1-1 split record cost them 10.4 Wins.
The Senators made one big blunder that cost them 37.4 Wins...
...While the Mets' lone fumble lost them 41.1...
...and San Diego's 46.6.
Boston came out ahead twice, but behind four times, for a net loss of 79.8 Wins. (Curse of the Bambino? REALLY?!)
And Connie Mack's Philadelphia A's had three boners resulting in the loss of a whopping 133.7 Wins. (WHY is he in the Hall of Fame again?!)