MLB Trades: Ranking the 50 Biggest Trades Ever

Matt TruebloodSenior Analyst IJanuary 4, 2012

MLB Trades: Ranking the 50 Biggest Trades Ever

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    Trading for a player like Roy Halladay is not a value-based maneuver; it is a statement.

    The Philadelphia Phillies had lost the 2009 World Series to the New York Yankees. When they managed to package several top prospects and land Halladay from the Toronto Blue Jays that winter, they made it clear that they would not accept less than elite status in the National League for the long-term.

    Halladay isn't the only example of this phenomenon, of course. High-profile trades happen every year, and some of them can alter the direction of the franchises involved. They're exciting for fans of any team, because they represent a bold wager:

    "Here's our superstar," says Team A. "We feel we're better off with your top three prospects."

    "Maybe you will be," replies Team B. "But we're going to win titles with your erstwhile stud at the front of our rotation, or in the middle of our lineup."

    That's exhilarating. It's fun to watch teams challenge each other. It's also fun, of course, when it blows up in one team's face.

    Here are the 50 biggest trades in MLB history, based on the reaction to the deal at the time. No Lou Brock or Jeff Bagwell here, as those were under-the-radar moves that surprised everyone when they turned out to be mega-deals.

50. Bill Buckner to Chicago Cubs, Rick Monday to LA Dodgers

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    In January 1977, the Chicago Cubs were in the midst of a total rebuild. They had some talented pieces remaining from a series of contending clubs in the late 1960s and early 1970s, but they had struggled to stay relevant the previous three years.

    Therefore, when they got a chance to add two promising young players at the cost of incumbent center fielder Rick Monday, the Cubs pounced. From excess depth, the Los Angeles Dodgers produced Bill Buckner and Ivan De Jesus, two of the team's coveted youngsters.

    Monday constituted a fine catch at the time, coming off a 32-homer season in which he also played solid defense in center field. Moves like these fail to get remembered because they lack transcendentally great players, but in 1977, this deal got a good deal of attention.

49. Bill Buckner to Boston Red Sox, Dennis Eckersley to Chicago Cubs

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    If Buckner was a relatively unproven young player when packaged up and sent to Chicago in 1977, by 1984, he was a bona fide first baseman of whom many thought very highly. He won a batting title in 1979, and was a 1980 NL All-Star. He played solid defense at first base, too.

    The Cubs, though, no longer needed Buckner. The arrival of slugging prospect Leon Durham made Buckner expendable, and expend him the team did. They sent Buckner to Boston for Dennis Eckersley and Mike Brumley.

    Eckersley won 20 games in 1980, but by the time the Sox dealt him to Chicago, he had posted a season-plus of 5.00-ERA baseball. It was getting ugly. The trade came in May, and worked out well for the Cubs in the short term: Eckersley pitched to a 3.06 ERA in 330 innings for them in 1984-85, helping them to a playoff berth in 1984.

    By 1986, though, it was Buckner who reached the World Series with his new team, so who got the last laugh?

48. Ray Sadecki to St. Louis Cardinals, Joe Torre to New York Mets

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    Ray Sadecki had a very solid big-league career. He pitched 2,500 innings plus one out, won more games (135) than he lost (131), and posted a sturdy 3.78 career ERA.

    After the 1974 season, though, Sadecki found it hard to stay in one place for long. Over his final three seasons, he was traded three times and released three times. The first of those late-phase trades was to his original team, the St. Louis Cardinals, in exchange for catcher Joe Torre. For reasons soon to be made clear, this was great fun for many baseball fans.

47. Orlando Cepeda to Atlanta Braves, Joe Torre to St. Louis Cardinals

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    On St. Patrick's Day 1969, Joe Torre had first joined the Cardinals. After playing star-level baseball for the Braves for years, he was starting to slip, and the Braves jumped at a chance to deal a man whose OPS had dropped from .943 to .790 to .709 in three seasons.

    They got in return Orlando Cepeda, 1967 NL MVP and established star slugger. Cepeda, too, had seen his production drop, but the consensus at the time was that the Braves had won that deal. They had gotten the better of two dimming former superstars.

    Not so. Torre won an MVP award of his own for St. Louis, in 1971, before being dealt away in 1974.

46. Ray Sadecki to San Francisco Giants, Orlando Cepeda to St. Louis Cardinals

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    Hey, it all comes together! As you can now see, in 1966, the Giants dealt Cepeda for Sadecki. In 1969, Cepeda was traded for Torre, and in 1974, it was Torre for Sadecki, to close the circuit. All the while, all three players provided underrated stellar performances to their clubs, and each time a trade happened, it caught the public eye.

45. Sammy Sosa to Baltimore Orioles, Jerry Hairston, Jr. to Chicago Cubs

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    In a painfully protracted melodrama, the Chicago Cubs and Sammy Sosa parted on unhappy terms after the 2004 season. Sosa behaved childishly after the team was eliminated from playoff contention during the season's final weekend, and management seemingly took his cues.

    When the dust settled, the Cubs had a hard time finding a home for a recently-subpoenaed past-prime slugger with back problems. They got Jerry Hairston, Jr., Mike Fontenot and a bit more, but ultimately, the trade was news mostly for the bitter circumstances—and the colorful media circus tent—under which it occurred.

44. Ken Boyer, Art Ditmar and Bobby Shantz to New York Yankees from Kansas City

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    Here is one of the more blatant examples of a common 1950s and 1960s phenomenon: The New York Yankees used the Kansas City Athletics as a farm team.

    The Yankees thoroughly and cruelly dominated MLB in those days, and one of their chief mechanisms for doing so was to keep an extra stable of players within their reach.

    The Athletics were owned by a close friend of Yankees owner Dan Topping at the time, and an obliging friend it was: Topping used the A's to skirt MLB rules about guaranteed roster spots and to double the Yankees' flexibility when it came to shuttling and acquiring players.

    This particular deal was one of the largest ever. It included 12 players in all, a straight-up six-for-six, but all three of the impact players involved went to New York. Everyone knew it. In fact, Clete Boyer had essentially been a Yankee all along.

    Because of league rules at the time, players who received a substantial amateur bonus were guaranteed an MLB roster spot for the first two years of their time. The Yankees could not be bothered by such things, so the A's signed Boyer on New York's orders, and held him in incubation until such time as his clock ran out. 

    Ditmar, Shantz and Boyer were key members of great pennant-winning teams as late as 1964. It's not hard to argue that without this deal and some six or seven others similar, the Second Yankee Dynasty would have flamed out a decade earlier.

43. Dan Haren to Arizona Diamondbacks, Carlos Gonzalez to Oakland A's

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    The payroll constraints under which Billy Beane continues to operate in Oakland seem to get more pernicious by the day. This winter, he is voluntarily selling off a huge chunk of his roster in the hope of being ready to compete more seriously by the time Oakland can open a new stadium in San Jose years from now.

    In 2007, the victim was Dan Haren. Beane had gotten Haren in the Mark Mulder sell-off swap with St. Louis three years before, but no longer wanted the hassle of Haren's impending arbitration salaries. He got in return a solid cluster of prospects, the headliner of which was ultra-athletic outfielder Carlos Gonzalez.

42. Matt Holliday to Oakland Athletics, Carlos Gonzalez to Colorado Rockies

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    Gonzalez was a top-30 prospect in all of baseball when Beane acquired him, but he was largely a tools guy. In one season in the Oakland organization, Gonzalez got a half-season of MLB exposure, found a lot of holes in his own game, and fell in the estimation of many out of elite young player status.

    It's hard to say if that was what drove Beane to deal Gonzalez. It might well have been. He may have hoped to flip Matt Holliday—who was certainly the story-topper of the trade—for enough to justify letting go of Gonzalez. He didn't, and this became the most well-publicized of Beane's latter-day failures after the flurry of success he had pre-Moneyball.

41. Rick Sutcliffe to Chicago Cubs, Joe Carter and Mel Hall to Cleveland Indians

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    Give the Cubs credit; they saw an opportunity in 1984, and gave themselves every chance to seize it. With the emergence of Ryan Sandberg as a superstar and a solid core around him, the team began building its starting rotation by trading excess veterans and simply plugging in young positional guys. 

    The Buckner-for-Eckersley deal is a less-remembered such move. This trade does not get forgotten very often.

    Sutcliffe was a potential ace; everyone knew that. He had won the NL Rookie of the Year award in 1979, and had won 31 games for Cleveland in 1982-83. Still, when the Cubs snagged him, he found a new gear. Sutcliffe pitched to a 16-1 record in Cubs blue. 

    Carter, meanwhile, was a promising rookie with slugging potential, and he would find his way into baseball annals more than once in his career.

40. Robin Ventura to New York Yankees, David Justice to Mets

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    Barely more than a year after meeting in the 2000 World Series, the Yankees and Mets both felt their rosters had become bloated. Both felt their clubhouses were too divided and too entrenched. Therefore, since each also had changing positional needs, they made a very notable swap of two great all-around athletes with two very different clubhouse personas.

    The Mets would flip Justice before he played a game in their uniform, but Ventura cranked 27 home runs for the 2002 Yankees.

39. Brian Giles to Padres, Oliver Perez, Jason Bay to Pittsburgh Pirates

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    As August trades go, this one was a coup. The Padres got a terrific middle-of-the-order bat in Giles, but gave up two prodigiously talented young players to do it. It was an odd choice, not least because when the deal went down (August 26, 2003), both teams were far from contention. 

    It worked out well for both sides, as Giles and Bay had roughly equivalent value over the next few years, and Perez struggled to find consistency after an excellent 2004.

38. Bert Blyleven, Al Oliver and the Joy of the Winter Meetings

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    In December of 1977, a delightful trade happened. It was truly awesome, a blast for all involved. Here's the quick rundown:

    Pittsburgh Pirates send:

    Atlanta Braves send:

    • Willie Montanez to the New York Mets

    New York Mets send:

    • Jon Matlack to the Texas Rangers
    • John Milner to the Pittsburgh Pirates

    Texas Rangers send:

    • Tommy Boggs, Adrian Devine and Eddie Miller to the Atlanta Braves
    • Tom Grieve and Ken Henderson to the New York Mets 
    • Bert Blyleven to the Pittsburgh Pirates

    That's the sort of deal that can only happen at the Winter Meetings.

    It began with the Mets and Rangers discussing Milner, who didn't even end up on the Rangers.

    After some haggling between those two clubs (Ted Turner, the then-owner of the Braves) walked by and plopped himself into the picture. Soon, the Pirates entered the negotiation by offering up Oliver—the bat Texas had craved from the start—and came away with perhaps the biggest prize in the deal, Blyleven, who would help lead them to the 1979 World Series title.

37. Keith Hernandez to New York Mets, Neil Allen to St. Louis Cardinals

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    It's possible Keith Hernandez is the only player who ever truly changed games on a regular basis with his defense at first base. He was special. It's not clear what made his long-time team, the one for whom he had already won an MVP award, forget that at the 1983 trade deadline, but that's what happened.

    The St. Louis Cardinals felt they needed to go in another direction, so they dealt Hernandez and moved on. It's hard to knock the strategy, since St. Louis actually reached the World Series one year sooner after this trade than did the Mets, but there's no doubt the deal made the Mets more complete and more viable as NL competitors overnight.

36. Ferguson Jenkins to Texas Rangers, Bill Madlock to Chicago Cubs

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    Absurd as it seems in hindsight, it's possible the Cubs thought Jenkins was washed-up already when they dealt him to Texas in late 1973.

    That season, Jenkins had fallen short of 280 innings for the first time since 1966; watched his ERA balloon to a career-worst 3.89; allowed a career-high 35 home runs; and finished just seven starts, after six straight seasons with at least 20 complete games.

    If they thought that, they were wrong, but they had the good sense to get one of the most coveted young hitters in baseball in the deal just in case. Bill Madlock won two batting titles and hit .336/.397/.475 in his three seasons with Chicago.

35. Josh Beckett, Mike Lowell to Boston Red Sox, Hanley Ramirez to Florida

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    The Marlins got a true star in Ramirez and a very nice complementary piece in Anibal Sanchez in this trade, so it doesn't qualify as a Marlins fire-sale special. Still, the two veterans they dealt to the Red Sox during Theo Epstein's brief tenure interruption in late 2005 had plenty left in the tank, and the Fish gave them up eagerly.

    Beckett had won the 2003 World Series MVP award with Lowell as his third baseman. Lowell would go on to win the 2007 award as a Red Sox, with Beckett winning 20 games along the way that year. The deal still creates buzz; some people actually think it was a bad deal, despite the pay-off of a second World Series title for Bostonians. That's an interesting viewpoint.

34. Kenny Lofton to Atlanta Braves, David Justice, Marquis Grissom to Cleveland

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    This move drew attention both for the star power of the players involved, and for the unusual circumstances of the deal itself.

    There was no obvious buyer or seller in the deal; it seemed a challenge trade. Those are rare in all cases, but especially late in Spring Training. The Indians and Braves consummated the deal on March 25, 1997. 

    Lofton was the best player in the deal, and the Braves did get Alan Embree to flesh out their perpetually problematic bullpen. The team had no reason to expect that it would want for power, though ultimately, it did.

    The trade made sense; it was just strange. It worked out better for the Indians, to be sure, as they rode their two new outfielders to a World Series berth. Lofton struggled to stay healthy, though, and the Braves could not beat divisional foe Florida for the right to face Cleveland in the Fall Classic.

33. Curt Schilling to Arizona Diamondbacks, Vicente Padilla to Phillies

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    Signing Randy Johnson was a major splash for the expansion upstarts of the Arizona desert in 1999, but they weren't done. Feeling they could get over the hump with another elite pitching addition, the Diamondbacks made a blockbuster trade the following summer, adding Curt Schilling of the Phillies.

    There might never have been a better duo in a starting rotation. Johnson and Schilling brought Arizona a World Series ring, and finished one-two in NL Cy Young voting in both 2001 and 2002. It cost them a premium package of prospects, but Schilling's arrival proved how serious Arizona was about winning immediately.

32. Bartolo Colon Cost What?!

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    The Montreal Expos won the sweepstakes for the services of one Bartolo Colon in the summer of 2002. In the same way, Pyrrhus of Epirus won the Battle of Asculum. 

    To land Colon, the Expos gave up Brandon Phillips, Grady Sizemore, Cliff Lee and Lee Stevens. Not all of those players were regarded as well as they deserved, but even so, the deal raised eyebrows right away. Colon did pitch well for Montreal, but failed to draw them out of obscurity. The team finished at 83-79.

31. Vernon Wells, Mike Napoli and Ancient Questions

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    What happens when an unstoppable force meets an immovable object? Sometimes, they just switch places and go on as they were.

    At least, that was the story last winter. Vernon Wells' seven-year, $126-million contract still promised him $86 million over four years with the Toronto Blue Jays. If any contract in baseball were immovable, surely that was it.


    Angels GM Tony Reagins not only agreed to acquire Wells from Toronto, but also gave up unstoppable force Mike Napoli. Napoli went on to post a .320/.414/.631, albeit not for Toronto, and could well have been the World Series MVP. This deal basically got Reagins fired all by itself.

30. The Infamous White Flag White Sox

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    The photo above features four key cogs in the Chicago White Sox pitching staff, circa 1997. Two of them, though, suddenly disappeared at midseason.

    Wilson Alvarez and Danny Darwin (plus Roberto Hernandez, not pictured) went to the San Francisco Giants on July 31 of that year for a pack of minor-league talents.

    It wasn't a terrible deal, objectively. The White Sox got three players who would eventually make positive contributions to their club. The timing was awful, though. Chicago trailed in the AL Central by only three games at the time, and giving away those three hurlers sealed their fate as non-competitors for the rest of the year.

29. Moises Alou to Houston Astros, Frustration to Florida Marlins Fans

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    It really is tragic that Wayne Huizenga so totally misunderstood the economy of Major League Baseball. He somehow expected the good folks of Miami to intuitively foresee the fledgling team's improbable World Series run in 1997. When they failed to flock to the park during the season, Huizenga quietly made a monstrous choice.

    Within two weeks of the team winning the Series, Huizenga began a vengeful dismantling. He ordered the budget slashed to such depths that, on Veteran's Day, the Marlins dealt Moises Alou for Manuel Barrios and Oscar Henriquez of the Houston Astros, plus a player to be named later. That turned out to be Mark Johnson.

    It was a bad trade from the moment it was made, and the baseball world mourned the death of a fragile romance that had once encircled the game. It had been in danger for years by then, but the Marlins' rise and fall illustrated how jaded the business had become.

28. Kevin Brown to San Diego Padres, Derrek Lee and Others to Marlins

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    Like the 1998 Astros (who won 102 games and the NL Central), the 1998 Padres owe a large debt to Huizenga's avarice.

    They got Kevin Brown from Florida a few weeks after the Astros nabbed Alou, paying a slightly higher price but still virtually stealing the ace right-hander. Derrek Lee was a gem, but Brown was a superstar, and when he went, the floodgates flew open. The Marlins would trade a handful of other key contributors in smaller deals before the end of that offseason.

27. Nomar Garciaparra to Cubs, a Fresh Mix to Boston Red Sox

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    This deal is famous in 2012 for reasons very different from the ones for which it was famous when it went down at the 2004 trade deadline.

    The Chicago Cubs wanted Nomar Garciaparra; they wanted him badly. They hoped adding an extra bat of his caliber would make them unstoppable down the stretch, and send them to the playoffs for the second year in a row.

    The Boston Red Sox wanted to get the hell rid of Nomar Garciaparra. He seemed disinterested on days when he could not play, and thanks to accumulating injuries, those days accounted for a large percentage of all days that spring and summer. They needed consistency, and a defensive boost.

    The Minnesota Twins and Montreal Expos didn't want anything too desperately; they were just puppet franchises. The Cubs and Red Sox called them into the negotiations in order to satisfy the needs of all involved, and the final result was a rare true blockbuster in midseason. It worked out better for Boston than for the Cubs, of course.

26. Gary Carter to New York Mets, Four Players to Montreal Expos

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    Darryl Strawberry, Keith Hernandez, Sid Fernandez and Doc Gooden were too good a core to waste, yet the 1984 New York Mets won only 90 games and missed the playoffs. They had a gaping hole at catcher, and every possible motivation to fill it.

    That made this deal easy to see coming, but it was big news nonetheless. The Mets got their man, changed their offensive outlook, and by the end of Carter's second season, they got their reward.

25. Dontrelle Willis, Miguel Cabrera to Detroit Tigers, Prospects to Marlins

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    It should never be a surprise when the Marlins unload an expensive star player, but this deal ended up looking strange. The Tigers got Miguel Cabrera, but announced an intention to keep him at third base.

    Dontrelle Willis had had a miserable year in 2007, yet the Tigers clearly prioritized him as well, because they signed him to a three-year contract extension shortly after the trade happened.

    Cabrera worked out, though not right away. Willis was an unmitigated disaster. In the meantime, the Tigers sent Florida a package of very strong prospects, but none of them found success in Florida. Nonetheless, when it all went down, this looked like a big winner for both sides.

24. Rickey Henderson to Yankees, Five Solid Youngsters to Oakland A's

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    Eric Plunk was dealt to the Oakland Athletics for Rickey Henderson in 1984—then back to the New York Yankees in 1989, for Henderson again. It was not straight-up in either case, of course.

    It wasn't exactly the 1950s anymore, and in 1984, the Yankees ponied up some serious top-end talent in order to get the game's most electrifying leadoff man. It was a major deal, though, and it worked out for New York, in that Henderson posted a .419 OBP and stole 80 bases for them in 1985.

23. Tris Speaker to Cleveland Indians, Sam Jones to Boston Red Sox

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    Much is made of a certain, more fiscally motivated Red Sox trade in the Dead Ball era, but it ought to be noted that the Sox also dealt a 27-year-old Tris Speaker after winning the 1915 World Series.

    Speaker was very much in his prime, and the trade was met with a certain allotment of teeth-gnashing and garment-rending in Boston even when it happened. If there were some who saw merit in the trade, Speaker probably damaged their faith when he led the AL in batting average, OBP and slugging in 1916.

22. Mark Teixeira to Atlanta Braves, Two AL Pennants to Texas Rangers

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    Trading for Mark Teixeira made good sense for the Atlanta Braves at the July 31 deadline in 2007. They were 56-51 at the time, and just three-and-a-half games out of first place. Even better, they had Teixeira through 2008.

    Unfortunately, the team only went 28-27 from then on, and the next season, Atlanta traded Teixeira in July to the Angels.

    That's not the worst news.

    The worst news is that the Braves also gave up a king's ransom to land Teixeira.

    Elvis Andrus should have been starting at shortstop in Atlanta these past three years. Matt Harrison and Neftali Feliz are sensational pitchers whom the team would not have had to rush, but who could have made enough talent expendable for the team to get a more long-term offensive asset at some point. Jarrod Saltalamacchia was expendable already, but the Braves ended up getting a rental player for him.

    It didn't end well for Atlanta. The Rangers, on the other hand, leveraged those new players into two consecutive World Series berths.

21. Mark McGwire to St. Louis in Reunion with Tony La Russa

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    Forget all we know about McGwire's methods now. Back in 1997, all the baseball world knew about McGwire was that his home runs went farther than any home runs anyone else had ever hit, and that he was as dangerous a slugger as there had been in baseball in 30-plus years.

    Tony La Russa had always believed in McGwire, even through thin times, so it was no surprise (once the A's started shopping Big Mac) that the Cardinals went out and did what it took to secure McGwire. The rest is history.

20. Roy Halladay to Philadelphia Phillies, Kyle Drabek and Company to Blue Jays

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    The Phillies had a sturdy lineup and a shiny new ace when they reached the 2009 World Series, but it wasn't enough. They lost to the New York Yankees. That provided plenty of fuel for GM Ruben Amaro to amend the status quo. 

    The ace they had was Cliff Lee, but at the time, the Phillies felt they could not afford to keep Lee and add a premier arm atop the rotation. Therefore, if Amaro were to make a big deal, it needed to be substantial enough to justify also dealing Lee.

    He found that trade.

    The Phillies landed Roy Halladay, the best pitcher in baseball. They gave up a very impressive batch of prospects, but got a few in return when Amaro wheeled around and dealt Lee to the Seattle Mariners in order to facilitate the trade.

    This sort of shuffle-the-deck, big-money and big-name brokerage had been the exclusive purview of the Red Sox and Yankees for years, so this trade announced the Phillies' intention to enter that elite circle.

19. Carlos Beltran to Houston Astros, John Buck and Mark Teahen to Royals, Etc.

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    In 2004, Carlos Beltran was at the very height of his considerate abilities. He hit 38 home runs, stole 42 bases and was caught trying to steal just three times that year. 

    He was exactly what the Houston Astros needed.

    When they traded for Beltran on June 24, they were 38-34. They stood in fourth place in the NL Central, fifth in the Wild Card and had the eighth-best record in the National League.

    They had Roy Oswalt, Roger Clemens, Brad Lidge, Lance Berkman, Jeff Bagwell, Jeff Kent, Craig Biggio and (though he was injured for much of the first half) Andy Pettitte. Yet, they were only narrowly contending.

    The impact of the Beltran deal was immediate, and enormous.

    From that point onward, the Astros won 54 of their final 90 games, and despite insane hot streaks down the stretch from both the Braves and the Cardinals, Houston won the Wild Card, before taking the Cardinals to a seventh game in the NLCS.

18. Randy Johnson to Houston Astros, Freddy Garcia, Others to Seattle Mariners

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    The Astros had a pretty okay grip on a playoff berth when they traded for Randy Johnson as a three-month rental at the 1998 trading deadline. Still, they knew they would need more elite pitching in order to go anywhere in October.

    To that end, Houston sent Freddy Garcia, John Halama and Carlos Guillen (that's not a glamorous group, by the way, but all became solid contributors to a Seattle club that won 116 games in 2001) to the Mariners in exchange for Randy Johnson. He delivered, too, pitching to a 1.28 ERA and a 10-1 record in 11 starts down the stretch.

17. Ken Griffey, Jr. to Cincinnati Reds, Mike Cameron, Others to Mariners

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    Griffey made it clear not long after Johnson left: He didn't care much for the direction in which the Mariners were headed, and he wanted badly to go home and play for the Cincinnati Reds.

    Griffey had the right to block all trades, so by declaring his preferred landing spot, he stole a lot of leverage from Seattle.

    Still, the Mariners managed to snag useful center fielder Mike Cameron in exchange for Griffey, and this trade, too, helped build the championship-caliber club the Mariners fielded for a few years post-superstars.

    The merchandising frenzy created by Griffey's move to the Reds proved that the Reds were wise to acquire the future Hall of Famer, even if they never got his best.

16. Fred McGriff to Atlanta Braves in Huge Race

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    On July 22, 1993, the Atlanta Braves trailed the San Francisco Giants by 10 games in the NL West. Fortunately, help was on the way.

    Atlanta ponied up and made a huge acquisition that week, adding first baseman Fred McGriff from the San Diego Padres. McGriff hit .310/.392/.612 and the Braves went 49-16 down the stretch. They won 104 games; the Giants won 103. It was among the greatest races in MLB history.

15. Carter, Roberto Alomar to Toronto Blue Jays, McGriff, Fernandez to Padres

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    This deal got all kinds of publicity as one of the most daring in years, and that was before everyone knew exactly how good Alomar would turn out to be.

    McGriff and Carter each make their second appearance on this list here, which illustrates nicely each man's career: They seemed to drift around more than any players of their production profile deserved to.

    They often seemed replaceable to the teams for whom they played, and maybe those clubs were right, but there's a lot to be said about continuing to perform and provide steady production despite multiple changes of scenery.

14. Nolan Ryan, Three Others to Angels, Jim Fregosi to Mets

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    Admittedly, Nolan Ryan was not yet that Nolan Ryan in December 1971. He struggled to a 10-14 record that season.

    Jim Fregosi, meanwhile, had had a rough year after a string of very good ones. It was a deal that seemed to make sense, though the presence of both Fregosi and Ryan made it a publicized and risky one.

    All that risk blew up in the Mets' faces. Ryan, at 25 years old, struck out 329 batters in 1972, and had a 2.28 ERA. Fregosi, at 30 years old, didn't bounce back, and was dealt a year-and-a-half after the Mets acquired him.

13. Frank Robinson to Orioles, Milt Pappas and Others to Cincinnati Reds

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    The best reason for the Reds to have dealt a 29-year-old Frank Robinson to the Orioles in 1965 was that he was only great from 1963-65, not the absolute best hitter in the National League. It was a terrible decision from the moment the Reds let Robinson go, and people took notice: Robinson was a six-time All-Star, 1956 NL Rookie of the Year and 1961 NL MVP, after all. 

    If it looked bad at the time, though, it would only get worse for Cincinnati. Robinson reemerged as the game's greatest slugger in 1966, and won the Triple Crown. 

12. Roger Clemens to Yankees, David Wells, Others to Blue Jays

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    Roger Clemens wanted to be a Yankee. He made no secret of it. After two years of dominance in Toronto post-Red Sox, Clemens got his wish from his new team.

    The Yankees had to bundle David Wells, Homer Bush and more to land Clemens, but when they did, it proved well worth it.

    This move became characteristic of the Yankees' behavior for the next several seasons, though, and led to their brief organizational decay. They simply bought the best player available either in trade or in free agency, even when that player cost more than he was worth.

11. Houston Astros, San Diego Padres Swap 12 Players

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    Not since the aforementioned (collusive) Yankees-Athletics swap of 1957 had 12 players been involved in a trade, but in late December 1994, the Astros and Padres found the right equilibrium to make this huge deal happen.

    Ken Caminiti and Steve Finley headlined the deal in terms of San Diego's draw, while for the Astros, Derek Bell, Doug Brocail and Ricky Gutierrez made the deal work. In the long, bitter winter, under clouds of stalled labor talks, this trade became a whimsical (and intellectually impressive) ray of light.

10. Babe Ruth Sold to Yankees

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    This deal gets a lot of different spin, and little of it really reflects the sentiment of the time.

    Fans did not openly weep or revolt when this trade happened.

    Ruth was a great young pitcher who had had World Series success, and it was certainly on the radar (that's another misconception; this wasn't an enigmatic deal) as a transaction of note. Still, no one knew Ruth would be quite what he became when Harry Frazee sold his star southpaw to the enemy.

9. Mannywood Comes to Dodgertown

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    What a circus this situation was.

    After Ramirez more or less shut it down midseason on the 2008 Red Sox, Boston found a creative solution. They sent Ramirez to the Dodgers, got Jason Bay out of the Pirates, and both LA and Boston poured fairly useless pseudo-prospects into the Pittsburgh Pirates in order to get it all done.

    It worked out, and to great and glorious applause all around, but this trade got a ton of hype long before it actually got done, too. Once it was, Ramirez's gigantic ego (it had outgrown the small left field at Fenway) swelled to unprecedented proportions. Mannywood was born.

8. CC Sabathia Changes Course of Brewers Franchise

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    The Milwaukee Brewers almost snapped a long playoff drought in 2007, but they fell short. When Yovani Gallardo got hurt on Opening Day in 2008, it seemed like the team might never get over the hump.

    They leaped the hump in a single bound just two-and-a-half months later. The Brewers more or less mortgaged a thin farm system to land CC Sabathia, but when they got him, they went on a run that changed the outlook of the franchise for good.

    Sabathia went 11-2 for Milwaukee, and led them to the playoffs. The trade became the story of their season, and deservedly so. The fans came out to see this aggressive young team play, and they haven't stopped coming.

7. Steve Carlton to Phillies, Rick Wise to St. Louis Cardinals

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    Pitchers and catchers were already reporting in 1972, when the St. Louis Cardinals and Philadelphia Phillies executed a challenge trade.

    It sent two pitchers in their mid-20s on passing buses, with Steve Carlton landing with the Phillies and Rick Wise heading to the Cardinals. Carlton had won 20 games the previous year, but with unimpressive, fairly average component numbers. The Cardinals, though, wanted Wise.

    The Phillies made the right choice.

    Carlton won the Cy Young award despite the crumminess of the rest of his squad in 1972, with 27 wins, a sub-2.00 ERA and nearly 350 innings of work to his name. He ended up in the Hall of Fame. By 1974, Rick Wise ended up in Boston.

6. Tom Seaver to Cincinnati Reds, Broken Hearts to New York Mets Fans

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    The Mets weren't going anywhere in 1977, and the Reds were.

    This deal made sense. All things considered, the team didn't do too badly either. They got two second-division corner outfielders, a solid utility infielder and a back-end starting pitcher for a 32-year-old hurler with noticeably less zip on his fastball.

    That didn't matter much. Mets fans had fallen in love with Tom Seaver over a decade earlier, and the affair ended too soon for their tastes. The deal was wildly unpopular.

5. Mike Piazza Is a Marlin for a Few Days

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    It was almost as if the Marlins simply played puppet for the Mets and Dodgers in May, 1998.

    Already well into the destructive post-championship phase, they still had some dangling assets available.

    When Mike Piazza became available and the Mets initially fell short of the price demanded by Los Angeles, Florida saw an opportunity. They shipped everything the Dodgers could have wanted (Gary Sheffield, Bobby Bonilla, Jim Eisenreich, Charles Johnson and Manuel Barrios) to the West Coast in exchange for Piazza and Todd Zeile.

    Eight days later, Piazza was a Met, netting the Marlins three high-profile prospects. At the deadline that year, Florida finished its dirty deed by dealing Zeile to the Rangers.

4. Rocky Colavito to Detroit Tigers, Harvey Kuenn to Cleveland Indians

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    Rocky Colavito was a New York native, but the people of Cleveland took a shine to him as though he were a local kid. Through 1959 (at 25 years of age), Colavito put together a stellar .272/.365/.534 line and hit 129 home runs.

    The Indians, however, saw Colavito's batting average as a problem. They dealt him, on the eve of the 1960 season, to Detroit for reigning AL batting champion Harvey Kuenn. Kuenn lacked Colavito's power and patience, but was a .314 career hitter, and the organization felt he would better fit their philosophy.

    Apparently, that expectation was not met, because even after hitting .308, Kuenn was gone a year later. The Indians still have to bear whispers about the so-called "Curse of Rocky Colavito," a fan-favorite sent away too hastily.

3. Alex Rodriguez Moves to New York...and Third Base

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    Everything about this trade was delectable.

    It was as much a scandal as a transaction. It called back to the fore the obscene amount of money Rodriguez made. It brought up the question of whose team the Yankees would be, between Rodriguez and Derek Jeter, and of whether it ought to have been Jeter who moved off shortstop to accommodate the deal. 

    The Red Sox briefly seemed to have the inside track to get a deal done, before leakage of negotiating terms angered the Rangers and sent them running.

    In the end, arguably the most captivating thing about the whole deal was how little Texas got in return: Alfonso Soriano was a great slugger at the time, but a miserable fielder, and a hyper-aggressive base-runner. If Twitter had existed in 2004, Alex Rodriguez would have crashed it.

2. Johan Santana to Mets, Unsatisfactory Prospect Package to Twins

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    The Mets flopped spectacularly in 2007.

    They blew a seven-game lead with 17 to play, which is nigh unprecedented, and it hurt like hell in New York. The Queensmen needed to make a splash and demonstrate their resolve to recover, and they did it in a huge way: Johan Santana came via trade in February, 2008. 

    It hasn't worked out all that well for the team, of course, but the splash this deal made is almost unparalleled in big-league history. Omar Minaya's reputation as a gun-slinging, unabashed high-roller was sealed.

1. Curt Flood, Dick Allen and the Reserve Clause

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    The move would have been high-profile anyway, due to the talent involved, but Curt Flood made sure this trade between the Phillies and Cardinals in 1969 lived on forever in the annals of the game.

    Flood refused to report to the Phillies.

    He had had enough of being treated like what he would later term "a well-paid slave," and was ready to stand up for his rights of self-determination.

    By challenging baseball's reserve clause and shattering the status quo, Flood became a martyr on the altar of free agency. He was black-balled by the league, but within five years, free agency was becoming real for baseball players.

    The defiance, courage and intellect Flood demonstrated all take on more significance in light of the cultural context of his time.

    Flood was a black man, playing in a city in which the spirit of the South (the old, segregated South, at that) was yet alive and well.

    He bore more criticism, and certainly faced greater obstacles to reentry to the league later, than he otherwise would have, due to his race. That issue colored his idea of baseball's systems for player acquisition.

    Ditto Dick Allen, who had a lot more anger inside him but shared Flood's sensitive interior and his bright intellect.

    Allen was an accomplished musician, as graceful off the field as he was violent within the batter's box.

    His involvement in the trade is cursory, but he is as compelling a figure as that era produced, and both he and Flood are remembered too vaguely.

    They changed the game more than once.


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