MLB Trade Deadline: Every MLB Team's Greatest Trade of All Time
The MLB non-waiver trade deadline is now just over two weeks away, and teams are busily preparing to either bolster their teams for short-term success or set long-term objectives.
Not every trade turns out to be a win-win for both sides—oftentimes deals are conducted based on a belief that a player will thrive with a new organization, and history clearly shows us that's not always the case.
Previous performance can also be a factor in an important trade. For a contending team, it often relies on a player who has shown the ability to come through in the clutch. That particular team may be willing to deal a prospect or two just to acquire that clutch performer.
Whatever the case, trades have been a part of the fabric of Major League Baseball since its inception. We will take a look at the greatest trades in each MLB team's history as we patiently await what lies ahead over the next two weeks.
Arizona Diamondbacks: Curt Schilling
Diamondbacks Traded: SP Omar Daal, RP Nelson Figueroa, 1B Travis Lee and SP Vicente Padilla
Phillies Traded: Curt Schilling
Date: July 26, 2000
In late July 2000, the Arizona Diamondbacks pulled off a five-player trade with the Philadelphia Phillies, acquiring starting pitcher Curt Schilling for Omar Daal, Nelson Figueroa, Travis Lee and Vicente Padilla.
Both Lee and Padilla did at least contribute something for the Phillies during their time there, Lee with 20 HR and 90 RBI in 2001 and Padilla with 14-win seasons in 2002 and 2003.
However, Schilling gave the Diamondbacks one of the most formidable 1-2 starting rotations in the National League along with Randy Johnson, and together the two helped the Diamondbacks win their only World Series championship in 2001.
Atlanta Braves: John Smoltz
Braves Traded: Doyle Alexander
Tigers Traded: John Smoltz
Date: Aug. 12, 1987
This one was pretty much a no-brainer.
In mid-August 1987, the Detroit Tigers were making a push to overtake the Toronto Blue Jays at the top of the AL East and acquired veteran right-hander Doyle Alexander from the Atlanta Braves for young pitching prospect John Smoltz.
Alexander was very helpful to the Tigers for the rest of the season, posting a 9-0 record and 1.53 ERA down the stretch to help the Tigers capture the AL East title. However, Alexander was out of baseball two years later.
Smoltz teamed with Greg Maddux and Tom Glavine for many years to lead the Braves to 14 consecutive NL East titles and a World Series championship in 1995. Smoltz is the only man in MLB history to record 200 wins and 150 saves.
The Tigers gained in the short term with Alexander's performance for the rest of the 1987 season but in the long run missed out on what turned out to be an outstanding career for Smoltz—one that will likely put him in the Hall of Fame.
Baltimore Orioles: Frank Robinson
Orioles Traded: SP Milt Pappas, RP Jack Baldschun and OF Dick Simpson
Reds Traded: RF Frank Robinson
Date: Dec. 9, 1965
Again, pretty much a no-brainer.
Cincinnati Reds GM Bill DeWitt, in explaining the trade that sent Frank Robinson to the Orioles for Milt Pappas, Jack Baldschun and Dick Simpson, called Robinson "an old 30."
Robinson showed DeWitt the following year that "an old 30" can still get the job done.
Robinson won the American League Triple Crown and MVP Award, helping the Orioles win their first-ever World Series championship in 1966.
Boston Red Sox: Orlando Cabrera and Doug Mientkiewicz
Red Sox Traded: SS Nomar Garciaparra and OF Matt Murton to Cubs
Cubs Traded: RP Francis Beltran, SS Alex Gonzalez and IF Brendan Harris to Expos, SP Justin Jones to Twins
Twins Traded: 1B Doug Mientkiewicz to Red Sox
Expos Traded: SS Orlando Cabrera to Red Sox
Date: July 31, 2004
It was a complicated four-team, eight-player trade, but one that netted the Boston Red Sox their first World Series championship since 1918, ending a famous 86-year drought.
The trade of the popular Nomar Garciaparra originally was not met with joy by Sox fans. However, Cabrera and Mientkiewicz solidified the infield defense for the Sox, and Cabrera's bat down the stretch was a huge factor as well.
The 1997 trade that netted the Red Sox catcher Jason Varitek and pitcher Derek Lowe from the Seattle Mariners for relief pitcher Heathcliff Slocumb was a close second and in the long term was a much better deal.
However, the Cabrera/Mientkiewicz deal sealed the deal solely for breaking a longstanding curse in Boston.
Chicago Cubs: Ryne Sandberg
Cubs Traded: SS Ivan de Jesus
Phillies Traded: 2B Ryne Sandberg and SS Larry Bowa
Date: Jan. 27, 1982
At the time of the trade, it looked like the Philadelphia Phillies and Chicago Cubs were essentially trading shortstops, with the Phillies throwing in a second baseman whom they had apparently given up on.
Sandberg had gotten his feet wet for the Phillies in a brief September call-up in 1981, but they elected to include him in the deal nonetheless.
The result? Sandberg became one of the best second basemen in the history of baseball.
Chicago White Sox: Nellie Fox
White Sox Traded: C Joe Tipton
Athletics Traded: 2B Nellie Fox
Date: Oct. 19, 1949
Second baseman Nellie Fox had spent three seasons with the Philadelphia Athletics but couldn't break through the lineup as an everyday player. Following the 1949 season, Fox was traded to the Chicago White Sox for backup catcher Joe Tipton.
Fox teamed with shortstop Luis Aparicio in the 1950s to form one of the best middle-infield combos in the history of baseball, culminating with Fox winning the AL MVP Award in 1959 and helping the White Sox win their first American League pennant in 40 years.
Cincinnati Reds: Joe Morgan
Reds Traded: 2B Tommy Helms, 1B Lee May and UTIL Jimmy Stewart
Astros Traded: 2B Joe Morgan, OF Ed Armbrister, SP Jack Billingham, CF Cesar Geronimo and IF Denis Menke
Date: Nov. 29, 1971
When Cincinnati Reds GM Bob Howsam pulled off this particular trade following a disappointing 1971 season, the reaction was tepid, to say the least.
Former Cincinnati Enquirer beat report Bob Hertzel was especially vocal about his opinion of the deal, wondering why the Reds would unload the right side of their infield in Helms and May, both of whom were considered excellent offensive contributors.
However, the trade netted the Reds five division titles, three National League pennants and two World Series titles.
Hard to argue against that kind of success.
Cleveland Indians: Tris Speaker
Indians Traded: SP Sad Sam Jones, 3B Fred Thomas and $55,000
Red Sox Traded: CF Tris Speaker
Date: April 12, 1916
Center fielder Tris Speaker was already an established nine-year veteran who had helped the Boston Red Sox win two World Series during his time there. However, Speaker had a falling-out with then-Sox president John Lannin, and Lannin dealt Speaker to the Cleveland Naps (Indians).
In Speaker's first year in Cleveland, he captured his first and only batting title, breaking Ty Cobb's incredible run of nine straight batting titles in the process. Just four years later, Speaker would help lead the Indians to their first-ever World Series championship.
Colorado Rockies: Dante Bichette
Rockies Traded: OF Kevin Reimer
Brewers Traded: OF Dante Bichette
Date: Nov. 17, 1992
The Colorado Rockies hadn't even played a game yet and had already proven that they were adept at pulling off successful trades.
On the same day that they selected outfielder Kevin Reimer in the expansion draft in 1992, they traded him to the Milwaukee Brewers for outfielder Dante Bichette.
It was an early birthday present for Bichette, who turned 29 the following day. He flourished in Colorado for seven seasons, leading the league in home runs and RBI in 1995 and making four All-Star teams. Bichette became one of the most popular players in Rockies history.
Detroit Tigers: Willie Hernandez
Phillies Traded: RP Willie Hernandez and 1B/OF Dave Bergman
Tigers Traded: RF Glenn Wilson and UTIL John Wockenfuss
Date: March 24, 1984
Just prior to the start of the 1984 season, the Detroit Tigers sought to bolster their bullpen, acquiring reliever Willie Hernandez along with first baseman/left fielder Dave Bergman from the Philadelphia Phillies.
Hernandez did a lot more than bolster the bullpen—he won the American League Cy Young and MVP awards in helping to lead the Tigers to their first World Series championship in 16 years.
The Tigers' acquisition of first baseman Norm Cash in 1960 was a close second.
Houston Astros: Jeff Bagwell
Astros Traded: RP Larry Andersen
Red Sox Traded: 1B Jeff Bagwell
Date: Aug. 30, 1990
In late August 1990, the Boston Red Sox were looking to bolster their bullpen for a postseason run, acquiring relief pitcher Larry Andersen just before the waiver trade deadline. In return, the Houston Astros received prospect first baseman Jeff Bagwell, who had yet to play a game above the Double-A level.
Andersen did help the Red Sox win the 1990 AL East title but was gone the following season. Bagwell simply became one of the greatest hitters in Astros history whose career will likely culminate with a Hall of Fame plaque.
Kansas City Royals: Amos Otis
Royals Traded: 3B Joe Foy
Mets Traded: CF Amos Otis and SP Bob Johnson
Date: Dec. 3, 1969
In the very first official offseason for the Kansas City Royals following their expansion year, executive vice president Cedric Tallis made a move to improve his ballclub, trading veteran third baseman Joe Foy to the New York Mets for young 22-year-old center fielder Amos Otis and pitcher Bob Johnson.
Otis had only 152 major league at-bats at the time of the deal, accumulating a low .178 batting average. Nonetheless, Tallis saw something he liked in the youngster. Turns out that Tallis had an excellent eye.
Otis would flourish in his 14 years with the Royals, being selected to five All-Star teams, collecting three Gold Glove awards and finishing in the top eight in AL MVP Award balloting on four occasions.
Los Angeles Angels: Nolan Ryan
Angels Traded: SS Jim Fregosi
Mets Traded: SP Nolan Ryan, C Frank Estrada, RP Don Rose and RF Leroy Stanton
Date: Dec. 10, 1971
In December 1971 the California Angels made the difficult decision to trade a very popular player. Shortstop Jim Fregosi had been with the Angels since the beginning of the franchise in 1961 and had represented the team as an All-Star on six occasions.
However, they traded Fregosi to the the New York Mets in exchange for starting pitcher Nolan Ryan and three others.
Ryan had been a part of the Mets team that miraculously won the 1969 World Series over the heavily favored Baltimore Orioles. However, the Mets became increasingly frustrated with Ryan's inability to command the strike zone despite his high-90s fastball.
Ryan's eight seasons with the Angels were historic in nature, setting the all-time single-season strikeout record in 1973 and throwing four no-hitters. Ryan also led the American League in strikeouts in seven of his eight seasons in Anaheim.
Los Angeles Dodgers: Pee Wee Reese
Dodgers Traded: RP Red Evans
Red Sox Traded: SS Pee Wee Reese
Date: July 18, 1939
Throughout the history of the Dodgers franchise, they have been one of the best teams in terms of developing homegrown talent.
However, one of the best shortstops in Dodgers history came via trade.
Pee Wee Reese was playing for the Louisville Colonels, a minor league team that had just been purchased by the Boston Red Sox. However, Sox manager Joe Cronin was also the team's shortstop and was unwilling to remove himself from the lineup in favor of the younger Reese, so Cronin persuaded Sox owner Tom Yawkey to trade Reese to the Brooklyn Dodgers.
Reese would play his entire 16-year career with the Dodgers, helping them to win seven National League pennants and the franchise's first-ever World Series championship in 1955.
In addition, Reese was a huge factor in Jackie Robinson's debut in the majors in 1947, breaking MLB's longstanding color barrier. It was Reese's acceptance of and friendship with Robinson that helped him in his transition, and the two would go on to form one of the best defensive middle-infield combinations in baseball history.
Miami Marlins: Mike Lowell
Marlins Traded: P Ed Yarnall, P Mark Johnson and SP Todd Noel
Yankees Traded: Mike Lowell
Date: Feb. 1, 1999
In September 1998, Mike Lowell got his first taste of big league action with the New York Yankees. Just five months later, Lowell was on his way to Florida.
Lowell would become the franchise leader in home runs, runs batted in and runs scored before being shipped to the Boston Red Sox along with Josh Beckett and Guillermo Mota in 2005.
Milwaukee Brewers: Rollie Fingers, Ted Simmons and Pete Vuckovich
Brewers Traded: OF/1B David Green, SP Dave LaPoint, RF Sixto Lezcano and SP Lary Sorensen
Cardinals Traded: RP Rollie Fingers, C Ted Simmons and SP Pete Vuckovich
Date: Dec. 12, 1980
This was absolutely a one-sided deal in favor of the Brewers. Fingers would pay immediate dividends, winning the AL Cy Young and MVP awards in 1981 with a tremendous season—a 6-3 record, 28 saves, 1.04 ERA and 0.872 WHIP. Fingers would contribute another 29 saves the following year in which the Brewers captured their first-ever American League pennant.
Vuckovich was also a key figure on the 1982 pennant-winning team, winning 18 games and the American League Cy Young Award.
Simmons was a veteran catcher who became a clubhouse leader for the Brew Crew after spending 13 seasons with the Cardinals.
Minnesota Twins: Bert Blyleven
Twins Traded: SS Jay Bell, P Curt Wardle, OF Jim Weaver and P Rich Yett
Indians Traded: SP Bert Blyleven
Date: Aug. 1, 1985
For starting pitcher Bert Blyleven, his trade to the Minnesota Twins was a coming home of sorts—his debut came in a Twins uniform in 1970.
Some 15 years later, Blyleven was back in Minneapolis and helped anchor a starting rotation that would help the Twins win their first World Series title in 1987.
New York Mets: Gary Carter
Mets Traded: IF/OF Hubie Brooks, C Mike Fitzgerald, CF Herm Winningham and SP Floyd Youmans
Expos Traded: C Gary Carter
Date: Dec. 10, 1984
In June 1983, the New York Mets pulled off a trade with the St. Louis Cardinals that netted them veteran first baseman Keith Hernandez. Some 18 months later, they landed another great veteran, acquiring catcher Gary Carter from the Montreal Expos.
Carter and Hernandez were the guiding forces that helped lead the Mets to their World Series championship in 1986 over the Boston Red Sox. Carter was an All-Star his first four seasons in New York, adding to his string of 10 consecutive Midsummer Classic appearances.
New York Yankees: Babe Ruth
Yankees Traded: $100,000
Red Sox Traded: Babe Ruth
Date: Jan. 3, 1920
I'm sure that skeptics will point to this as a sale and not a trade, but it was a transaction nonetheless, and one that changed the balance of power in the American League for many years to come.
Babe Ruth was sold to the New York Yankees by Red Sox owner Harry Frazee in order to finance his Broadway play No, No, Nanette. At least that's how the legend goes.
For the next 15 seasons, Ruth put down his pitcher's glove and turned into the most feared hitter in baseball history. The Red Sox fell into immediate disarray after the sale, suffering through decades of losing before finally winning the AL pennant 26 years after Ruth's trade.
Oakland Athletics: Ken Holtzman
A's Traded: OF Rick Monday
Cubs Traded: SP Ken Holtzman
Date: Nov. 29, 1971
In 1971, the Oakland A's were a powerful team with a starting rotation that included Catfish Hunter, Vida Blue and Blue Moon Odom. After the season ended, they added another piece to their rotation—Ken Holtzman.
Holtzman would win 77 games in his four years in Oakland and posted a 4-1 record and 2.55 ERA in three consecutive World Series triumphs for the A's from 1972 to 1974.
Philadelphia Phillies: Steve Carlton
Phillies Traded: SP Rick Wise
Cardinals Traded: SP Steve Carlton
Date: Feb. 25, 1972
In 1971, southpaw Steve Carlton became a 20-game winner for the first time, but it wasn't enough to keep him on the St. Louis Cardinals.
Just prior to the start of the 1972 season, the Cardinals swapped starting pitchers with the Philadelphia Phillies, getting back Rick Wise in return.
Carlton would win 27 games and his first of four Cy Young Award trophies that year for a hapless Phillies squad that only won only 59 games the entire season. However, Carlton's trade set up what would become a dominant Phillies team that would eventually win their first-ever World Series title in 1980.
Pittsburgh Pirates: Andy Van Slyke
Pirates Trade: C Tony Pena
Cardinals Trade: CF Andy Van Slyke, SP Mike Dunne and C Mike LaValliere
Date: April 1, 1987
Just before the start of the 1987 regular season, the Pittsburgh Pirates traded away arguably one of the best catchers in baseball at the time, Gold Glove Award winner and All-Star Tony Pena.
In return, they received 26-year-old center fielder Andy Van Slyke along with pitcher Mike Dunne and catcher Mike LaValliere. Van Slyke would go on to become a Gold Glove Award winner with Pittsburgh himself, becoming the anchor of a great outfield that included Barry Bonds and Bobby Bonilla. Van Slyke was a key contributor in the Pirates' three consecutive NL East titles from 1990 to 1992.
San Diego Padres: Trevor Hoffman
Padres Trade: 3B/OF Gary Sheffield and RP Rich Rodriguez
Marlins Trade: RP Trevor Hoffman, RP Andres Berumen and RP Jose Martinez
Date: June 24, 1993
In the Marlins' expansion season of 1993, they already had closer Bryan Harvey in place, along with emerging reliever Robb Nen. They pulled off a deal with the San Diego Padres, trading reliever Trevor Hoffman and two pitchers for third baseman/outfielder Gary Sheffield and pitcher Rich Rodriguez.
Hoffman would go on to amass 552 saves with the Padres and 601 saves overall in a career that will likely culminate with a Hall of Fame plaque.
San Francisco Giants: Christy Mathewson
Giants Traded: Amos Rusie
Reds Traded: Christy Mathewson
Date: Dec. 15, 1900
In 1900, young Christy Mathewson appeared in six games for the New York Giants. However, they were so unimpressed that they sent Mathewson back to the minor-league Norfolk team, and his contract was then purchased by the Cincinnati Reds.
In mid-December of 1900, the Giants realized the error of their ways, trading veteran pitcher Amos Rusie to the Reds for Mathewson.
Rusie never won another game in the majors—Mathewson won 373 of them.
Seattle Mariners: Randy Johnson
Mariners Traded: SP Mark Langston and SP Mike Campbell
Expos Traded: SP Randy Johnson, RP Gene Harris and SP Brian Holman
Date: May 25, 1989
In 1989, Randy Johnson was a 25-year-old southpaw with a blazing fastball but with no clue where it would land at any time.
The Montreal Expos included Johnson in an exchange of five pitchers with the Seattle Mariners, and for the Mariners, the exchange was clearly in their favor.
Johnson would eventually harness his control, save for a few over-the-head buzzes (Larry Walker, John Kruk) and would win the first of his five Cy Young Awards for the Mariners in 1995.
St. Louis Cardinals: Lou Brock
Cardinals Traded: SP Ernie Broglio, OF Doug Clemens and SP Bobby Shantz
Cubs Traded: LF Lou Brock, RP Jack Spring and P Paul Toth
Date: June 15, 1964
Not only was this the best trade in St. Louis Cardinals history, it was one of the most lopsided trades in MLB history.
Brock would go on to help the Cardinals achieve three National League pennants and two World Series titles, becoming the all-time stolen base leader in the process at the time.
Brock would also collect his 3,000th hit in 1979, becoming only the 14th player in MLB history to achieve the historic feat.
Tampa Bay Rays: Scott Kazmir
Rays Traded: SP Victor Zambrano and RP Bartolome Fortunato
Mets Traded: SP Scott Kazmir and RP Jose Diaz
Date: July 30, 2004
In late July 2004, the Rays and New York Mets exchanged four pitchers, and it's fair to say that the Mets got hosed.
Victor Zambrano won 10 games in parts of three seasons for the Mets, and Bartolome Fortunato made 17 relief appearances before injuries ended his career.
Scott Kazmir would go on to make two All-Star appearances for the Rays, winning 55 games during his time in Tampa.
Texas Rangers: Josh Hamilton
Rangers Traded: SP Edinson Volquez and RP Daniel Herrera
Reds Traded: CF Josh Hamilton
Date: Dec. 21, 2007
By the start of the 2007 season, Cincinnati Reds outfielder Josh Hamilton had finally started to get his life back on track after years of drug abuse had kept him away from the game that he excelled at.
Taken with the first overall pick by the Tampa Bay Devil Rays in 1999, Hamilton finally made his MLB debut with the Reds in 2007, and it was clear from the start that the great potential was still there some eight years after he was drafted.
Nonetheless, the Reds traded Hamilton to the Texas Rangers following his first season, and all Hamilton has done is win an AL MVP Award, win a batting title and make five straight All-Star teams.
Toronto Blue Jays: Roberto Alomar and Joe Carter
Blue Jays Traded: SS Tony Fernandez and 1B Fred McGriff
Padres Traded: 2B Roberto Alomar and OF Joe Carter
Date: Dec. 5, 1990
It's not often that teams engage in a trade in which four prominent players are involved, but that's exactly what happened between the San Diego Padres and Toronto Blue Jays in early December of 1990.
The Blue Jays sent off star shortstop and four-time Gold Glove Award winner Tony Fernandez along with first baseman Fred McGriff, whose star was just beginning to shine.
In exchange, the Jays received second baseman Roberto Alomar, who had become an All-Star for the first time in 1990 with the Padres, along with veteran outfielder Joe Carter.
Alomar and Carter were two of the guiding forces that helped the Jays win back-to-back World Series titles in 1992 and 1993. Alomar would go on to earn induction into the Hall of Fame, and Carter's name will forever be remembered and revered in Toronto for one very big walk-off home run.
Washingon Nationals: Pedro Martinez
Expos Traded: 2B Delino DeShields
Dodgers Traded: SP Pedro Martinez
Date: Nov. 19, 1993
This may be the one deal in Los Angeles Dodgers history that is the most regrettable, but certainly not for the Montreal Expos.
In 1993, 21-year-old Pedro Martinez was being used as a reliever by the Dodgers, and Martinez was pretty good out of the bullpen, posting a 2.61 ERA in 65 appearances.
At the end of the season, the Dodgers sought to bolster their infield and acquired the speedy Delino DeShields, who was coming off another solid year for the Expos. In exchange, the Expos got Martinez.
Four years later, Martinez would win the first of his three Cy Young Award trophies with a masterful season—a 1.90 ERA, 13 complete games and 305 strikeouts.
DeShields' time in Los Angeles was not well spent—he hit just .241 in L.A. before moving on to the St. Louis Cardinals in 1997.
Doug Mead is a featured columnist with Bleacher Report. His work has been featured on the Seattle Post-Intelligencer, SF Gate, CBS Sports, the Los Angeles Times and the Houston Chronicle.