The 25 Worst MLB Trade Deadline Deals (www.yardbarker.com)

MLB teams always have big decisions to make at the trade deadline that could alter their franchises for the short and long term. And they hope their trades turn out better than these 25 transactions from MLB deadline history.

 

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1988: Yankees trade Jay Buhner to the Mariners for Ken Phelps

1988: Yankees trade Jay Buhner to the Mariners for Ken Phelps

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This trade is one of the most famous in MLB history for being the subject of Frank Costanza’s ire toward

in a 1996 episode of “Seinfeld .” And Frank was right. Phelps hit well for the Yankees down the stretch (.224/.339/551) but saw his stats plummet the following year, while Buhner went on to have a terrific career in Seattle. Playing for the M’s from 1988-2001, he hit 310 career home runs and won one Gold Glove in right field.

 

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1988: Red Sox trade Curt Schilling and Brady Anderson to the Orioles for Mike Boddicker

1988: Red Sox trade Curt Schilling and Brady Anderson to the Orioles for Mike Boddicker

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Bound for the playoffs, Boston traded two promising prospects in Schilling and Anderson for Boddicker. Boddicker certainly did his job after being acquired, posting a 2.63 ERA in 89 innings, almost all as a starter, and then throwing more than 200 innings in each of the next two seasons. However, the O’s got more than fair value in the deal, as Schilling blossomed into one of the game’s best pitchers (albeit many years down the road with other teams), and Anderson played 14 seasons with Baltimore, making three All-Star appearances and hitting 50 home runs in 1996.

 

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1989: Rangers trade Sammy Sosa to the White Sox for Harold Baines

1989: Rangers trade Sammy Sosa to the White Sox for Harold Baines

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Baines was a productive DH for the Rangers over two seasons but certainly not worth the cost of Sosa. Sosa showed good raw power at the time and was eventually traded by the White Sox to the Cubs before the 1992 season for George Bell. The rest is history, as Sosa hit 609 career home runs, including more than 60 home runs twice.

 

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1995: Blue Jays trade David Cone to the Yankees for Marty Janzen, Jason Jarvis, and Mike Gordon

1995: Blue Jays trade David Cone to the Yankees for Marty Janzen, Jason Jarvis, and Mike Gordon

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These days Cone is acclaimed in New York as a broadcaster, but he was also a terrific pitcher for his time with the Yanks. The right-hander made two All-Star appearances while pitching parts of six seasons for the Yankees after getting traded at the 1995 deadline, including a 20-win season in 1998. He also helped the team win four World Series, while no prospects in Toronto’s return panned out.

 

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1997: Giants trade Keith Foulke and Bob Howry to the White Sox for pitching

1997: Giants trade Keith Foulke and Bob Howry to the White Sox for pitching

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San Francisco strengthened its pitching staff by acquiring Wilson Alvarez, Danny Darwin and Roberto Hernandez from Chicago in 1997, but it was at a great cost. Foulke and Howry were among a package of six players and went on to become solid major league relievers. Foulke recorded 191 career saves and helped the 2004 Red Sox break the curse, while Howry had a 3.84 ERA and 66 saves over 13 seasons. San Francisco got little from its acquisitions and was swept by the Marlins in the 1997 LDS.

 

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1997: Mariners trade Derek Lowe and Jason Varitek to the Red Sox for Healthcliff Slocumb

1997: Mariners trade Derek Lowe and Jason Varitek to the Red Sox for Healthcliff Slocumb

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It seems unlikely Boston would have broken the curse and won the World Series in 2004 without this trade. The Red Sox took advantage of Seattle’s desperation for a reliever by acquiring Lowe and Varitek. Lowe made two All-Star appearances in eight seasons with the Red Sox and was a key member of the team’s 2004 World Series run. Varitek eventually became team captain and had 15 productive seasons behind the plate with three All-Star appearances. Slocumb had a 5.79 ERA at the time of the trade but did pitch a bit better after the deal as Seattle’s closer. He stuck around Seattle for one more season, with a 5.32 ERA in 1998.

 

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1998: Dodgers trade Paul Konerko to the Reds for Jeff Shaw

1998: Dodgers trade Paul Konerko to the Reds for Jeff Shaw

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One of the game’s top closers, Shaw was shipped to the Dodgers at the 1998 deadline for two promising prospects. Shaw was a solid closer in L.A. for the next few years, but the cost was great. Konerko briefly played for the Reds before he was traded to the White Sox for Mike Cameron after the 1998 season and went on to have a tremendous career with 439 home runs and six All-Star appearances. Cameron was a good player in his own right over 17 seasons but spent only one season in Cincinnati before getting traded to Seattle in the Ken Griffey Jr. deal.

 

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2000: Indians trade Richie Sexson to the Mariners for pitching

2000: Indians trade Richie Sexson to the Mariners for pitching

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A top first base prospect and 31 home run hitter in 1999, Sexson was blocked in Cleveland by Jim Thome. The Indians used him as a trade chip to acquire Jason Bere, Bob Wickman and Steve Woodard. Among that group, only Wickman proved to be a major asset. Sexson continued to be an elite power hitter for the rest of his career, hitting 30-plus home runs six times and making two All-Star appearances.

 

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2000: Blue Jays trade Michael Young to the Rangers for Esteban Loaiza

2000: Blue Jays trade Michael Young to the Rangers for Esteban Loaiza

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Young wasn’t thought of as a top prospect when the Rangers netted him for Loaiza in 2000. He emerged as one of the game’s best hitters during his career, making seven All-Star appearances and leading the league in hits twice. Young hit .300 for his career over 14 seasons and also hit more than 20 home runs four times. Loaiza did pitch well for Toronto in 2000 (3.62 ERA in 14 starts) but struggled in the Jays rotation the following two seasons.

 

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2003: Marlins trade Adrian Gonzalez to the Rangers for Ugueth Urbina

2003: Marlins trade Adrian Gonzalez to the Rangers for Ugueth Urbina

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Even though Ugueth Urbina helped the Marlins win the 2003 World Series as a key reliever, the cost was excessive. Gonzalez was the first overall pick in the 2000 draft and went on to become a star after leaving Texas. Among his career accolades over 15 seasons were five All-Star appearances, four Gold Gloves and two Silver Sluggers with more than 2,000 hits.

 

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2003: Pirates trade Aramis Ramirez and Kenny Lofton to the Cubs for three players

2003: Pirates trade Aramis Ramirez and Kenny Lofton to the Cubs for three players

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It’s not clear why the Pirates traded Ramirez, their 25-year-old third baseman, but it’s a move they certainly regretted. In return for Ramirez and Lofton, the Pirates received Matt Bruback, Jose Hernandez, and Bobby Hill. None of those players ever made a major contribution in Pittsburgh, while Lofton played well down the stretch in 2003 and Ramirez became one of the Cubs best third basemen ever. Over nine seasons, he hit .294-239-804 and made two All-Star appearances.

 

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2004: Mets trade Scott Kazmir to the Devil Rays for Victor Zambrano

2004: Mets trade Scott Kazmir to the Devil Rays for Victor Zambrano

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The consequences of this trade have long since passed, but Mets fans still curse this deal. Kazmir was one of baseball’s best pitching prospects when the Mets traded him to Tampa Bay for Zambrano. Zambrano had no control, leading MLB in walks twice, and only lasted in the league a few more years as a result. He posted a 4.42 ERA in 201.2 innings over three seasons with the Mets, while Kazmir went on to become the Devil Rays ace and two-time All-Star rep before getting traded five years later.

 

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2006: Astros traded Ben Zobrist to the Devil Rays for Aubrey Huff

2006: Astros traded Ben Zobrist to the Devil Rays for Aubrey Huff

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Zobrist wasn’t a big-time prospect when the Astros traded him for Huff in 2006. After a few years struggling at the plate, Zobrist became one of the game’s top players in 2009 by hitting .297-27-91 with a .948 OPS and continued to be a huge part of Tampa Bay’s emergence through 2014 and won a pair of World Series rings after leaving. Huff finished the 2006 season in Houston, hitting .250-13-38 in 68 games before signing with Baltimore in the offseason.

 

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2006: Brewers trade Nelson Cruz and Carlos Lee to the Rangers

2006: Brewers trade Nelson Cruz and Carlos Lee to the Rangers

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Milwaukee was able to acquire a package of Francisco Cordero, Kevin Mench, Laynce Nix, and Julian Cordero from Texas for Cruz and Lee at the 2006 deadline. While the group was good for Texas, only Cordero was a major contributor in Milwaukee. Cruz became one of the league’s premier power hitters three years later and has been on an elite 11-year power run, and Lee was also productive down the stretch in 2006 before signing with Houston.

 

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2007: Braves trade prospects to the Rangers for Mark Teixeira

2007: Braves trade prospects to the Rangers for Mark Teixeira

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Teixeira was a tremendous player for the Rangers over four-plus seasons, hitting at least 30 home runs four times, but the haul Texas received from Atlanta was franchise-altering. The Rangers got Elvis Andrus, Neftali Feliz, Matt Harrison, Jarrod Saltalamacchia and Beau Jones for Teixeira and Ron Mahay. The group helped the Rangers advance to two World Series, and Andrus remains in Texas as one of its all-time best players.

 

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2008: Cubs trade Josh Donaldson and three other prospects to the A’s for Rich Harden

2008: Cubs trade Josh Donaldson and three other prospects to the A’s for Rich Harden

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Oakland GM Billy Beane sold high on the oft-injured Harden at the 2008 deadline, getting an impressive four-player prospect package in return. Harden was excellent at the end of 2008 (1.77 ERA in 12 starts) but was never the same after that season. The A’s didn’t get great production out of three of the players they received, but Donaldson more than made up for it. The converted catcher finished in the top eight in AL MVP voting with Oakland in 2013 and 2014 before getting traded to Toronto and winning the award in 2015.

 

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2010: Padres trade Corey Kluber and another prospect in a three-way trade to Cleveland for Ryan Ludwick

2010: Padres trade Corey Kluber and another prospect in a three-way trade to Cleveland for Ryan Ludwick

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Cleveland traded starter Jake Westbrook in a three-team deal, netting the Indians a former fourth-round pick in Kluber. Kluber eventually became an ace for the Indians, winning the AL Cy Young in 2014 and 2017.

 

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2011: Rangers trade Chris Davis and Tommy Hunter to the Orioles for Koji Uehara

2011: Rangers trade Chris Davis and Tommy Hunter to the Orioles for Koji Uehara

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Uehara was a dominant reliever for two years in Baltimore leading up to his trade to Texas. He continued to pitch well, but Baltimore’s acquisition of Davis and Hunter set the team up to compete for the next few years. Hunter was a solid reliever for the Orioles, while Davis led the AL in home runs in 2013 and 2015.

 

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2012: Angels trade Jean Segura and two other prospects to the Brewers for Zack Greinke

2012: Angels trade Jean Segura and two other prospects to the Brewers for Zack Greinke

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The Angels added Greinke for the 2012 stretch run before he left in free agency. While he was a solid contributor (3.53 ERA in 13 starts), they gave up a great future piece in Segura. The shortstop went on to become a star in Milwaukee the following year and continues to be one of the game’s most consistent infielders, making two All-Star appearances and leading the NL with 203 hits in 2016.

 

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2012: Rangers trade Kyle Hendricks to the Cubs for Ryan Dempster

2012: Rangers trade Kyle Hendricks to the Cubs for Ryan Dempster

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The Cubs traded the 35-year-old Dempster to Texas for a middling pitching prospect in 2012 as they continued their rebuild. Dempster had a 2.25 ERA in 16 starts before the trade but was terrible in Texas, posting a 5.09 ERA in 12 starts. Hendricks arrived to the majors two years after the trade and was much better than expected, posting a 3.14 ERA over 162 starts over his first six MLB seasons despite subpar velocity.

 

2013: Orioles trade Jake Arrieta and Pedro Strop to the Cubs for Scott Feldman

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Baltimore was willing to give up two pitchers who weren’t fulfilling expectations for one having a career year in Feldman. Feldman closed out the regular season with a 4.27 ERA in 15 starts, but Baltimore likely regretted the move after what Arrieta and Strop produced in Chicago. Arrieta became an ace the following year and won the NL Cy Young in 2015. He had a remarkable 2.73 ERA in 128 starts with the Cubs. Strop is still going strong in the Cubs pen, with a 2.78 ERA and 28 saves in 390 appearances over seven seasons.

 

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2015: Braves trade seven players to the Dodgers for Hector Olivera and prospects

2015: Braves trade seven players to the Dodgers for Hector Olivera and prospects

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The Dodgers pulled off an unbelievable heist in 2015 in a trade that also involved Atlanta and Miami. Going to L.A. were Alex Wood, Jose Peraza, Jim Johnson, Luis Avilan, Bronson Arroyo, Mat Latos and Mike Morse. None of the prospects the Dodgers traded has panned out, and Olivera’s MLB career effectively ended after h e got into trouble off the field. Wood pitched like an ace at times for L.A. from 2015-2018, while Avilan was also a productive part of its bullpen.

 

2016: Marlins trade Luis Castillo, Josh Naylor and two pitchers to the Padres for Andrew Cashner and prospects

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The Marlins curiously tried to make a run in 2016, acquiring Cashner at the deadline. The hard-throwing right-hander couldn’t have pitched much worse, with a 5.98 ERA in 52.2 innings, and the Marlins finished well out of the playoff picture. Along with Castillo and Naylor, Miami traded pitchers Jarred Cosart and Carter Capps. Castillo has gone on to become an ace, albeit after the Padres traded him to Cincinnati for Dan Straily, and Naylor could also have a bright future as a hitter. The Marlins did receive pitchers Tayron Guerrero and Colin Rea in the deal, who have both made major league contributions.

 

2016: Nationals traded Felipe Rivero and Taylor Hearn to the Pirates for Mark Melancon

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Melancon established himself as one of the best closers in the game, but the Pirates played the long game with his pending free agency and cashed in at the trade deadline. In return, Pittsburgh received a struggling young reliever in Rivero (later known as Felipe Vazquez) who emerged as the team’s closer just one year later. Vazquez was a dominant closer before running into major legal trouble in 2019. Hearn also became one of Pittsburgh’s best pitching prospects before getting shipped to Texas in 2018 for Keone Kela.

 

2018: Pirates trade Tyler Glasnow, Austin Meadows, and Shane Baz to the Rays for Chris Archer

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It was unclear if the Rays would finally trade Archer in 2018, with at least one more year of team control remaining and still sporting a competitive team. They were apparently blown away by the Pirates offer, getting two of Pittsburgh’s most talented young players and their 2017 first-round pick. Glasnow and Meadows have been even better than hoped since the deal. Glasnow had a dominant 2019 season with the Rays, though he’s missed time with injury, while Meadows was an All-Star in 2019. Archer has floundered in Pittsburgh and forced to miss all of 2020 due to injury.



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