Most lopsided MLB trades in recent memory

ByDan Mullen ESPN logo
Wednesday, July 22, 2015

The MLB trade deadline is less than two weeks away, and that means contenders are looking to add that missing piece and rebuilding teams are searching for the perfect package of prospects that will lead them to glory in years to come. But we're here to remind you that sometimes trades backfire. These are the most lopsided trades of the past 25 years:

1990: Houston Astros get Jeff Bagwell from Boston Red Sox

The entire deal: Astros acquire Jeff Bagwell; Red Sox acquire Larry Andersen.

With a glut of infield prospects including future MVP Mo Vaughn in their system, and a need for bullpen help in their push for the 1990 AL East crown, the Red Sox reached into that deep pool and acquired veteran reliever Larry Andersen from the Astros for Jeff Bagwell.

The deal actually worked out well for the Red Sox in the short term, as Andersen provided them with some solid relief in 1990, posting a 1.23 ERA in 15 appearances before moving on to San Diego following the season. But it was the long-term fallout that made the deal arguably the most one-sided trade in baseball history.

Bagwell, who made an immediate impact in Houston by winning the 1991 NL Rookie of the Year, went on to become one of baseball's best power hitters during a 15-year career with the Astros in which he belted 449 home runs and won the 1994 NL MVP award.

1992: Philadelphia Phillies get Curt Schilling from Houston Astros

The entire deal: Phillies acquire Curt Schilling; Astros acquire Jason Grimsley.

Prior to the 1991 season, the Astros acquired Curt Schilling (along with Steve Finley and Pete Harnisch) from the Orioles in a trade that easily could have found a home on this list had they not given up on the future ace quite so soon.

After watching Schilling struggle to harness his stuff during a walk-proned year pitching out of the Houston bullpen, the Astros sent Schilling to Philadelphia in a straight-up trade for another young pitcher with control problems in Jason Grimsley, who never pitched a major league game with the Astros before being released in 1993.

Given a chance to start early in the 1992 season, Schilling quickly became a top-of-the-rotation pitcher who went on to be a lynchpin in Philadelphia's 1993 World Series teams and made three All-Star teams during his eight full seasons with the franchise.

1997:Boston Red Sox get Pedro Martinez from Montreal Expos

The entire deal: Red Sox acquire Pedro Martinez; Expos acquire Carl Pavano and Tony Armas.

The 1993 deal to bring Pedro Martinez to Montreal worked out very well for the Expos, but the deal that ended his time with the team did not.

After coming over in a straight-up swap for speedy second baseman Delino DeShields, Martinez gave the Expos four great years culminating with his Cy Young-winning 1997 season before financial reasons dictated it was time to trade the ace.

In return for Martinez, Montreal received a pair of serviceable arms in Carl Pavano and Tony Armas, while the Red Sox added a future Hall of Famer who provided Boston with arguably the greatest stretch of pitching dominance baseball has ever seen. Martinez won two AL Cy Young awards, finished runner-up for two more in Boston and ultimately served as the ace of the 2004 team that ended an 86-year World Series drought.

1997: Boston Red Sox get Jason Varitek and Derek Lowe from Seattle Mariners

The entire deal: Red Sox acquire Derek Lowe and Jason Varitek; Mariners acquire Heathcliff Slocumb.

At the 1997 trade deadline, the Mariners knew they needed bullpen help. Badly. What they did to address their relief shortage was perplexing even at the time, as Seattle was willing to give up minor leaguers Derek Lowe and Jason Varitek for the services of a veteran reliever who had a 5.79 ERA pitching out of Boston's bullpen in 1997.

Not surprisingly, Heathcliff Slocumb's time in Seattle wasn't all too memorable -- he left after posting a 5.32 ERA the next season -- but the two players the Red Sox got back for him certainly were in Boston.

Together, Lowe and Varitek combined to make five All-Star teams with the Red Sox and both were members of the 2004 World Series winners, with Varitek also serving as the backstop for Boston's 2007 championship team.

2002: Cleveland Indians get Cliff Lee, Grady Sizemore and Brandon Phillips from Montreal Expos

The entire deal: Indians acquire Cliff Lee, Brandon Phillips, Grady Sizemore and Lee Stevens; Expos acquire Bartolo Colon and Tim Drew.

Yes, the Expos were in the playoff race in 2002. But they were also a franchise in turmoil with an uncertain future in Montreal, so it came as a surprise to many when the team acquired veteran pitcher Bartolo Colon along with Tim Drew midway through the season.

And they paid a very steep price to do so.

Colon did his part upon arriving in Montreal, going 10-4 with a 3.31 ERA, but being dealt to the White Sox after the 83-win Expos fell well short of a playoff spot and the Expos left Montreal for Washington two seasons later.

Meanwhile, the trio of players Cleveland landed in the deal - Cliff Lee, Grady Sizemore and Brandon Phillips -- all went on to stardom.

Lee became an ace for the Indians, forming a devastating 1-2 punch next to CC Sabathia at the top of the rotation and winning the 2008 AL Cy Young award. Sizemore made good on his enormous potential during three consecutive All-Star campaigns in Cleveland before injuries derailed his career. And Phillips became an All-Star caliber second baseman, albeit doing so with the Reds after the Indians inexplicably gave up on the talented infielder and traded him for Jeff Stevens in 2006.

2003: Chicago Cubs get Aramis Ramirez and Kenny Lofton from the Pittsburgh Pirates

The entire deal: Cubs acquire Aramis Ramirez and Kenny Lofton; Pirates acquire Bobby Hill, Jose Hernandez and Matt Bruback.

Third base had long been a revolving door on the north side of Chicago until a July 3, 2003, deal with the Pirates gave the Cubs their answer at the hot corner and a playoff-tested center fielder in a deadline deal that netted little in return for Pittsburgh.

Ramirez's time in Chicago was the key to earning this deal a spot among baseball's most lopsided, but it was Lofton who was the Cubs' primary target at the deadline. Seeking a short-term replacement for injured Corey Patterson, Lofton provided exactly what the Cubs were looking for by hitting .327 in 56 games for the NL Central champions.

Lofton left town following the season, but Ramirez made himself a mainstay in Chicago for years to come and became the team's first third baseman to start an All-Star Game since Ron Santo. All told, Ramirez hit 239 home runs and drove in 806 runs during his seven-and-a-half-year run with the Cubs.

As many of their moves were at the time, the trade was a cost-cutting deal for the Pirates, who were hoping promising prospect Bobby Hill would blossom after coming to Pittsburgh. But that's not how things worked out as Hill played just 184 games as a Buc, hitting .267 with two home runs, before being traded following the 2005 season. Veteran infielder Jose Hernandez also made little impact after the trade, batting just .223 in Pittsburgh and lasting just half of a season with the team.

2003: Minnesota Twins get Joe Nathan, Francisco Liriano from San Francisco Giants

The entire deal: Twins acquire Joe Nathan, Francisco Liriano and Boof Bonser; Giants acquire A.J. Pierzynski.

Hoping to add offense at catcher, the Giants targeted catcher A.J. Pierzynski, who had hit .300 in back-to-back seasons for the Twins at the time of the deal. To get him, they parted with a trio of pitchers in reliever Joe Nathan and prospects Francisco Liriano and Boof Bonser.

At that point, Nathan was nothing more than a middle reliever in San Francisco, but the Twins had bigger plans for him. Handed the ninth inning upon arriving in Minnesota, Nathan saved 260 games and made four All-Star teams before leaving to sign with the Rangers following the 2011 season.

Though Boof Bonser didn't work out for Minnesota, Francisco Liriano gave the Twins another gem in the deal by quickly becoming one of the best pitching prospects in baseball and winning 47 games in the majors from 2005-2011.

On the other side of the trade, the Giants quickly tired of Pierzynski and released him following the 2004 season, his only one with the club.

2006: San Diego Padres get Adrian Gonzalez and Chris Young from Texas Rangers

The entire deal: Padres acquire Adrian Gonzalez, Chris Young and Terrmel Sledge; Rangers acquire Adam Eaton, Akinori Otsuka and Billy Killian.

When the Rangers decided to trade away Adrian Gonzalez, he was blocked by Mark Teixeira and was already looking like a potential bust after being selected by the Marlins with the No. 1 overall pick in the 2000 MLB draft.

It turns out all he needed was a change of scenery and a chance.

Immediately after arriving in San Diego, everything clicked for Gonzalez as he started a five-year run in San Diego with a 24-homer 2006 season and never hit less than that during his time with the team. Before being traded away following 2010 season, Gonzalez hit 161 home runs with the Padres, giving them a rare power threat in spacious Petco Park.

Gonzalez wasn't the only key contributor the Padres acquired from the Rangers, as Chris Young went 31-25 with a 3.70 ERA in four years with the team and was even named an All-Star during the 2007 season.

The players Texas received in the swap didn't fare quite as well. Starter Adam Eaton struggled in his lone season with the Rangers, and closer Akinori Otsuka saved 32 games in 2006 but pitched only one more season in the majors.

2007: Detroit Tigers get Miguel Cabrera and Dontrelle Willis from Florida Marlins

The entire deal: Tigers acquire Miguel Cabrera and Dontrelle Willis; Marlins acquire Cameron Maybin, Andrew Miller, Mike Rabelo, Burke Badenhop, Dallas Trahern and Frankie De La Cruz.

Trading away players as they begin to get expensive is nothing new for the Marlins, and that cost-conscious approach is exactly what led to the 2007 deal that sent Miguel Cabrera and Dontrelle Willis to Motown.

While the Marlins thought they were receiving both quality and quantity in a six-player package headlined by outfield prospect Cameron Maybin and former first-round pick Andrew Miller, the deal didn't work out that way as Maybin failed to live up to the hype before being dealt to San Diego and Andrew Miller struggled with command throughout his time with the team.

Though Dontrelle Willis struggled mightily after moving to the American League, Miguel Cabrera was the gem of the deal for Detroit and his contributions alone, including winning the triple crown and back-to-back AL MVP awards, secured this trade a place among the most lopsided baseball has known.

2007: Texas Rangers get Elvis Andrus, Neftali Feliz and Jarrod Saltalamacchia from Atlanta Braves

The entire deal: Rangers acquire Elvis Andrus, Neftali Feliz, Matt Harrison, Jarrod Saltalamacchia and Beau Jones; Braves acquire Mark Teixeira and Ron Mahay.

Sitting 4 games out of the NL East lead hours before the 2007 trade deadline, the Braves made a bold move to go all-in. And it backfired - big time.

After Mark Teixeira turned down the Rangers' offer of a long-term deal, Texas decided to put the star first baseman on the trade block and was met with an offer it could not refuse.

All in all, Atlanta surrendered five players to get Teixeira and Ron Mahay in a deal they believed made them World Series contenders with Jarrod Saltalamacchia, Elvis Andrus, Neftali Feliz and Matt Harrison headlining Texas' haul.

And while Saltalamacchia never quite lived up to his potential behind the plate, Feliz, Andrus and Harrison all became key contributors during the Rangers' back-to-back World Series runs in 2010 and 2011.

Even though Teixeira hit .317 with 17 home runs in 54 games, Atlanta missed the playoffs in 2007 and he was shipped to the Angels for Casey Kotchman and Stephen Mark midway through the 2008 season.

2008: Toronto Blue Jays get Jose Bautista from Pittsburgh Pirates.

The entire deal: Blue Jays acquire Jose Bautista; Pirates acquire Robinzon Diaz.

You almost have to feel sorry for the Pirates for this one, as they - along with everyone else - had no way of knowing Jose Bautista would go on to become Jose Bautista when they pulled the trigger on this deal sending the then-27-year-old north of the border.

But the result of the deal makes it one of baseball's most lopsided with Bautista blossoming from a journeyman to perennial All-Star after landing with the Blue Jays while the player Pittsburgh received in the deal, catcher Robinzon Diaz, played just 43 games with the Pirates in 2004 and 2005. A six-time All-Star in Toronto, Jose Bautista became the first player in franchise history to hit 50 homers in a season in 2010 and is in the midst of his sixth straight 20+ HR season in 2015.

2008: Baltimore Orioles get Adam Jones, Chris Tillman and George Sherrill from Seattle Mariners

The entire deal: Orioles acquire Adam Jones, Chris Tillman, George Sherrill, Kam Mickolio and Tony Butler; Mariners acquire Erik Bedard.

Coming off an 88-win season, the Mariners wanted another ace to pair with Felix Hernandez. On the heels of consecutive strong seasons in the tough AL East, Erik Bedard fit that criteria and the rebuilding Orioles were willing to trade their best pitcher at his peak value.

The result was a deal that now serves as a cautionary tale for general managers everywhere, as Bedard's health kept him from ever reaching that level again after arriving in Seattle - he never made more than 16 starts in a season with the Mariners -- and of the five players the Mariners parted with in the deal, three of them became All-Stars in Baltimore.

The inclusion of Jones, a five-time All-Star who was the highest-touted player in the deal at the time, tilts the deal strongly in Baltimore's favor as he has become the face of the franchise since joining the Orioles in 2009. Throw in George Sherrill's 51-save run as Baltimore's closer and Chris Tillman's development into a top-of-the-rotation starter for a playoff contender, and you have a deal that has Mariners fans shaking their heads any time Erik Bedard's name is mentioned in the Pacific Northwest.

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