The Most Lopsided Deadline Deals in MLB History

Rick Weiner@RickWeinerNYFeatured ColumnistJuly 29, 2014

The Most Lopsided Deadline Deals in MLB History

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    With the July 31 non-waiver trade deadline quickly approaching, teams around the game are weighing their options.

    Do they go all in, trading away young talent and prospects for an established star? Or do they stay the course, holding on to their youngsters with an eye toward sustained success in the future?

    Let this list serve as a warning: Dealing in prospects is a risky business.

    Nearly every trade that follows looked good on paper but, for one reason or another—usually because those prospects didn't develop as expected—they look completely lopsided today.

    Lists like this pop up on a yearly basis around this time, but nearly every single one of them is inaccurate, including trades that were made weeks before—or after—the non-waiver trade deadline. You won't find that here.

    We've looked at every deal that's gone down from July 24 to July 31 since the current trade deadline was instituted in 1986, and these are the most lopsided of the bunch.

    Let's see who struck gold—and who struck out.


    *Unless otherwise noted, all trade information and statistics courtesy of

July 31, 1989: The Big Unit Gets Traded to Seattle

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    Montreal Got: RHP Mike Campbell and LHP Mark Langston

    One of the premier strikeout artists in the game at the time of the trade, Montreal traded for Mark Langston with the expectation that he'd help them reach the playoffs.

    While he'd put up terrific numbers (24 GS, 12-9, 2.39 ERA, 1.31 WHIP), his arrival wasn't enough to push the Expos into the postseason, as Montreal finished with an 81-81 record, good enough for fourth place in the National League East, 12 games behind the first-place Cubs.

    He'd leave the team after the season as a free agent, signing a five-year, $16 million deal with the California Angels.

    Mike Campbell, who played the part of the always intriguing player-to-be-named-later in the deal, never threw a pitch for the Expos and was traded to the Chicago White Sox less than a year later.


    Seattle Got: RHP Gene Harris, RHP Brian Holman and LHP Randy Johnson

    Seattle was widely lambasted for the deal when it was made, as the Mariners were getting back three relative unknowns for Langston, who had become a fan favorite in Seattle.

    Gene Harris spent parts of four forgettable seasons with the Mariners, pitching to a 5.48 ERA and 1.73 WHIP before being shipped off to San Diego for minor league outfielder William Taylor in 1992—his last season of affiliated ball.

    Brian Holman had a successful three-year run with the Mariners, going 32-25 with a 3.73 ERA and 1.38 WHIP before arm trouble prematurely ended his career at the age of 26 in 1991.

    He's best remembered for coming within one out of a perfect game against Oakland on April 20, 1990, when former Mariner Ken Phelps, pinch-hitting for second baseman Mike Gallego, took him deep.

    For Phelps, who was involved in another lopsided trade that bought Jay Buhner to Seattle, it was the last home run of his career.

    Then there's Randy Johnson, who developed into one of the most dominant pitchers of all time while with the Mariners, appearing in five MLB All-Star Games, winning the 1995 American League Cy Young Award and rewriting the team's record books in the process (which have since been rewritten).

July 28, 1995: David Cone Traded to the New York Yankees

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    New York Got: RHP David Cone

    David Cone would become a key piece of the Yankees' late-'90s dynasty, serving as a leader in the clubhouse and a go-to guy on the mound.

    He'd go 64-40 with a 3.91 ERA and 1.33 WHIP over five-plus seasons in pinstripes, appearing in two All-Star Games, leading the American League with 20 wins in 1998 and, in 1999, throwing the third perfect game in franchise history.

    A four-time World Series champion with the Yankees, Cone was even better in the playoffs than he was during the regular season, winning nine postseason games and posting a spectacular 1.42 ERA and 1.00 WHIP in three World Series starts.


    Toronto Got: RHP Mike Gordon, RHP Jason Jarvis, RHP Marty Janzen

    Of the three pitchers that the Blue Jays got in exchange for Cone, only one—Marty Janzen—ever made it to the major leagues. He'd spend parts of two years with the Blue Jays, going 6-7 with a 6.39 ERA and 1.71 WHIP before he was selected by Arizona in the 1997 Expansion Draft.

    Both Mike Gordon and Jason Jarvis topped out at Double-A in the Blue Jays system, and both were out of baseball by 1999.

July 31, 1997: Derek Lowe and Jason Varitek Traded to Boston

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    Boston Got: RHP Derek Lowe, C Jason Varitek

    The deal that brought two of the most important figures in the franchise's recent history to Boston didn't come together until there was about a half hour left on the clock before the deadline hit, as's Alex Speier recounted with some of the key figures involved back in 2012.

    Lowe would make two All-Star teams while with Boston, first as a closer in 2000, when he led the league with 42 saves, and again in 2002, this time as a starter, when he won 21 games and finished third in the AL Cy Young Award race.

    During Boston's incredible run to end the team's 86-year-old World Series title drought in 2004, it was Lowe who was the winning pitcher in each of the three series-clinching games: Game 3 of the ALDS against the Los Angeles Angels, Game 7 of the ALCS against the New York Yankees and Game 4 of the World Series against the St. Louis Cardinals.

    Varitek would become the heart and soul of the Red Sox franchise for more than a decade, appearing in three All-Star Games, winning two World Series titles and creating too many memorable moments to recount.


    Seattle Got: RHP Heathcliff Slocumb

    The Mariners were desperate to win with a team that featured Ken Griffey Jr., Randy Johnson and an upstart young shortstop named Alex Rodriguez, but the team's bullpen was hemorrhaging runs at an alarming rate, including closer Norm Charlton, who had a 7.27 ERA. 

    So when the chance to add an established closer that was riding a hot streak presented itself—in the 20 games preceding the deadline, Slocumb had converted 11 of 12 save opportunities while pitching to a 2.41 ERA—they jumped at it.

    While he'd convert four of his first five save opportunities for Seattle, Slocumb was ultimately a gigantic bust in Seattle, going 2-9 with a 4.97 ERA and 1.64 WHIP over a season and a half before leaving as a free agent after the 1998 season.

July 31, 1997: Mark McGwire Traded to St. Louis

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    Oakland Got: RHP Eric Ludwick, RHP T.J. Mathews, RHP Blake Stein

    Oakland knew that it wasn't going to be able to re-sign McGwire, a free agent, after the season, so the A's looked to move him for the best possible package they could get.

    That this was the best package available is pretty scary.

    Eric Ludwick appeared in six games for the A's, going 1-4 with a 8.25 ERA and 2.00 WHIP before being traded to Florida in the offseason for Kurt Abbott. 

    Blake Stein would fare a bit better than Ludwick, going 5-9 with a 6.60 ERA and 1.67 WHIP in 25 games over parts of two seasons with Oakland before being packaged along with Jeff D'Amico and Brad Rigby at the deadline in 1999 to acquire Kevin Appier from Kansas City.

    T.J. Mathews was the most successful of them all, spending nearly five years with the A's, finishing with a 24-15 record, 4.78 ERA and 1.44 WHIP before being released by the club halfway through the 2001 campaign.


    St. Louis Got: 1B Mark McGwire

    Sure, Mark McGwire would go on to become one of the faces of the steroid era in baseball, but that's irrelevant for our purposes.

    He'd hit 24 home runs in 51 games after the trade for the Cardinals and followed that up with his dramatic (it was at the time) race with Chicago's Sammy Sosa in 1998 to not only break Roger Maris' single-season home run record of 61, but to see who would be the first to hit 70 home runs.

    McGwire would appear in three All-Star Games as a Cardinal, hitting .270 with 220 home runs and 473 RBI in parts of five seasons with the club. He'd win a World Series title with the club in 2011 as the team's hitting coach.

July 26, 2000: Curt Schilling Traded to Arizona

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    Arizona Got: SP Curt Schilling

    Curt Schilling was just OK for the Diamondbacks after the trade, going 5-6 with a 3.69 ERA in 13 starts down the stretch in 2000, but the best was yet to come.

    He'd go 22-6 with a 2.98 ERA during the regular season in 2001, combining with Randy Johnson to win 43 games as the team went 92-70 and took home the franchise's first World Series title, with Schilling going 4-0 in six postseason starts.

    Schilling was equally as dominant in 2002, going 23-7 with a 3.23 ERA and NL-best 0.99 WHIP, once again pairing with the Big Unit to win 47 games, but the D-Backs couldn't get past St. Louis in the NLDS to defend their World Series crown.

    After an injury-filled 2003 campaign, Arizona broke up the band, shipping Schilling to Boston for a package that included RHP Casey Fossum and LHPs Jorge De La Rosa and Brandon Lyon.

    While his time in Arizona was relatively short, it was certainly productive: two All-Star appearances, two second-place finishes in the NL Cy Young Award voting (losing to Johnson both times) and, of course, a World Series ring.


    Philadelphia Got: LHP Omar Daal, RHP Nelson Figueroa, 1B Travis Lee and RHP Vicente Padilla

    On paper, this wasn't a bad haul for the Phillies.

    It was only two years earlier that Travis Lee had finished third in the NL Rookie of the Year voting, but he had slumped since then and seemed like a player who only needed a change of scenery to get himself back on track.

    While he wasn't terrible, hitting .258 with 34 home runs, 174 RBI and a .745 OPS in parts of three seasons with the Phillies, he never lived up to expectations and the team let him walk as a free agent following the 2002 season.

    Nelson Figueroa appeared in 19 games for the Phillies in 2001, going 4-5 with a 3.94 ERA and 1.48 WHIP before the club lost him on waivers to Milwaukee at the beginning of 2002.

    Omar Daal was slightly more successful than Figueroa, winning 15 games over two years (13 of them in 2001) before he too found himself elsewhere, traded to Los Angeles for Jesus Cordero and Eric Junge in November 2001.

    Vincente Padilla ultimately wound up as the only worthwhile return for the Phillies, going 49-49 with a 3.98 ERA and 1.34 WHIP, representing the club as an All-Star in 2002.

July 30, 2004: Scott Kazmir Traded to Tampa Bay

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    New York Got: RHP Bartolome Fortunato, RHP Victor Zambrano

    To be fair to the Mets, Scott Kazmir hasn't exactly had a stellar, injury-free career since he was traded from New York to Tampa Bay. But what he did in one season with the Rays exceeds the return that the Amazin's got for their former top prospect.

    Bartolome Fortunato threw a grand total of 21.2 innings for the Mets over parts of two years, pitching to a 7.06 ERA and 1.66 WHIP before he was released in 2006. He was undefeated, however, going 2-0, so at least he's got that to hang his hat on.

    Victor Zambrano, the key piece in the deal for New York, wound up having far more severe elbow issues than the Mets realized, managing to toss only 201.2 innings for the club over parts of three years. All but 45.1 of them came in 2005, when he went 7-12 with a 4.17 ERA.

    The club let him walk as a free agent after the 2006 season, finishing his Mets career 10-14 with a 4.42 ERA and 1.49 WHIP.


    Tampa Bay Got: LHP Scott Kazmir

    Injuries ultimately derailed Scott Kazmir's career until recently, but he established himself as one of the game's top young arms upon his arrival in Tampa Bay.

    From 2005 to 2008, Kazmir went 45-34 with a 3.51 ERA and 1.35 WHIP, making a pair of All-Star appearances and leading the American League with 239 strikeouts in 2007.

    He remained valuable to the Rays even after he lost his stuff in 2008, with the club able to flip him to the Los Angeles Angels for a package that bought back left-handed pitcher Alex Torres and super-utility man Sean Rodriguez, who remains a fixture in Tampa Bay today.

July 26, 2006: Shin-Soo Choo Traded to Cleveland

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    Cleveland Got: OF Shin-Soo Choo and LHP Shawn Nottingham

    For the second time in just about a month, Cleveland general manager Mark Shapiro absolutely fleeced the Seattle Mariners in a deal. First, he traded Eduardo Perez for Asdrubal Cabrera, following that move up with the acquisition of Shin-Soo Choo.

    While Shawn Nottingham never reached the major leagues, Choo did and quickly became one of the more underrated players in baseball.

    He could hit for average and for power, caused problems with his speed and showed an innate ability to get on base pretty much whenever he wanted, as evidenced by his .383 on-base percentage while wearing an Indians uniform.

    While he never reached an All-Star Game during his stay with the Indians, he hit .292 with 83 home runs, 85 stolen bases and a .853 OPS over seven seasons before being traded to Cincinnati as part of a three-team deal that brought Trevor Bauer back to Cleveland.


    Seattle Got: 1B/OF Ben Broussard and Cash

    After averaging 17 home runs and 68 RBI a year over his first three full seasons in the big leagues, the Seattle Mariners looked at Ben Broussard as a powerful addition to their lineup, someone who would serve as the team's designated hitter against right-handed batters.

    "I've always like Ben Broussard," Mariners manager Mike Hargrove told's Corey Brock shortly after the trade was announced. "I've always liked the way he's swung the bat. He brings some pop from that side and drives the ball."

    That pop didn't translate well to Safeco Field, as Broussard would hit only 15 home runs over parts of two seasons with the Mariners before being traded to Texas in December 2007 for Tug Hulett.

July 31, 2007: Mark Teixeira Traded to Atlanta

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    Atlanta Got: LHP Ron Mahay, 1B Mark Teixeira

    The Braves went all in at the deadline in 2007, trading a large chunk of their best young talent to Texas for Ron Mahay and Mark Teixeira.

    Mahay helped to solidify Atlanta's bullpen, pitching to a 2.25 ERA and 1.25 WHIP in 30 relief appearances, while Teixeira hit .317 with 17 home runs, 56 RBI and a 1.020 OPS in 54 games. But their arrivals weren't enough to propel Atlanta into the postseason, and Mahay walked as a free agent after the season.

    Entering the last year of his contract in 2008, Teixeira remained productive, hitting .283 with 20 home runs, 78 RBI and a .902 OPS. But the Braves couldn't afford to re-sign him, so they shipped him to Los Angeles at the deadline for right-handed pitcher Tyler Marek and first base prospect Casey Kotchman.

    While both players were successful during their time with the Braves, neither one was worth what it cost to acquire them.


    Texas Got: SS Elvis Andrus, RHP Neftali Feliz, LHP Matt Harrison, C Jarrod Saltalamacchia

    While Mahay and Teixeira are ancient history in Atlanta, only Jarrod Saltalamacchia is gone from the scene in Texas.

    Granted, Neftali Feliz and Matt Harrison have dealt with injuries—and Harrison's career may be over, even after he underwent spinal fusion surgery in June—but even if Elvis Andrus and Feliz are all the Rangers have left from this deal, the scales are still tipped heavily in their favor.

    Those three all played huge roles in Texas' recent success, including the team's two consecutive trips to the World Series in 2010 and 2011, and both Andrus and Feliz are sure to be a part of the team's future success, once it can get its roster healthy after an injury-filled 2014 campaign.

July 24, 2009: Matt Holliday Traded to St. Louis

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    Oakland Got: RHP Clayton Mortensen, 1B Shane Peterson and 1B/3B Brett Wallace

    Back when this trade went down, ESPN's Keith Law wrote the following (subscription required):

    The trade between the Cardinals and A's involving Matt Holliday looks like a win for both teams -- Oakland gets a strong troika of prospects that's better than what it gave to Colorado for Holliday seven months ago, while St. Louis gets a much-needed offensive boost that should greatly improve its chances of making the playoffs.

    He was right about one thing—Holliday helped the Cardinals' chances of appearing in the playoffs substantially.

    Brett Wallace never appeared in a game for Oakland and was traded to Toronto five months later for Michael Taylor, while Clayton Mortensen made seven starts over parts of two seasons for the A's, going 2-4 with a 7.22 ERA and 1.69 WHIP before he was traded to Colorado for minor league pitcher Ethan Hollingsworth in January 2011.

    Shane Peterson is the only part of the package that remains in Oakland's system and is currently putting up big numbers at Triple-A Sacramento (.324 BA, 8 HR, 70 RBI, .861 OPS), but he's 26 years old and mustered only one hit in seven major league at-bats in 2013. He's no longer a prospect at this point.


    St. Louis Got: OF Matt Holliday

    Matt Holliday has been a major part of St. Louis' recent success and, despite the fact that he's having a down year, remains a key piece of the puzzle for manager Mike Matheny.

    Over parts of six seasons with the Cardinals, Holliday has hit .301 with 122 home runs, 482 RBI and a .894 OPS, appearing in three All-Star Games.

July 29, 2009: Cliff Lee Traded to Philadelphia

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    Cleveland Got: RHP Carlos Carrasco, UTIL Jason Donald, RHP Jason Knapp and C Lou Marson

    When Indians general manager Mark Shapiro explained his thought process behind this trade, it made sense. Per ESPN's Jayson Stark:

    At the root of this deal was balancing the conviction of our ability to compete in 2010 with the opportunity to impact the team's construction for years to come. Without the sense of confidence in the team's ultimate competitiveness, we acted aggressively to add players that will impact the organization in 2010 and beyond.

    Unfortunately for the Indians, things didn't work out quite as they planned.

    Carlos Carrasco never developed into the front-of-the-rotation arm that they envisioned, and he currently finds himself serving as the team's long reliever. 

    Jason Donald spent parts of three years with the Tribe, hitting .257 with a .672 OPS while playing all over the field, but he was traded to Cincinnati in 2012 and hasn't seen the major leagues since.

    Lou Marson was a capable backup catcher for Cleveland for five years, but he didn't hit (.219 BA, .609 OPS) and the team let him walk as a free agent in 2013.

    Jason Knapp never made it past Single-A in the organization and was out of baseball for three years before resurfacing with Texas this season.

    Interestingly enough, the Indians could have gotten outfielders Domonic Brown or Michael Taylor in the deal, according to The Plain Dealer's Paul Hoynes, but they would have had to pass on either Knapp or Marson.

    Had they landed Brown, perhaps this deal wouldn't look quite as lopsided as it does.


    Philadelphia Got: OF Ben Francisco and LHP Cliff Lee

    While the Phillies might be trying to unload Cliff Lee at this year's deadline, there's no question that they'd make this trade over and over again if the opportunity presented itself.

    Ben Francisco spent parts of three years in Philadelphia, two as a fourth outfielder, but he came through in the clutch for the club when it counted.

    With no score in the top of the seventh inning in Game 3 of the 2011 NLDS against St. Louis, Francisco pinch-hit for Cole Hamels and smacked a three-run home run that ultimately won the game.

    Cliff Lee would go 7-4 down the stretch for the Phillies in 2009 and was a major reason why the club advanced to the World Series, where they eventually lost to the New York Yankees. In five postseason starts, Lee went 4-0 with a 1.56 ERA while holding opponents to a paltry .450 OPS.

    While the Phillies ultimately traded him to Seattle after the season, Lee found his way back to Philadelphia as a free agent in 2011.