The Most Brutal Blockbuster MLB Trade Deadline Fails Since 2000

Joel Reuter@JoelReuterBRFeatured ColumnistJuly 15, 2019

The Most Brutal Blockbuster MLB Trade Deadline Fails Since 2000

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    Ross D. Franklin/Associated Press

    There's undeniable risk when it comes to pulling the trigger on a blockbuster deal at the trade deadline.

    Case in point, even after he helped them win a World Series, fans around the league still question the Chicago Cubs' decision to trade Gleyber Torres for two months of flamethrowing closer Aroldis Chapman.

    Ahead, we set out to find the most regrettable deadline deals since 2000.

    First, a few stipulations:

    • July trades only: Trades had to occur during the month of July to be included. That notably excluded the deal that sent Bartolo Colon to the Montreal Expos in exchange for Cliff Lee, Grady Sizemore and Brandon Phillips on June 27, 2002.
    • Time to digest: No trades from 2017 or 2018 were included in the rankings, although some appear among the honorable mentions. It's simply too soon to tell how trades from the past two years will ultimately play out. The Tampa Bay Rays acquiring Austin Meadows and Tyler Glasnow in exchange for Chris Archer last summer sure seems destined for this list, though.

    With that, let's kick things off with some honorable mentions before diving into the 10 most brutal blockbuster trade fails since 2000.

    The trades are ranked based on a combination of lopsidedness and the production and impact the key player in each deal had on his team's success, particularly in the postseason.

Honorable Mentions

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    Melvin Mora
    Melvin MoraJERRY S. MENDOZA/Associated Press
    • 7/28/2000: BAL acquired 3B Melvin Mora, OF Mike Kinkade, RHP Leslie Brea, RHP Pat Gorman from NYM for SS Mike Bordick
    • 7/29/2000: PIT acquired SS Jack Wilson from STL for LHP Jason Christiansen
    • 7/30/2001 SF acquired RHP Jason Schmidt, OF John Vander Wal from PIT for RHP Ryan Vogelsong, OF Armando Rios
    • 7/30/2003: CIN acquired RHP Aaron Harang, RHP Joe Valentine, RHP Jeff Bruksch from OAK for OF Jose Guillen
    • 7/31/2003: PIT acquired 2B Freddy Sanchez, LHP Mike Gonzalez, cash from BOS for RHP Jeff Suppan, RHP Brandon Lyon, RHP Anastacio Martinez
    • 7/30/2004: TB acquired LHP Scott Kazmir, RHP Jose Diaz from NYM for RHP Victor Zambrano, RHP Bartolome Fortunato
    • 7/18/2006: SD acquired RHP Mike Adams from CLE for RHP Brian Sikorski
    • 7/28/2007: TB acquired RHP Grant Balfour from MIL for RHP Seth McClung
    • 7/26/2008: CLE acquired Carlos Santana, RHP Jon Meloan from LAD for 3B Casey Blake
    • 7/30/2009: PIT acquired 2B Josh Harrison, RHP Kevin Hart, RHP Jose Ascanio from CHC for LHP Tom Gorzelanny, LHP John Grabow
    • 7/29/2010: WAS acquired C Wilson Ramos, LHP Joe Testa from MIN for RHP Matt Capps
    • 7/30/2010: WAS acquired RHP Tanner Roark, RHP Ryan Tatusko from TEX for IF Cristian Guzman
    • 7/30/2011: DET acquired RHP Doug Fister, RHP David Pauley from SEA for LHP Charlie Furbush, OF Casper Wells, 3B Francisco Martinez, RHP Chance Ruffin
    • 7/30/2011: BAL acquired 1B Chris DavisRHP Tommy Hunter from TEX for RHP Koji Uehara
    • 7/21/2012: HOU acquired RHP Chris Devenski, LHP Blair Walters, RHP Matt Heidenreich from CWS for RHP Brett Myers
    • 7/25/2012: LAD acquired SS Hanley Ramirez, LHP Randy Choate from MIA for RHP Nathan Eovaldi, RHP Scott McGough
    • 7/28/2012: MIN acquired 3B Eduardo Escobar, LHP Pedro Hernandez from CWS for LHP Francisco Liriano
    • 7/31/2012: SF acquired RF Hunter Pence from PHI for OF Nate Schierholtz, C Tommy Joseph, RHP Seth Rosin
    • 7/5/2014: CHC acquired SS Addison Russell, OF Billy McKinney, RHP Dan Straily, cash from OAK for SP Jeff Samardzija, SP Jason Hammel
    • 7/31/2014: ARI acquired OF Mitch HanigerLHP Anthony Banda from MIL for OF Gerardo Parra
    • 7/30/2015: MIL acquired LHP Josh Hader, OF Domingo Santana, OF Brett Phillips, RHP Adrian Houser from HOU for CF Carlos Gomez, SP Mike Fiers, cash
    • 7/30/2015: CIN acquired OF Adam Duvall, RHP Keury Mella from SF for RHP Mike Leake
    • 7/31/2015: MIL acquired RHP Zach Davies from BAL for OF Gerardo Parra
    • 7/30/2016: PIT acquired LHP Felipe Vazquez, LHP Taylor Hearn from WAS for RHP Mark Melancon
    • 7/29/2018: NYY acquired 1B Luke Voit, international bonus money from STL for RHP Giovanny Gallegos, LHP Chasen Shreve
    • 7/31/2018: TB acquired RHP Tyler GlasnowOF Austin Meadows, RHP Shane Baz from PIT for RHP Chris Archer

10. Texas Rangers Acquire Nelson Cruz

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    LM Otero/Associated Press

    Date: July 28, 2006

    To TEX: LF Carlos Lee, OF Nelson Cruz

    To MIL: OF Kevin Mench, RHP Francisco Cordero, OF Laynce Nix, LHP Julian Cordero

    The main outline of this trade made perfect sense.

    A contending Texas Rangers team picked one of the most prolific sluggers in the league, Carlos Lee, as a rental bat for its playoff push.

    A non-contending Milwaukee Brewers team found a replacement for him with an additional year of team control in Kevin Mench and bought low on closer Francisco Cordero in a down year.

    So why in the world did the Brewers also agree to include Nelson Cruz?

    Surely, the Rangers would not have walked away over the inclusion of a Triple-A outfielder who was nowhere near leaguewide top 100 lists.

    After spending two seasons bouncing between Triple-A and the majors, everything clicked for Cruz in 2009 when he posted a 117 OPS+ with 33 home runs and 20 steals to earn a spot on the AL All-Star team.

    All told, he spent parts of eight seasons in Texas, slugging 157 home runs while posting a 114 OPS+. He also hit .270/.331/.689 with 14 home runs and 27 RBI in 33 postseason games to help the Rangers win back-to-back AL pennants in 2010 and 2011.

9. Cleveland Indians Acquire Shin-Soo Choo

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    Paul Sancya/Associated Press

    Date: July 26, 2006

    To CLE: RF Shin-Soo Choo, LHP Shawn Nottingham

    To SEA: 1B Ben Broussard, cash

    Despite a 49-52 record, the Seattle Mariners were just three games back in the AL West on July 26 when they swung a deal to acquire Ben Broussard from the Cleveland Indians.

    The 29-year-old was hitting a robust .321/.361/.519 with 13 home runs in 288 plate appearances at the time of the trade, and the Mariners immediately installed him as their primary DH and No. 6 hitter.

    While it looked like a great addition at the time, he batted just .238/.282/.427 with eight home runs in 56 games the rest of the way and the Mariners ended up finishing in the AL West cellar.

    The price they paid for those two middling months was steep.

    Outfielder Shin-Soo Choo began the 2006 season as the No. 7 prospect in the Seattle farm system, per Baseball America, and the 23-year-old was hitting .323/.394/.499 with 37 extra-base hits and 26 steals with Triple-A Tacoma at the time of the trade.

    The Indians sent him straight to the MLB roster and he batted .295/.373/.473 with 17 extra-base hits in 45 games following the trade. After an injury-plagued 2007 season, he emerged as a staple in the Cleveland outfield, posting a combined 134 OPS+ in his seven seasons with the team.

    This trade proved to be the gift that kept on giving when Choo was traded to the Cincinnati Reds prior to the 2013 season in a three-team, nine-player trade that brought both Trevor Bauer and Bryan Shaw to the Indians.

8. Tampa Bay Rays Acquire Ben Zobrist

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    Chris O'Meara/Associated Press

    Date: July 12, 2006

    To TB: UT Ben Zobrist, RHP Mitch Talbot 

    To HOU: 3B/RF Aubrey Huff

    With Morgan Ensberg scuffling on the heels of a breakout 2005 season, the Houston Astros landed one of the market's biggest rental bats in Aubrey Huff to man third base. He also saw time in right field once Ensberg returned to the starting lineup.

    Huff had a 108 OPS+ with eight home runs in 63 games at the time of the trade, and he posted a nearly identical 107 OPS+ with 13 home runs in 68 games in Houston, so he lived up to expectations. However, the Astros missed the playoffs and Huff signed with the Baltimore Orioles in free agency.

    In exchange for one of the most productive hitters in the brief history of their franchise, the Tampa Bay Rays acquired Ben Zobrist, who had begun the 2006 season as the No. 16 prospect in the Houston farm system.

    The 25-year-old was hitting .327/.434/.473 with 34 extra-base hits and more walks (55) than strikeouts (46) in Double-A at the time of the trade. The Rays immediately promoted him to Triple-A, and he made his MLB debut on Aug. 1, but it was not until the 2009 season that he established himself at the big league level.

    He hit .297/.405/.543 with 28 doubles, 27 home runs and 91 RBI to finish eighth in AL MVP voting during his breakout 2009 campaign, playing all over the diamond in the process.

    Zobrist went on to spend nine seasons in Tampa Bay, posting a 117 OPS+ and 36.0 WAR before he was traded to the Oakland Athletics.

7. Oakland Athletics Acquire Josh Donaldson

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    Eric Risberg/Associated Press

    Date: July 8, 2008

    To OAK: 3B Josh Donaldson, OF Matt Murton, RHP Sean Gallagher, OF Eric Patterson

    To CHC: RHP Rich Harden, RHP Chad Gaudin

    This move paid immediate dividends for the Chicago Cubs.

    Rich Harden went 5-1 with a 1.77 ERA and 89 strikeouts in 71 innings over 12 starts to help a contending Chicago Cubs team reach the postseason. He followed that up with a 4.09 ERA and 171 strikeouts in 141 innings the following season and then walked in free agency.

    Still, it looked like a solid clear win for the North Siders.

    Matt Murton, Sean Gallagher and Eric Patterson were all MLB-ready players expected to contribute immediately for the Athletics. Instead, all three were playing elsewhere by 2010 after posting a combined minus-2.2 WAR in Oakland.

    It was not until 2013 that this one shifted dramatically into the Oakland Athletics win column.

    The only prospect in the deal was then-catcher Josh Donaldson, who had been a supplemental first-round pick in 2007 and ranked as the No. 7 prospect in the Cubs system prior to 2008.

    After a middling performance in his first extended MLB action in 2012, he came out of nowhere to hit .301/.384/.499 with 24 home runs and 93 RBI to finish fourth in AL MVP voting during his age-27 season.

    That proved to be just the beginning. He has now piled up 41.3 WAR over the course of his nine-year MLB career, posting a 137 OPS+ with 203 home runs and winning AL MVP honors in 2015.

6. Texas Rangers Acquire Michael Young

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    Ezra Shaw/Getty Images

    Date: July 19, 2000

    To TEX: SS Michael Young, RHP Darwin Cubillan

    To TOR: RHP Esteban Loaiza

    In a strange twist of events, the struggles of future Cy Young winners Roy Halladay and Chris Carpenter at the onset of their careers with the Toronto Blue Jays are a big reason for one of the most lopsided trades in recent memory.

    Desperately seeking rotation help, the Blue Jays acquired Esteban Loaiza—who was still a few years removed from his breakout season with the Chicago White Soxfrom the Texas Rangers.

    The 28-year-old posted a 3.62 ERA in 14 starts down the stretch and he was a fixture in the Toronto rotation the next two seasons, but the Blue Jays settled for three straight third-place finishes in the AL East during that span.

    Michael Young, the No. 4 prospect in the Toronto system at the time, went the other way in the deal.

    While he stepped into the starting second base job in 2001, it took him some time to get settled in at the MLB level. It was not until the 2003 season that he broke out, hitting .306/.339/.446 with 204 hits.

    That would be the first of six 200-hit seasons and the first of seven seasons in which he hit .300 or better, including a .331 average in 2005 that won him the AL batting title.

    In 13 seasons with the Rangers, Young made seven trips to the All-Star Game and hit .301/.347/.444 while racking up 2,230 hits and 25.9 WAR.

5. Chicago Cubs Acquire Aramis Ramirez

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    Gene J. Puskar/Associated Press

    Date: July 23, 2003

    To CHC: 3B Aramis Ramirez, CF Kenny Lofton, cash

    To PIT: 2B Bobby Hill, RHP Matt Bruback, IF Jose Hernandez

    Let's start with what the Pittsburgh Pirates received in this trade.

    Bobby Hill exhausted his rookie status in 2002, but he was the No. 48 prospect in baseball at the start of the 2002 season. That said, he was 25 years old at the time of the trade and offered little upside. He posted an 82 OPS+ and 0.2 WAR as the team's starting second baseman the following season and spent one more year in the majors.

    Matt Bruback was the No. 18 prospect in the Cubs system and he had a 3.96 ERA with 6.5 K/9 in 125 innings at Triple-A at the time of the trade. He was claimed off waivers by the San Diego Padres less than a month later.

    Jose Hernandez was a 33-year-old infielder who hit .223/.282/.326 as a placeholder at third base before he was released on Oct. 1.

    That might have been a reasonable return package for veteran rental Kenny Lofton, who went on to hit .327/.381/.471 with 12 steals and 39 runs scored in 56 games with the Cubs, helping ease the loss of center fielder Corey Patterson.

    It's unfathomable that the Pirates couldn't get more for Aramis Ramirez.

    The 25-year-old had signed a team-friendly three-year, $9.5 million deal prior to the 2002 season and still had a year of arbitration remaining on the back end of that, making him an extremely cheap option through 2005. 

    He already had a 34-homer, 112-RBI season under his belt in 2001, and he was hitting a respectable .280/.330/.448 with 12 home runs at the time of the trade.

    Ramirez went on to spend nine seasons with the Cubs, posting a 126 OPS+ with 239 home runs and 806 RBI, making a pair of All-Star teams and posting 29.9 WAR.

4. Chicago Cubs Acquire Kyle Hendricks

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    Jonathan Daniel/Getty Images

    Date: July 31, 2012

    To TEX: RHP Ryan Dempster

    To CHC: RHP Kyle Hendricks, 3B Christian Villanueva

    The Los Angeles Dodgers' refusal to include top pitching prospect Allen Webster in a deal for rental starter Ryan Dempster may well have altered the course of Chicago Cubs history.

    With 10-and-5 veto power, Dempster made it clear Los Angeles was his preferred destination in trade talks. However, the Webster hurdle proved insurmountable, and he eventually accepted a trade to the Texas Rangers. The 35-year-old had a 2.25 ERA in 16 starts at the time of the trade but struggled to a 5.09 ERA in 12 starts with the Rangers before leaving in free agency.

    Third baseman Christian Villanueva was the biggest prospect piece at the time of the trade, checking in as the No. 8 prospect in the Texas system and the No. 100 prospect in baseball at the start of the 2012 season.

    Meanwhile, soft-tossing Kyle Hendricks was not even ranked among the team's top 30 prospects. However, he had a 2.82 ERA and a 112-to-15 strikeout-to-walk ratio in 130.2 innings at High-A Myrtle Beach prior to the trade, and the Cubs front office took notice.

    Four years after the trade, Hendricks carved out his place in Cubs lore. He threw a gem in Game 6 of the 2016 NLCS (7.1 IP, 2 H, 0 ER) and also earned the start in Game 7 of the World Series (4.2 IP, 4 H, 1 ER)—toeing the rubber in arguably the two biggest games in recent franchise history.

    All told, he's gone 59-40 with a 3.11 ERA, 1.12 WHIP and 18.5 WAR in six seasons in the majors, and a four-year, $55.5 million extension signed during the offseason will keep him under contract through at least 2023.

3. Texas Rangers Acquire Elvis Andrus, Neftali Feliz, Matt Harrison

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    Kevork Djansezian/Getty Images

    Date: July 31, 2007

    To TEX: SS Elvis Andrus, RHP Neftali Feliz, LHP Matt Harrison, C Jarrod Saltalamacchia, LHP Beau Jones

    To ATL: 1B Mark Teixeira, LHP Ron Mahay

    If the Atlanta Braves had won the World Series in 2007, this trade would have gone down as one of the best in franchise history. Facing a 3.5-game deficit in the NL East on deadline day, the Braves landed the biggest bat on the market, and Mark Teixeira hit a gaudy .317/.404/.615 with 17 home runs and 56 RBI in 54 games following the trade.

    Instead, it was a fantastic individual performance that went for naught.

    Atlanta went 28-27 the rest of the way to miss the postseason, and Teixeira was flipped by a sub-.500 Braves team at the following deadline for Casey Kotchman and Stephen Marek.

    That proved to be pennies on the dollar for what they paid to acquire him, which was an astronomically steep price. Here's a quick rundown of where the players included in the package ranked in the Atlanta system and leaguewide:

    • C Jarrod Saltalamacchia: No. 1 ATL prospect, No. 36 MLB prospect
    • SS Elvis Andrus: No. 2 ATL prospect, No. 65 MLB prospect
    • LHP Matt Harrison: No. 3 ATL prospect, No. 90 MLB prospect
    • LHP Beau Jones: No. 14 ATL prospect
    • RHP Neftali Feliz: No. 16 ATL prospect


    Elvis Andrus, Matt Harrison and Neftali Feliz were all key members of the Rangers teams that won back-to-back AL pennants in 2010 and 2011. On the flip side, it was no small coincidence this trade corresponded with a long rebuilding period for the Braves, one from which they are just now emerging.

2. Chicago Cubs Acquire Jake Arrieta

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    John Minchillo/Associated Press

    Date: July 2, 2013

    To CHC: RHP Jake Arrieta, RHP Pedro Strop, cash

    To BAL: RHP Scott Feldman, C Steve Clevenger

    Chicago Cubs team president Theo Epstein said it perfectly while talking with reporters in February 2018: "None of us have rings without Jake Arrieta."

    A fifth-round pick by the Baltimore Orioles in 2007, Arrieta was ranked as high as the No. 67 prospect in baseball prior to the 2009 season. He was never able to break through with the O's, though, posting a 5.46 ERA and 1.47 WHIP in 358 innings over parts of four seasons with the big league club.

    The Cubs front office saw a chance to unlock his potential by going back to basics with his mechanics, and he was acquired in the early stages of the team's rebuilding efforts.

    Veteran Scott Feldman went the other way after signing a one-year, $6 million deal during the offseason and posting a 3.46 ERA and 1.14 WHIP in 15 starts with the Cubs. He had a 4.27 ERA in 15 starts with the O's, but they failed to make the playoffs, and he bolted in free agency.

    Meanwhile, Arrieta posted a 2.53 ERA and 0.99 WHIP in 156.2 innings during his first full season in Chicago, and he won NL Cy Young honors the following year on the strength of a brilliant second half that saw him go 12-1 with a 0.75 ERA and 0.73 WHIP in 15 starts.

    All told, he pitched to a 2.73 ERA and 1.03 WHIP in 128 starts over five seasons in Chicago, and he added a 3.08 ERA and 1.08 WHIP in nine postseason starts, including two wins and a 2.38 ERA in the 2016 World Series.

    Simply acquiring reliever Pedro Strop would have been enough for this trade to land as an honorable mention. In seven seasons on the North Side, he's used his wicked slider to post a 2.78 ERA and 10.2 K/9 with 28 saves and 117 holds in 386 appearances.

    Again, the Cubs don't win a World Series without this trade.

1. Cleveland Indians Acquire Corey Kluber

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    Mark Brown/Getty Images

    Date: July 31, 2010

    To CLE: RHP Corey Kluber

    To STL: RHP Jake Westbrook, LHP Nick Greenwood

    To SD: OF Ryan Ludwick

    At the time, this trade made headlines as a Ryan Ludwick-for-Jake Westbrook swap.

    Ludwick had a .827 OPS with 11 home runs at the time of the trade. His production dipped following the deal, though, and he was sent to the Pittsburgh Pirates for cash considerations exactly one year later.

    Westbrook had a 4.65 ERA in 21 starts leading up to the deadline. He posted a solid 3.48 ERA in 12 starts in St. Louis, signed a new two-year, $16.5 million deal with the team during the offseason and helped the team to a World Series title in 2011.

    For posterity, this will be known as the Corey Kluber trade.

    While he was unranked among the San Diego Padres' top 30 prospects at the start of the 2010 season, Kluber impressed at the Double-A level, posting a 3.45 ERA with 136 strikeouts in 122.2 innings.

    After an inauspicious debut in 2011 and a 5.14 ERA in 12 starts in 2012, he became a regular in the 2013 rotation with a 3.85 ERA, 1.26 WHIP and 136 strikeouts in 147.1 innings.

    The following year, he was the AL Cy Young winner, rapidly emerging as one of baseball's elite pitchers. He added another Cy Young trophy to his mantle in 2017, and in nine seasons with the Indians, he's gone 98-58 with a 3.16 ERA, 1.09 WHIP and 1,461 strikeouts in 1,341.2 innings for 33.2 WAR.

    He was also instrumental in the team reaching the World Series in 2016, posting a dominant 1.83 ERA over six postseason starts.

    So while the Jake Arrieta trade may have had a bigger impact on the Cubs organization, the Kluber deal is an easy pick for the No. 1 spot in terms of sheer lopsidedness.


    All stats courtesy of Baseball Reference and FanGraphs, unless otherwise noted.