The 15 worst MLB trade deadline deals in history, ranked
The risk/reward nature of the deals that happen before MLB’s annual trading deadline are exciting, both for the fans of the teams involved and the front-office types who make them.
But for every fan base and GM thrilled with the outcome, there’s another group wondering how in the world something could have gone so very wrong. We’re looking at this group of memorable deadline deals from that perspective.
Parameters have to be set somewhere (we did every team’s worst in-season trade a few years ago), so here are ours: For July, we’re only looking at deals made the last two weeks of July, before the traditional July 31 non-waiver deadline. You won’t see lopsided deals from early July (Jake Arrieta from Baltimore to Chicago, on July 2, 2013) or June (Bartolo Colon for Cliff Lee, Grady Sizemore and Brandon Phillips on June 27, 2002) or May (when Mike Piazza was dealt twice in about a week in May 1998).
We will include deals made during the now-defunct August waiver period, because there’s often that same desperate-to-contend-so-let’s-just trade-the-prospect feel that leads to bad decisions. Make sense?
Oh, and we’re still waiting for more information on a couple of recent deals that might eventually belong on this list. Here are two from 2018: Austin Meadows and Tyler Glasnow looked great immediately for Tampa Bay after they were traded by Pittsburgh for Chris Archer, who has often been ineffective or injured for the Pirates. Luke Voit has been amazing for the Yankees after the Cardinals shipped him to NYC for Chasen Shreve and Giovanny Gallegos (who has been stellar himself).
Now, let’s get started.
The trade: July 28, 1995. David Cone to the Yankees for Marty Janzen, Mike Gordon and Jason Jarvis
Why it’s here: Remember, the Yankees hadn’t made the postseason in more than a decade when Cone arrived in the summer of 1995. They made the playoffs that year — the Yankees went 9-4 in his 13 starts, which helped — and immediately launched into yet another dynasty run for the franchise. It wasn’t all about Cone, of course, but he was one of a handful of veterans the club brought in that teamed with the young, home-grown core to make the Yankees a powerhouse again. In his six years with the Yankees, Cone had a 3.91 ERA in 145 regular-season games (one relief appearance) and a 3.86 ERA in 77 postseason innings.
The trade: July 26, 1993. Andy Ashby, Brad Ausmus and Doug Bochtler to the Padres for Bruce Hurst and Greg Harris
Why it’s here: The Rockies, who were 26 games under .500 when they made this deal midway through their inaugural season, thought they were getting two reliable veteran starters, but Harris lasted just 42 games (32 starts) in Colorado before he was released with a 6.60 ERA over parts of two seasons. And Hurst made just three starts with the Rockies before he left as a free agent. Ashby developed into an outstanding starter for the Padres (he had a 3.49 ERA in 173 starts from 1994 to 1999) and Ausmus made his MLB debut soon after the trade, embarking on what turned into an 18-year big-league career.
The trade: Aug. 29, 1996. David Ortiz (then Arias) to the Twins for Dave Hollins
Why it’s here: Everyone knows the Twins gave up on Ortiz too soon (Red Sox fans are thankful), but how many people remember that he started in the Seattle organization? The Mariners, looking for a playoff boost, traded for Dave Hollins in late August, and Hollins hit .351 with 25 RBIs in 28 games for Seattle. Ortiz had just finished a successful season in Single-A ball, where he batted .322 with 18 homers as a 20-year-old first baseman. The Twins liked that, and two weeks after the Mariners acquired Hollins, they sent Ortiz to Minnesota as the player to be named later. Also, this would be higher on the list if the legend of Big Papi would have been established in Minnesota.
The trade: July 23, 2003. Aramis Ramirez and Kenny Lofton to the Cubs for Bobby Hill, Jose Hernandez and Matt Bruback
Why it’s here: This deal would have been bad enough if the Pirates had made the deal with an AL club. But for the Pirates to give Ramirez and Lofton to the Cubs — an NL Central rival — and for the Pittsburgh fans to have to watch the Cubs immediately benefit (2003 was the Year of Bartman, remember) was painful. Lofton only played that year in Chicago, but Ramirez hit 239 home runs in his nine years with the Cubs.
The trade, Part I: July 29, 1988. Red Sox sent Schilling and Brady Anderson to the Orioles for Mike Boddicker
The trade, Part II: July 26, 2000. Phillies sent Curt Schilling to the Diamondbacks for Travis Lee, Vicente Padilla, Omar Daal and Nelson Figueroa.
Why it’s here, Part I: On its own, this one might not make the cut because Mike Boddicker was a veteran reliable starting pitcher who was excellent in his two-plus seasons with the Red Sox (3.49 ERA in 83 games). But we know the pitcher Schilling became (mostly after he moved on from Baltimore) and Anderson was a mainstay in the Orioles’ outfield for more than a decade.
Why it’s here, Part II: This isn’t so much about the guys the Phillies got in return — they were fine, though not exceptional — but it’s about Schilling. He finished second in the NL Cy Young vote in 2001 and 2002, and then was second in the AL Cy Young vote in 2004. And at the time of this trade, the Phillies had only won one World Series title (1980) in franchise history, which dates to 1883. So, of course, Schilling helped lead the Diamondbacks to the World Series title in 2001 and the Red Sox to the World Series titles in 2004 and 2007.
The trade: July 18, 1993. Fred McGriff to the Braves for Melvin Nieves and two others
Why it’s here: McGriff had led the NL in home runs in 1992, but the Padres were in sell-now mode (they’d already shipped out Gary Sheffield). McGriff was still a couple of years from free agency, but they traded him to Atlanta for three players who never did much in a Padres uniform. McGriff, on the other hand, continued to do what McGriff did his whole career — hit home runs, play solid first base and be a good clubhouse influence. He was an All-Star three times in his four full seasons with the Braves and hit two World Series home runs as Atlanta took the 1995 crown.
The trade: July 28, 2006. Carlos Lee and Nelson Cruz to the Rangers for Francisco Cordero, Kevin Mench, Laynce Nix and Julian Cordero
Why it’s here: The goal of this trade was for the Brewers to get something for Lee, a veteran slugger who was destined for free agency and didn’t show any interest in re-upping with Milwaukee. That wasn’t the problem. The problem was including Cruz, then a minorleague outfielder with eight MLB games under his belt. You know what happened with that. It took a couple of years, but he developed into one of the best power hitters in the AL and was a huge part of the Rangers’ push to back-to-back World Series trips in 2010 and 2011. Since 2007, only one player — Albert Pujols with 409 — has hit more homers than Cruz, who has 406 in that span. Francisco Cordero excelled as Milwaukee’s closer, but only for a short time before he left as a free agent after the 2007 season. Neither Mench nor Nix did much at the plate for the Brewers.
The trade: July 21, 1988. Jay Buhner and two others to the Mariners for Ken Phelps.
Why it’s here: Yankees fans were not pleased with this move for years after it happened. Buhner had 30 home runs and more than 100 RBIs, he had a rocket for an arm, and fans wondered whether George Steinbrenner knew what in the hell he was doing. The Yankees’ baseball people, apparently, loved Ken Phelps’ bat. (Any excuse to link to that “Seinfeld” clip is a good excuse.) Really, though, it took a couple of years for Buhner to become a regular in Seattle, but he was an anchor in the lineup for those Ken Griffey Jr.-led teams that were so exciting to watch.
The trade: July 19, 2000. Michael Young to the Rangers for Esteban Loaiza
Why it’s here: How many people outside Toronto actually remember that Young, who was long the face of the Rangers’ franchise, was actually a Blue Jays’ farmhand? At the time of this deal, Young was a 23-year-old Double-A second baseman hitting .275, and Loaiza was a 28-year-old starter the Blue Jays wanted to make a playoff push. Even though Loaiza was solid (3.62 ERA in 14 starts), the Jays missed the postseason. Young became a starter in Texas by 2001, made seven All-Star teams with the Rangers, and finished his 13 years in Texas with a .301 batting average.
The trade: July 31, 2012. Kyle Hendricks and Christian Villanueva to the Cubs for Ryan Dempster
Why it’s here: The 35-year-old Dempster made a dozen starts for the Rangers in 2012, posting a 5.09 ERA; Texas finished a game back of the A’s in the AL West and lost the wild-card game to the Orioles. Hendricks, though? He’s been a mainstay in the Cubs’ rotation, posting a 3.16 ERA in 169 games (168 starts) since making his big league debut in 2014. Oh, and he had a 0.83 ERA in his final four starts of the 2016 postseason — two in the NLCS and two in the World Series — helping the Cubs break their mildly long WS title drought.
The trade: July 31, 2010. Padres trade Corey Kluber to the Indians as part of three-way trade with Cardinals, receive Ryan Ludwick
Why it’s here: The deal went like this: St. Louis sent Ludwick to the Padres. Cleveland sent Jake Westbrook to the Cardinals. San Diego sent minor league pitcher Kluber to the Indians and minor league pitcher Nick Greenwood to the Cardinals. The Padres got their bat, the Cardinals got their veteran starter and the Indians got a 24-year-old right-hander in Double-A with good, not great minor league numbers. Cleveland was the clear long-term winner of this deal. Westbrook was exactly what the Cardinals expected of him, but the club missed the 2010 postseason. The Padres reached 90 wins (their only 90-win season since 1998, fwiw), but missed October because they finished two games back of the NL West title and one game out of the wild-card spot. Ludwick hit .228 in his 160 games with San Diego before he was traded the next season. In one five-year span, starting in 2014, Kluber won two AL Cy Young awards and finished third two other times.
The trade: July 31, 2007. Elvis Andrus, Neftali Feliz, Matt Harrison, Jarrod Saltalamacchia and Beau Jones to the Rangers for Mark Teixeira and Ron Mahay
Why it’s here: Teixeira, who was a year away from free agency, was considered the missing slugger the Braves needed for their 2007 playoff push, but even though he was great (1.020 OPS, 17 homers in 54 games), Atlanta missed the postseason. The trade was a boon for the Rangers. Andrus has developed into a Texas franchise icon, and Feliz was a late-inning star during Texas’ run to both the 2010 and 2011 World Series. Harrison won 14 games in 2011 and 18 in 2012. Saltalamacchia was just beginning his 12-year career as a big league catcher. To make matters worse, when the Braves traded Teixeira a year later, all they got in return was Casey Kotchman and Stephen Marek. Yikes.
The trade: July 31, 1997. Trade Derek Lowe and Jason Varitek to the Red Sox for Heathcliff Slocumb
Why it’s here: The Mariners were in the midst of a playoff chase and needed bullpen help. The Red Sox, who were fumbling along in the 1997 standings, needed two players who would be part of a core group that would eventually win the 2004 World Series. So, win-win, right? Not quite. Slocumb had been a solid closer in 1995 (for the Phillies) and 1996 (for the Red Sox), but he was struggling in 1997, to the tune of a 5.79 ERA and five blown saves in 22 opportunities. Still, the Mariners agreed to send both Varitek and Lowe to Boston. It looked bad at the time, and it looked worse and worse as both Varitek and Lowe became Red Sox stalwarts, and then really bad when Boston ended its curse and won it all in 2004. Slocumb had a 4.97 ERA in 84 career appearances with the Mariners.
The trade: Aug. 12, 1987. John Smoltz to the Braves for Doyle Alexander
Why it’s here: Yep, we’re looking at this through the cruel lens of retrospect, which is not how the trade was viewed at the time. Smoltz was a 22nd-round pick who had struggled mightily at Double-A that season (5.68 ERA in 21 starts, with a 6.0 K/9 ratio) and struggled in three starts for Atlanta’s Triple-A squad after the deal (6.19 ERA). Alexander, a veteran starter, was exactly what Detroit needed — he went 9-0 with a 1.53 ERA the rest of the 1987 regular season. But Smoltz, of course, morphed into Hall of Famer John Smoltz during his 21-year career in the bigs, and Alexander, 36 at the time of the trade, was done after two more years in with Detroit.
The trade: Aug. 30, 1990. Jeff Bagwell to the Astros for Larry Andersen
Why it’s here: This is the type of deal that gives GMs nightmares as they’re trying to make postseason push acquisitions. Bagwell, who was born in Boston and had grown up a Red Sox fan, had just hit .333 in Double-A, but with very little power (four homers in 136 games), and the big club needed/wanted a veteran reliever to add to its bullpen. Anderson was perfect — he had a 1.23 ERA in 15 appearances and helped the Red Sox to the AL East title (they were swept in the ALCS by Oakland) — but Bagwell became, well, Bagwell. He won the 1991 NL Rookie of the Year award, then won the 1994 NL MVP and spent his entire Hall of Fame in an Astros uniform. Anderson left Boston as a free agent after that 1990 season.
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