There have been many MLB trade deadline deals that have setup franchises – or set them back. The following slideshow features the best and worst deadline deals from every team over the last 25 years. The trades all occurred in the month of July, prior to the July 31 deadline.
Arizona shipped a package of four players to Philadelphia for Schilling in 2000. While the package was productive for the Phils, including Omar Daal, Travis Lee and Vicente Padilla, Schilling joined Randy Johnson to win the World Series for the Diamondbacks in 2001. Over 2001 and 2002 in Arizona, Schilling would finish second in the NL Cy Young voting twice, averaging 258 innings and winning a total of 45 games.
Arizona sold low on Kennedy in 2013, trading him to San Diego for relievers Matt Stites and Joe Thatcher. Stites still hasn't panned out due to injuries, and Thatcher was a specialist over parts of two seasons in Arizona. Kennedy rebounded from his bad start in Arizona to post a 3.97 ERA in 73 starts over three seasons in San Diego.
San Diego traded McGriff to the Braves in 1993 for Vince Moore, Donnie Elliott and Melvin Nieves. The first baseman would play five seasons with the Braves, making three All-Star appearances. The only notable player the Braves traded was Nieves, who hit 20-plus home runs twice after going to Minnesota.
Teixeira was certainly a talented player, but the Braves overpaid to acquire him from Texas. The package included four major leaguers: Elvis Andrus, Neftali Feliz, Matt Harrison and Jarrod Saltalamacchia. While the Rangers never won a World Series with that group, they came awfully close in 2011. Teixeira was traded at the following trade deadline, as a pending free agent.
Uehara was a very good relief pitcher when the O's traded him in 2011, but he certainly wasn't worth Davis' eventual production. After showing inconsistency in three-plus seasons with Texas, Davis has averaged 37 home runs over his six full seasons in Baltimore. Hunter has also been a quality major league reliever.
Baltimore gave up on Arrieta at age 27, shipping him to the Cubs along with Strop for Feldman and Steve Clevenger. Arrieta won the NL Cy Young Award with Chicago in 2015 and was a key part of their 2016 World Series team, along with Strop. Feldman made only 15 starts for Baltimore before leaving in free agency.
If not the best, Theo Epstein's trade that sent franchise player Nomar Garciaparra packing for Cabrera and Mientkiewicz was certainly the gutsiest. The move vastly improved Boston's defense at shortstop and first base en route to breaking their World Series drought in 2004.
Boston trusted that they would be able to get the pre-2014 version of Craig when they acquired him and Kelly from the Cardinals for Lackey and a minor leaguer in a trade with St. Louis. Making it through only two years of a five-year, $30 million contract, Craig never found his way after the trade, while Lackey was highly productive for the Cardinals in 2014 and 2015 at minimal monetary cost. Kelly has eventually developed into a strong setup man.
One team's loss is another team's gain. The aforementioned worst trade for the Orioles helped the Cubs win the 2016 World Series, as Arrieta had 18 wins and a 3.10 ERA after winning the 2015 NL Cy Young. Strop has a 2.68 ERA in 339 appearances over his Cubs career.
Harden was an ace in Oakland when he was healthy, but those times were few and far between. The Cubs traded a package of youngsters that included Donaldson, Matt Murton, Sean Gallagher and Eric Patterson to Oakland in 2008 for Harden's services. Harden was great in 12 starts during 2008, with a 1.77 ERA, but struggled to stay healthy in his one full year in 2009, posting a 4.09 ERA in 26 starts. Donaldson eventually became a star third baseman with the A's.
The White Sox added Garland from their crosstown rivals for Karchern in 1998. The right-hander had a very productive career with the White Sox, posting a 4.41 ERA in eight seasons and making one All-Star appearance. Karchner made only 58 relief appearances over three seasons with the Cubs before his major league career ended.
The White Sox got 35 relief appearances out of Myers in 2012, trading a player to be named later to the Astros for his services. That PTBNL turned out to be Devenski, who has developed into one of the most dominant relievers in baseball.
Harang didn't look like much more than a fifth starter when the Reds acquired him, along with Jeff Bruksch and Joe Valentine, for Guillen. He turned out to be the team's ace for three years after being acquired in 2003. From 2005-07, Harang averaged 226 innings with a 3.77 ERA. Guillen was a rental for Oakland in 2003 and hit 19 or more home runs five more times in his career, but the Reds certainly got value.
Former Cardinals GM Walt Jocketty saw a golden opportunity to acquire his former third baseman, Rolen, from Toronto. He had to give up Encarnacion, Josh Roenicke and Zach Stewart to do so, unfortunately. Encarnacion became a star in Toronto, while Rolen had a very productive season with Cincy the following year in 2010 before faltering.
Cleveland found themselves in a three-way trade at the deadline in 2010, acquiring Kluber from San Diego for Westbrook. While Westbrook was a productive middle of the rotation starter, Kluber has developed into a Cy Young winner and surefire ace.
Cleveland needed help in their bullpen, acquiring Bob Wickman with Steve Woodard and Jason Bere thrown in from Milwaukee for Sexson, Kane Davis, Paul Ridgon and Marco Scutaro in 2000. Sexson averaged 40 home runs over the next three seasons and hit 306 home runs over 12 major league seasons. Scutaro would also eventually become a productive major league player.
Colorado made out like bandits during the 2000 trade deadline when they acquired Huskey and Walker. While Huskey wouldn't play another major league game after 2000, Walker hit .304-19-79 in 142 games over the next year for the Rockies. Sears would never pan out in the majors after going to Minnesota.
Colorado acquired Bruce Hurst and Greg Harris for a talented package of three players in 1993. Hurst started only three games for the Rockies, while Harris had an atrocious 6.60 ERA over two seasons. Hardly worth three eventually good major league players.
Fister was an underrated pitcher for the Tigers during his time with the team, posting a 3.29 ERA over parts of three seasons from 2011-13. The price for the Tigers was minimal, sending a group to Seattle that included Charlie Furbush, Casper Wells, Chance Ruffin and Francisco Martinez.
The players Detroit gave up for Washburn (Luke French and Mauricio Robles) were of little consequence, but the production the Tigers got out of Washburn couldn't have been much worse in 2009. He had a 7.33 ERA in eight starts, marking the end of his major league career.
Houston made a run in 1998, acquiring the Big Unit for two months. He went 10-1 with a 1.28 ERA over 11 starts, but Houston still fell in the playoffs. Seattle's return of Carlos Guillen, Freddy Garcia and John Halama hurt the Astros for years to come, but Johnson's incredible run can't be overlooked.
Houston's trade of Zobrist in 2006 eventually cost them dearly, moving the middling prospect and Mitch Talbot for Aubrey Huff. Huff hit .250-13-38 in 68 games as a rental, while Zobrist became an All-Star in Tampa Bay.
If not the best trade the Royals have made in the last 25 years, KC's acquisition of Cueto from Cincinnati in 2015 was certainly the most important. The jury is still out on the package of three pitchers the Royals sent to the Reds, including Brandon Finnegan and Cody Reed, but Cueto went 2-1 in four playoff starts, including a complete game in the World Series.
The Royals traded a young third baseman to the Mets for Huber in a prospect swap. Huber had 175 career plate appearances, while Bautista went on to become a six-time All-Star following the 2004 trade.
The Angels tried to make a playoff run in 2008, acquiring Teixeira from the Braves for pennies on the dollar. They moved Casey Kotchman and Stephen Marek to acquire him. Once an elite prospect, Kotchman continued to disappoint in Atlanta, posting a .724 OPS over two seasons.
The Angels paid dearly for two months of Greinke in 2012, moving a future franchise shortstop in Segura to Milwaukee. Greinke had a 3.53 ERA in 13 starts, as the Angels failed to make the playoffs.
The Dodgers pulled off an unbelievable heist in 2015, in a trade that also involved Atlanta and Miami. Going to LA were Alex Wood, Jose Peraza, Jim Johnson, Luis Avilan, Bronson Arroyo, Mat Latos and Mike Morse. None of the prospects the Dodgers traded have panned out, and Olivera's MLB career effectively ended after he got into trouble off the field. Wood pitched like an ace for LA and was an All-Star in 2017, while Avilan was a key part of the bullpen.
The Dodgers paid up to acquire a closer in 1998, sending a top first base prospect to the White Sox for Shaw. Shaw recorded 129 saves over four seasons in LA, but Konerko became one of the greatest and most beloved White Sox players ever. He hit 432 home runs over 16 seasons on the South Side.
Miami got a huge return for Mantei from Arizona in 1999, acquiring Penny, Vladimir Nunez and Abraham Nunez. Vladimir Nunez had a short run as a reliever for the Marlins, and Penny was a quality starter over six seasons before getting traded to the Dodgers in 2004. Mantei was inconsistent over six seasons in Arizona, though he did convert 74 saves.
Gonzalez was a former No. 1 overall pick by the Marlins, but his slow development spurred the Marlins to trade him for a closer in 2003. Gonzalez didn't breakout in the majors until 2006, but he's been a five-time All-Star. Urbina posted a 1.41 ERA down the stretch for the Marlins and helped them win a World Series, but the long-term impact was certainly felt by the organization.
The aforementioned worst trade for Cleveland setup Milwaukee long-term at first base with Sexson, with the only major price being Bob Wickman. Not only did Milwaukee get a top power-hitting first baseman in 2000, but they also received Kane Davis, Paul Rigdon and soon-to-be-known farmhand Marco Scutaro.
Milwaukee acquired Francisco Cordero, Kevin Mench, Laynce Nix and minor leaguer Julian Cordero for Cruz and Lee in 2006. Among the group, only Cordero helped the Brewers, while Lee continued to produce like an All-Star down the stretch and Cruz eventually emerged as an elite power hitter for Texas.
While Bartlett didn't do much for the Twins organization, he was a steal for a backup outfielder like Buchanan in 2002. After leaving the Twins, Buchanan played only two more major league seasons. Bartlett started for the Twins in 2007 at shortstop and eventually became an All-Star in Tampa Bay.
A couple of poor seasons spurred the Twins to trade Erickson to Baltimore in 1995 for Bartee. Erickson was able to find himself with the Orioles, posting a 3.89 ERA the rest of the season and averaged 231 innings with a 4.38 ERA over the following four years. Bartee had a very brief major league career.
In a deal that worked out extremely well for both sides, the Mets traded two strong pitching prospects for Cespedes from the Tigers in 2015. Cespedes played like an MVP down the stretch, and nearly won the Mets a World Series. Fulmer has emerged as an ace in Detroit, and Cessa has shown flashes with the Yankees.
Mets fans can still be heard cursing about this 2004 trade. New York sent their best pitching prospect to Tampa Bay for Zambrano, a hard-throwing starter who never established his control. Kazmir went on to make two All-Star appearances in Tampa Bay, though he wasn't quite as good as expected due to injuries. On the other hand, Zambrano had a 4.42 ERA and threw 201.2 innings over three seasons in New York. Of course, the Mets have plenty more awful trades from the last 25 years that can be mentioned here.
The jury is still out on the total impact of 2016's Miller to Cleveland package, but it's already helping the Yankees. They were able to acquire Clint Frazier and Ben Heller, two major leaguers already, while Justus Sheffield is one of the organization's top pitching prospects. Frazier and Sheffield have the makings of a great long-term combination. While Miller helped the Indians to the AL pennant, the price was well worth it for the Bronx Bombers.
New York figured they were upgrading at third base when they acquired Headley from the Padres for Solarte and De Paula in 2014. As it turns out, Solarte has been the better and much cheaper player since the deal, with a .750 OPS, while Headley had just a .727 OPS in New York and is now back in San Diego. De Paula is also a possible major league player as a reliever.
Donaldson wasn't the featured part of a four-player prospect package the A's received from the Cubs for Rich Harden and Chad Gaudin in 2008, but he turned out to be the best part. He became a star in Oakland before getting traded to Toronto in 2015.
The price of prospects Brett Wallace, Clayton Mortensen and Shane Peterson was considered steep in 2009, but as it turns out, the A's got almost nothing for Holliday when they shipped him to St. Louis. After trading Carlos Gonzalez, Huston Street and Greg Smith to the Rockies to acquire Holliday in the previous offseason, Oakland certainly took a major long-term hit.
What's a playoff ace worth? For the Phillies, it was a package of four young players: Jason Knapp, Carlos Carrasco, Jason Donald and Lou Marson in 2009. While Carrasco has emerged as a very good starter for the Indians, the deal was well worth it for Philly after Lee allowed only seven earned runs in 40.1 incredible playoff innings.
Philadelphia moved Schilling in 2000 for Omar Daal, Nelson Figueroa, Travis Lee and Vicente Padilla. Schilling went on to win a World Series the following year with Arizona alongside Randy Johnson as one of the elite pitchers in baseball. While all four players were useful for Philadelphia, only Padilla had what could be considered a very good career with the team.
While it's still very early, GM Neal Huntington's gutsy trade of Melancon last year is looking like a coup for Pittsburgh. Still in contention, the Pirates moved their pending free agent closer for Rivero and Hearn. Rivero has emerged as an elite reliever, with a 2.38 ERA and 44 saves. Hearn has also shown himself to be a viable pitching prospect rising the ranks of the farm system.
In a move that also drew scorn at the time, Pittsburgh traded Ramirez and Lofton to the Cubs for Jose Hernandez, Bobby Hill and Matt Bruback in 2003. Ramirez was only 25 and formerly hit 34 home runs. He went on to average .297-28-96 over eight seasons in Chicago. Pittsburgh's return netted a .608 OPS the rest of the year from Hernandez, along with two failed prospects.
Ashby and Ausmus were excellent players for San Diego, and the cost at the 1993 deadline of Greg Harris and Bruce Hurst was minimal. Ashby had a 3.59 ERA over eight seasons for the Padres, while Ausmus started at catcher in San Diego for nearly three years before going to Detroit.
The Padres acquired Ludwick from the Cardinals in a three-way trade for Kluber, a low minors pitching prospect. Ludwick posted a .659 OPS for the Padres over parts of two seasons, while Kluber became a Cy Young winner in Cleveland.
Pittsburgh gave up on Schmidt a bit too early. After he was traded to San Francisco in 2001, Schmidt emerged as an ace, posting a 3.36 ERA in 162 starts over six seasons. Neither Rios nor Vogelsong did much for Pittsburgh during their post-trade stints.
The Giants sent a prospect package to the White Sox for pitchers Wilson Alvarez, Danny Darwin and Roberto Hernandez in 1997. That package included eventual closers Foulke and Howry, while the package that the Giants received made very limited contributions.
Seattle acquired an emerging 33-year-old lefty from Boston in 1996. A late bloomer, Moyer went on to pitch 11 seasons for Seattle, winning 145 games with a 3.97 ERA. Bragg had an 11-year career, mostly as a bench player.
Seattle's 1997 acquisition of Slocumb didn't turn out well, to say the least. Slocumb was struggling during that season and posted a 5.32 ERA the following year in Seattle. Lowe and Varitek turned out to be key pieces of Boston's 2004 World Series team, with Varitek becoming the team captain.
The Cardinals have made plenty of great deadline deals over the last 25 years, but it's difficult to top the deal they made to acquire McGwire in 1997. The team moved Eric Ludwick, T.J. Mathews and Blake Stein for McGwire. Big Mac went on to break MLB's single-season home run record in 1998 with 70 home runs and hit 65 home runs the following year. Over four seasons in St. Louis, McGwire had a staggering 1.111 OPS.
The Cardinals haven't made many deadline deals that have gone wrong, but they probably regretted overpaying for Christiansen from Pittsburgh in 2000. Wilson had a solid career as a starting shortstop, while Christiansen had a 4.91 ERA over two seasons as a specialist in St. Louis.
The worst trade for Houston worked out quite well for Tampa Bay. Zobrist turned into an All-Star, as a versatile power hitter for Joe Maddon. Huff was just a rental for Houston before a few more productive seasons.
A very bad Devil Rays team got younger with Abernathy, but they certainly didn't get better after this trade with the Jays in 2000. Trachsel was solid over six seasons in New York, posting a 4.09 ERA over 160 starts, and Guthrie had a couple more strong seasons in relief. Abernathy was a bust, starting at second base for parts of two seasons and finishing his career with a .622 OPS.
Mark Teixeira was a franchise player for the Rangers, but the team got a franchise-altering return from the Braves in 2007. The return included a star shortstop (Elvis Andrus), closer (Neftali Feliz), middle of the rotation starter (Matt Harrison) and power-hitting catcher (Jarrod Saltalamacchia) that set the table for playoff runs over the next several seasons.
Texas sent two minor leaguers, Hendricks and Christian Villanueva, to the Cubs for Dempster in 2012. Villanueva was the more highly regarded prospect at the time, but Hendricks pitched like an ace during Chicago's 2016 World Series season. Dempster posted an ERA above 5.00 in 12 starts for Texas and retired following the next year.
With Rolen approaching the end of his career, the Blue Jays traded the third baseman to Cincinnati for Encarnacion, Josh Roenicke and Zach Stewart in 2009. Encarnacion eventually became the team's cleanup hitter, hitting 239 home runs with an .878 OPS over eight seasons.
Loaiza never panned out after the Jays acquired him from Texas in 2000, posting a 4.96 ERA in three seasons. Young went on to have a great career in Texas, with seven All-Star appearances.
Sometimes the best trades can look the most meaningless at the time. Washington cashed in on Guzman in 2010, trading him to Texas for Ryan Tatusko and Roark. Roark has been a solid middle of the rotation start for the Nats over the last few seasons (3.60 ERA) before having a tough current stretch, while Guzman saw 50 plate appearances for the Rangers before we stopped hearing about him.
Less than three weeks after acquiring Floyd from the Marlins in 2002, Montreal turned around and sent him to Boston for Seung Song and Sun-Woo Kim. Neither pitcher panned out, while Floyd had a .935 OPS for Boston down the stretch before going to the Mets.
Seth Trachtman is a sportswriter, digital marketer, and fantasy sports expert based in St. Louis, Missouri. He’s a two-time winner of the Tout Wars Fantasy Baseball Expert’s League, and his work has appeared in hundreds of fantasy baseball and fantasy football newsstand and online publications
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