Best and worst in-season trades for each franchise over the last 20 years

The big midseason trade can have a vast array of effects on a team, but there are obviously two extreme scenarios – a World Championship on one hand, and a complete disaster on the other. But really, most trades fall somewhere in the middle. We decided it would be a good idea, just a week and a half before the deadline, to revisit each team’s biggest triumph and biggest misstep of the last 20 years, dating all the way back to the 1994 season and the birth of the Wild Card (that we didn’t get to see implemented until 1995).

The trades will be focusing on here had to have taken place between April and September. Context is also important – if a team trades a star for prospects that don’t pan out, that’s not nearly as bad as them trading a young player that becomes a star for a veteran that flops.

And hey, because this article is massive, here are quick links for all 30 teams in case you want to duck out early.
ArizonaAtlantaBaltimoreBostonChicago Cubs
Chicago White Sox – CincinnatiClevelandColoradoDetroit
HoustonKansas City – LA AngelsLA DodgersMiami
MilwaukeeMinnesotaNew York Mets – New York YankeesOakland
PhiladelphiaPittsburghSt. LouisSan Diego – San Francisco
SeattleTampa BayTexasTorontoWashington

Arizona Diamondbacks
Best trade: Acquired Curt Schilling from Phillies for Omar Daal, Nelson Figueroa, Travis Lee, and Vicente Padilla (July 26, 2000)
Schilling was already 33 when the Diamondbacks picked him up from the Phillies. He didn’t help them much in 2000, when the team won 85 games and finished nine games out of a playoff spot. But in 2001, Schilling partnered with Randy Johnson to lead Arizona to their first (and only) World Championship. He was the an All-Star and the Cy Young runner-up in both 2001 and 2002, and had a 3.14 ERA in his three and a half seasons in the desert. Of the four players traded to Philadelphia, Padilla was the only one that stuck around past the 2002 season.

Worst trade: Traded Ian Kennedy to Padres for Matt Stites and Joe Thatcher (July 31, 2013)
I’m grasping at straws a bit here, because in all honesty, the Diamondbacks haven’t made many blatantly terrible trades in the middle of the season since their inception. But they traded Kennedy, who was 28 at the time, still had two seasons of control, and was fourth in the NL Cy Young voting in 2011, for a pair of relievers. A year later, Thatcher has already been dealt to Angels and Stites had a 5.06 ERA in 10 2/3 major league innings for Arizona. Meanwhile, Kennedy has flourished in San Diego, and is one of this summer’s hottest trade targets. If the Padres deal him, they’ll really have just dealt a pair of relievers for their entire return for Kennedy, along with a full season of above average performance.

Daniel Shirey-USA TODAY Sports

Atlanta Braves
Best trade: Acquired Michael Bourn from Astros for Juan Abreu, Paul Clemens, Brett Oberholtzer, and Jordan Schafer (July 31, 2011)
Let’s start with the return first. Abreu was a depth reliever who pitched 6 2/3 innings for the Astros before being lost on waivers to the Blue Jays. Schafer was a fifth outfielder who had a .220/.301/.298 line in Houston before being lost on waivers…to the Braves. Clemens has a 5.57 ERA in 97 innings with the Astros. Oberholtzer was the only real loss, thanks to his 3.62 ERA in 141 2/3 major league innings. But Bourn provided more than enough value for Atlanta, hitting .275./341/.381 with the Braves while stealing 64 bases and making the 2012 NL All-Star team. Atlanta let him walk after the 2012 season, and received a sandwich pick at the end of the first round as compensation. Hey, not bad.

Worst trade: Acquired Nate McLouth from Pirates for Gorkys Hernandez, Jeff Locke, and Charlie Morton (June 3, 2009)
McLouth was half a season into what looked like a team-friendly three-year contract, and was coming off an All-Star season in 2008. In his two and a half years with the Braves, McLouth hit .229/.335/.364, and he was reduced to a bench role in 2010. As for the three players traded for him, Hernandez didn’t make much of an impact anywhere, but was traded by the Pirates to the Marlins in the Gaby Sanchez trade. Locke has a 3.82 ERA in 50 major league games for Pittsburgh, and was an All-Star in 2013. And then there’s Morton, who has made 112 starts over six seasons with the Pirates and has come into his own over the last four years, pitching to a 3.64 ERA while also missing the bulk of a season thanks to Tommy John surgery.

*NOTE*: I’m avoiding the Mark Teixeira trade because was awesome in his two half seasons as a Brave, and Atlanta had depth at all of the positions they traded from to acquire him.

Toronto Blue Jays v Baltimore Orioles

Baltimore Orioles
Best trade: Acquired Melvin Mora, Mike Kinkade, Leslie Brea, and Pat Gorman from Orioles for Mike Bordick (July 28, 2000)
The Orioles have done most of their fleecing (notably, the Miguel Tejada and Erik Bedard blockbusters) in the offseason, but this trade that they pulled off in the summer of 2000 was a heist. All Baltimore had to give up for these four players was Mike Bordick, an all-glove shortstop that made the 2000 All-Star Team and hit .260/.321/.365 in 56 games with New York after the deal, going without an extra base hit in the entire 2000 playoffs. And while three of the four players that Baltimore received in the deal didn’t accomplish much of anything in the majors, Mora spent ten seasons as an Oriole, hitting .280/.355/.438, making a pair of All-Star teams, winning a Silver Slugger in 2004, and playing every position on the diamond except pitcher and catcher. To add insult to injury, Bordick didn’t even re-sign with the Mets after the 2000 season – he went back to Baltimore.

Worst trade: Acquired Scott Feldman and Steve Clevenger from Cubs for Jake Arrieta, Pedro Strop, and cash (July 2, 2013)
A trade that took place a year ago is the worst one the Orioles have made in the last 20 years, and I think that speaks well about what they’ve done during the season over that time period. The club acquired Feldman and Bud Norris to shore up their rotation for a potential playoff push last year, and that push fell flat, as the team ended up winning 85 games and finishing third in the AL East. Feldman pitched reasonably well in his 15 starts as an Oriole, notching a 4.27 ERA in 90 2/3 innings. This past offseason, he signed as a free agent with the Astros. The 28-year old Clevenger is simply catching depth for the club. As for what they traded for Feldman, Strop has blossomed into a solid reliever with the Cubs, pitching to a 2.97 ERA in 66 2/3 innings with his new team. The real prize, however, was Arrieta, who has finally tapped into his massive potential as a Cub. In 22 starts dating back to 2013, Arrieta has a 2.63 ERA with Chicago, striking out 122 and walking 46 in 130 innings. The move had to be made, as Arrieta was never able to thrive in the majors with Baltimore, but the Orioles might end up regretting this one for years to come.

Greg M. Cooper-USA TODAY Sports

Boston Red Sox
Best trade: Acquired Derek Lowe and Jason Varitek from Mariners for Heathcliff Slocumb (July 31, 1997)
Talk about the four-team trade in the middle of the 2004 season all you want. This trade is the one that really began the march to Boston’s 2004 World Championship. The Red Sox traded Slocumb, a journeyman reliever who had a 5.79 ERA in 49 games in 1997, for a pair of players that would become franchise cornerstones. Slocumb didn’t even contribute much positive value for Seattle in his year and a half in the Pacific Northwest, pitching to a 4.97 ERA in 96 innings. Lowe would pitch 1,037 innings over his career with Boston, winning 70 games, saving 85, and notching a 3.72 ERA. Varitek spent his entire career with the Red Sox, making three All-Star teams and winning a pair of World Championships as Boston’s primary catcher. Hey, not bad.

Worst trade: Acquired Eric Gagne from Rangers for Engel Beltre, Kason Gabbard, and David Murphy (July 31, 2007)
The Red Sox won the 2007 World Series in spite of trading for Gagne, not because of trading for him. The former Cy Young winner stunk with Boston, pitching to a 6.75 ERA in 18 2/3 innings and really doing nothing to ease the pressure on the Red Sox bullpen. Of the five games he pitched in the 2007 playoffs, only one wasn’t mop-up duty – and that was an 11 inning game that the Red Sox lost 13.6. His career would be over after 2008. Murphy became a solid corner outfielder for the Rangers that earned a multi-year contract from the Indians this past winter while Beltre is still only 24, but has been hampered by injuries. Gabbard flamed out pretty quickly, but the nearly 3,000 plate appearances Murphy gave the Rangers in exchange for that performance by Gagne was more than enough to tilt this deal in favor of Texas.


Chicago Cubs
Best trade: Acquired Aramis Ramirez, Kenny Lofton, and cash from Pirates for Matt Bruback, Jose Hernandez, and Bobby Hill (July 23, 2003)
Ramirez was only 25 when the Cubs acquired him, and while he had shown flashes of brilliance in Pittsburgh, he still didn’t have that breakout season. He was also starting to get expensive in his arbitration years. As a Cub, Ramirez hit .294/.356/.531 and became one of the best third basemen in the National League, making two All-Star Games and receiving MVP votes in four seasons as a Cub. Lofton also played well in his one season on the north side, hitting .327/.381/.471 and stealing 12 bases in 56 games. The pair nearly helped the Cubs to the World Series, if only that Bartman character wasn’t involved. All they gave up for the pair was a player who never made the majors (Bruback), an infielder who never played in the majors after 2005 (Hill), and a journeyman utility player that the Pirates released after the 2003 season (Hernandez). Talk about a slam dunk.

Worst trade: Acquired Rick Aguilera and Scott Downs from Twins for Kyle Lohse and Jason Ryan (May 21, 1999)
This trade actually starts with a trade completed the prior November, in which the Cubs traded Downs to the Twins as the player to be named later in exchange for Mike Morgan, who made five starts of 7.15 ERA baseball for the Cubs that summer. So anyway, the Cubs then re-acquired Downs, along with veteran closer Rick Aguilera, in exchange for a pair of minor league pitchers, Kyle Lohse and Jason Ryan. Aguilera spent a year and a half in Chicago to end his career, pitching to a 4.31 ERA in 94 innings and saving 37 games. He retired after the 2000 season. Downs lasted a full year with the Cubs on this go-around, but was traded to the Expos after 18 starts in 2000 in exchange for Rondell White.

White played very well off the bench for the Cubs until signing with the Yankees after the 2001 season. Ryan was done after 24 games in the majors, but Lohse threw 908 1/3 innings with the Twins and another 1390 1/3 innings with other National League teams, making appearances in six different postseasons for three different teams. Downs has also stuck around in the majors, and has thrived since becoming a full-time reliever in 2007 with the Blue Jays. And the Cubs gave those two players away for a season and a half each of Rick Aguilera and Rondell White, and five starts from Mike Morgan. None of these three trades were franchise crippling moves, but the Cubs sure would have been in a better place today if they just ignored the Twins’ phone calls.


About Joe Lucia

I'm the managing editor of Awful Announcing and the news editor of The Comeback. I also made The Outside Corner a thing for six seasons.