Arizona – Atlanta – Baltimore – Boston – Chicago Cubs
Chicago White Sox – Cincinnati – Cleveland – Colorado – Detroit
Houston – Kansas City – LA Angels – LA Dodgers – Miami
Milwaukee – Minnesota – New York Mets – New York Yankees – Oakland
Philadelphia – Pittsburgh – St. Louis – San Diego – San Francisco
Seattle – Tampa Bay – Texas – Toronto – Washington
Chicago White Sox
Best trade: Acquired Jose Contreras from Yankees for Esteban Loaiza (July 31, 2004)
This was one of Kenny Williams’s best move in charge of the White Sox. Esteban Loaiza was coming off a 2003 season when he was the runner-up for the AL Cy Young award. 2004 was his second straight All-Star season, but his ERA was approaching 5.00 at the trade deadline. So Williams shipped him off to the Bronx for Jose Contreras, the Cuban that had earned a ridiculous contract from the Yankees just a year and a half earlier, but had disappointed in 36 games with the club. With the Sox, Contreras struggled over the rest of 2004, but had the best year of his career in 2005, making 32 starting and itching to a 3.61 ERA while helping the team win the World Series. He’d go on to stay with the White Sox until 2009, when he was dealt to the Rockies. As for Loaiza, he had an 8.50 ERA in ten appearances with the Yankees, left town as a free agent that winter, and kicked around with various teams over the final four seasons of his career, closing things out with the White Sox in 2008.
Worst trade: Acquired Jon Adkins from Athletics for Ray Durham (July 25, 2002)
Durham was a speedy second baseman with some pop that was on the wrong age of 30 and about to hit free agency. Needless to say, the White Sox had to trade him, and that they did. Durham played well with the A’s, then signed with the Giants that winter and played another six seasons in the majors at an above average level (aside from his lost 2007). Adkins did nothing in Chicago, pitching to a 5.08 ERA in 79 2/3 innings over three seasons before leaving town. So what makes this deal so bad?
After Durham was dealt, the White Sox spiraled into an endless spell of mediocrity at second base. In the second half of 2002, the position was manned by journeymen Willie Harris, Tony Graffanino, and D’Angelo Jimenez. Jimenez took over the position for the first half of 2003 before being dealt, leading to the aging Roberto Alomar being acquired for the stretch run. Alomar bombed in his half season, and the bulk of the playing time in 2004 went to Harris and Juan Uribe, who was good in 2004, but awful during the rest of his career on the south side. Japanese import Tadahito Iguchi took over in 2005, and he only lasted until the middle of 2007, when he was moved and replaced by Danny Richar. The position was finally solidified in 2008 by Uribe and Cuban signee Alexei Ramirez, who then ceded the position to Chris Getz and eventually, Gordon Beckham. After all that…gee, they should have just re-signed Durham.
Best trade: Acquired Brandon Phillips from Indians for Jeff Stevens (April 7, 2006)
Just days after the 2006 season began, the Indians dumped off Brandon Phillips on their in-state rivals. Phillips had struggled both on and off the field with Cleveland, and they simply wanted to get a warm body for him, which is a perfect description of Stevens. who never pitched in the majors for the Indians. He was later part of another lopsided trade, getting dealt to the Cubs along with Chris Archer in exchange for half a season of Mark DeRosa. I don’t think I need to elaborate how good Phillips has been as a Red – he’s won four Gold Gloves and made three All-Star teams with Cincinnati.
Worst trade: Acquired Juan Guzman from Orioles for B.J. Ryan and Jacobo Sequea (July 31, 1999)
This one is really splitting hairs, but whatever. Juan Guzman was actually pretty good for the Reds, pitching to a 3.03 ERA in 12 starts. He signed as a free agent with the Devil Rays that winter, and made just one more start before his career was over. Meanwhile, the Reds lost in the Wild Card tiebreaker to the Mets, and B.J. Ryan, who had just been drafted by the Reds the summer before he was traded, spent seven years in the Orioles’ bullpen, pitching to a 3.54 ERA in 379 1/3 innings and earning the team a couple of draft picks when he signed an absurd free agent contract with the Blue Jays a few seasons later.
Best trade: Acquired Cliff Lee, Brandon Phillips, Grady Sizemore, and Lee Stevens from Expos for Bartolo Colon and Tim Drew (June 27, 2002)
Man, where do we even begin with this one? Colon has having a fine year in 2002, but was just a year and a half away from free agency when the Expos came calling. Seven months later, Colon would be traded to the White Sox for a pupu platter worth of talent, though he did pitch to a 3.31 ERA and 10-4 record in 17 starts with Montreal. Drew spent two years with the Expos, and was out of the majors for good after the 2004 season.
Then, there’s the return for Colon. We already went over Phillips’ disastrous tenure in Cleveland. But Cliff Lee had a 4.01 ERA in 1,117 innings as an Indian, and won the 2008 AL Cy Young award before being dealt to the Indians. Before injuries killed his career, Sizemore was continually one of the best players in the American League, stealing 134 bases and homering 139 times in 892 games with the Indians while making three All-Star Games, receiving MVP votes in four years, winning two Gold Gloves, and winning a Silver Slugger. Lee Stevens’ major league career ended after his brief stint with the Tribe. But nevertheless, getting a return that includes multiple All-Star appearances and a Cy Young award for a guy who was a year and a half from free agency is a boon for any team looking to deal at the deadline.
There are plenty of other honorable mentions here – the Indians know what they’re doing at the deadline. They acquired Justin Masterson for Victor Martinez, Carlos Santana for Casey Blake, Zach McAllister for Austin Kearns, and Corey Kluber for Jake Westbrook in the last few seasons. In earlier years, Michael Brantley was part of the C.C. Sabathia return, Shin-Soo Choo was acquired for Ben Broussard, and Coco Crisp came over for Chuck Finley.
Worst trade: Acquired Carlos Carrasco, Jason Donald, Jason Knapp, and Lou Marson from Phillies for Cliff Lee and Ben Francisco (July 29, 2009)
For as great as Cleveland has been when it comes to working the trade deadline, this was a rare miss from them. The 2008 Cy Young winner Lee was traded to the Phillies for a four-player package that ended up as a disappointment. But then again, every team that trades Lee ends up worse off than if they would have just kept him in the first place. Carrasco is the lone member of the trade still contributing for the Indians, working mostly as a reliever this season. In his major league career, he has a 4.98 ERA in 294 2/3 innings. After the trade, Knapp threw just 40 innings with the Indians organization due to a number of shoulder problems. Donald hit .257/.309/.362 in three years with the Indians as a utility player, and hasn’t been in the majors since 2012. He’s currently in the minors with the Rangers. And then there’s Marson, who hit .217/.308/.295 in parts of five seasons as the Indians’ backup catcher, and is now in the minors with the Reds.
Best trade: Acquired Todd Walker and Butch Huskey from Twins for Todd Sears (July 15, 2000)
Sears got a total of 94 plate appearances in the majors. Huskey’s career was over after the 2000 season, but hit .348/.432/.565 in 45 games for the Rockies. Walker was the real prize, spending just over a year with the team and hitting .304/.363/.514 with 19 homers. Of course, Colorado traded Walker to the Reds a year later for Alex Ochoa, whose major league career was over after the 2002 season.
Man, the Rockies don’t really make a lot of trades in the middle of the season.
Worst trade: Acquired Joe Gardner, Matt McBride, Drew Pomeranz, and Alex White from Indians for Ubaldo Jimenez (July 30, 2011)
Jimenez was always a pitcher that seemed like his bubble was about to burst, so I can’t fault the Rockies for selling high on him. The only issue with this deal is well…it didn’t help them too much at all. White made 30 appearances for Colorado and had a 6.30 ERA before being dealt to the Astros as part of the Wilton Lopez trade. Pomeranz has a 5.20 ERA in 51 games as a Rockie before being sent to the A’s for Brett Anderson. Gardner never made the majors and is now in the Cubs organization. McBride has just 81 major league plate appearances, and is currently a 29-year old in AAA. Jimenez had an often frustrating run with the Indians, pitching to a 4.45 ERA in 74 starts, but helped the team make the playoffs in 2013 and earned them a draft pick when he signed with the Orioles this past winter.
Best trade: Acquired Doug Fister and David Pauley from Mariners for Francisco Martinez, Charlie Furbush, Casper Wells, and Chance Ruffin (July 30, 2011)
This ended very well for the Tigers. Fister had a 3.21 ERA in 70 appearances for the Tigers, and was a key part of their playoff teams in 2011, 2012, and 2013. Detroit dealt him to the Nationals this winter in a controversial and, quite frankly, bizarre deal. Pauley had a 5.95 ERA with the Tigers and was released. The Mariners got next to nothing in return, as Martinez has found his way back to the Tigers, Wells has been passed around like a hot potato since the trade, and Ruffin had a 5.70 ERA with Seattle before retiring. The only real loss was Furbush, who has a 4.30 ERA with the Mariners and has blossomed into a solid reliever since being shifted to the bullpen. I think the Tigers wouldn’t mind doing this trade again.
Worst trade: Acquired Jarrod Washburn from the Mariners for Luke French and Mauricio Robles (July 31, 2009)
Neither French nor Robles did much of anything in the majors. But this isn’t about them – it’s about Washburn. After posting a 2.64 ERA in the first half with Seattle, he was supposed to shore up the Tigers rotation as they attempted to march to the division title. Instead, Washburn had a 7.33 ERA in eight starts and started only two games in September. Detroit lost a tiebreaker game to the Twins for the AL Central title, and Washburn never pitched in the majors again. That ended well.