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 Paul Konerko from Reds for Mike Cameron (November 11, 1998)
Cameron had a decent one year with Cincinnati – he hit .256/.357/.469 with 21 homers before getting traded to Seattle in the Ken Griffey Jr. trade, where he starred for four years before turning into, essentially, a journeyman.
At the time of the trade, Paul Konerko was still just a 22-year old, moving on to his third organization. I don’t think anyone could have expected what he’d do on the South Side of Chicago. Konerko played 16 years with the Pale Hose, launching 432 homers and hitting .281/.356/.491. He was a six-time All-Star and received MVP votes in five seasons, two of which saw him finish in the top ten of the AL voting. Before he began to break down in 2013, Konerko was also the model of consistency with the White Sox – he played in at least 140 games and posted an OPS+ of at least 100 in all but one season from 1999-2012. And hey, Konerko was also a key contributor for Chicago’s 2005 World Championship team – flags fly forever.
Worst trade: Acquired Travis Hinton, Scott Podsednik, and Luis Vizcaino from Brewers for Carlos Lee (December 13, 2004)
This is a strange one, but I went with this trade because the White Sox could have done *a lot* better in trading Lee. He was a productive player in his season and a half with Milwaukee, making a pair of NL All-Star Teams and hitting .273/.333/.511 with 60 homers. The Brewers traded him to the Rangers at the 2006 trade deadline (with Nelson Cruz!) for a package of four plaeyrs highlighted by future closer Francisco Cordero.
The package that the White Sox received was thoroughly underwhelming. Hinton was a player to be named later in the deal, and played just one season following the trade (at high-A, mind you) before leaving baseball. Vizcaino had a 3.73 ERA in 70 innings with the White Sox in 2005, and was traded to Arizona following the season as part of the Javier Vazquez trade. Podsednik was the “win” of the return, but even then, his only value was on the basepaths, and even that was minimal. In four seasons with the White Sox, he hit .280/.339/.371 and stole 141 bases, albeit at a 70.1% clip (which isn’t great). He was also an AL All-Star in 2005, a year that saw him also finish 12th in AL MVP voting. Given what was going on in the baseball world at the time, getting a light-hitting fourth outfielder (who wasn’t used as a fourth outfielder) and a replaceable bullpen piece wasn’t a good return for a fantastic power hitter with two years of control left.
Cincinnati Reds
Best trade: Acquired Sean Casey from Indians for Dave Burba (March 30, 1998)
Cleveland punted on a 22-year old Casey after just 12 plate appearances, but given the presence of Jim Thome at first base, it was at least understandable. Their loss was Cincinnati’s gain, because Casey enjoyed a fine eight years with the Reds. He made three All-Star teams and hit .305/.371/.463 with 118 homers over those eight years, but he struggled once the Reds traded him to the Pirates following the 2005 season, leading to his retirement after 69 games with Boston in 2008.
As for Burba, he still pitched seven seasons after the trade, spending time with four different clubs. In 1,031 1/3 innings, he pitched to a 4.65 ERA (which actually led to a 102 ERA+ during the height of the steroid era), and had the same ERA in four seasons with Cleveland immediately following the Casey trade. Those Indians teams of the mid to late ’90s were awesome, completely loaded with young talent, and sometimes, they had to sell low on that young talent to fill a hole or two. But if you thought the Casey trade was bad, you haven’t seen anything yet…give me a minute, here.
Worst trade: Acquired Danny Herrera and Edinson Volquez from Rangers for Josh Hamilton (December 21, 2007)
I can’t really fault the Reds all that much for the logic behind this trade, as Hamilton was a 26-year old coming off a 90 game rookie year in 2007…but they got robbed here. Herrera pitched in parts of three seasons with Cincinnati, and pitched to a 3.62 ERA in 92 innings before being claimed on waivers by the Brewers. Volquez made the 2008 All-Star team with Cincinnati and finished fourth in the NL Rookie of the Year voting (DESPITE NOT BEING A ROOKIE!), but that was the high water mark during his tenure with the Reds – he’d throw just 221 innings of 5.01 ERA baseball from 2009-11 before he was dumped on the Padres as part of the Mat Latos trade.
Hamilton obviously thrived in Texas before falling off a cliff once the Angels gave him a ridiculous $125 million contract. In his five years with the Rangers, Hamilton was a five-time All-Star, received MVP votes in four years, and won three Silver Slugger awards. In 2010, he won the AL batting title and coasted his way to the AL MVP award. Injuries did play a part in his tenure with the Rangers – Hamilton played in just 647 of a total 810 games. His Postseason performance with the Rangers was also erratic – he won the 2010 ALCS MVP award, but hit .100/.143/.250 in the subsequent World Series. He was essentially a non-factor in the Rangers’ 2011 Postseason run, homering just once in 17 games. But let’s be honest with ourselves here – Texas traded an organizational reliever and a shaky starting pitcher for a player who’d end up hitting .305/.363/.549 with 142 homers in five seasons with the team. You do that every day of the week.
Cleveland Indians
Best trade: Acquired Travis Hafner and Aaron Myette from Rangers for Einar Diaz and Ryan Drese (December 6, 2002)
When I was a teenager 12 years ago and saw this trade run across the ESPN crawl, I was baffled even then. Hafner was a crusher! Diaz was a catcher! Drese had the ceiling of a back-end starter! What the hell? My teenage intuition ended up being spot on. Diaz spent just one year with Texas, and hit .257/.294/.341 in 101 games. Inexplicably, the Rangers managed to trade him for Chris Young, The Pitcher, who they’d later spin off in an even worse trade than the Hafner one. Drese had a 5.07 ERA in 323 1/3 innings with the Rangers, and was out of the majors in 2006 at the age of 30.
Myette wasn’t much of anything – he’d spent the rest of his major league career in Ohio, allowing 11 runs in seven innings with the Indians and Reds. But Hafner would be an excellent, although injury-prone, contributor for the Tribe for the next decade. Sure, he only played in 1,078 games over those ten years, but he hit .278/.382/.509 while serving as Cleveland’s primary DH. He received MVP votes in each year from 2004-2006, finishing in the top ten in 2005 and 2006. He led the AL in OPS in 2006 after an absurd 42 homer, .308/.439/.659 season. The Indians ended up taking it too far however, and paid Hafner $49 million from 2009-2012. He played in 372 games over those four seasons, and hit just 54 homers with a .268/.361/.453 line. Still productive, but not healthy enough to warrant that salary. Nevertheless, Cleveland traded two marginal players for a guy who would be a key part of their lineup in the post-Thome era. That’ll do.
Worst trade: Acquired Ricardo Rincon from Pirates for Brian Giles (November 18, 1998)
Trading a hitter for a pitcher usually doesn’t work out too well for the team that acquires the pitcher. But trading a hitter for a relief pitcher? A specialized relief pitcher? That’s a recipe for disaster. And a disaster is what unfolded when the Indians dealt from a strength to make their bullpen marginally better. Rincon wasn’t terrible with Cleveland – he had a 3.73 ERA in 154 1/3 innings. But those 154 1/3 innings came over three and a half seasons – he topped out at 54 innings as a member of the Tribe. Plain and simple, he was a LOOGY – a guy who would come in, get lefties out, and then get his fistbumps in the dugout. A player like that has value, but GMs often place too much value on them.
And sure enough, John Hart put too much value on Rincon. He acquired him, straight up, from the Pirates for an outfielder named Brian Giles, who put together a .284/.391/.485 line in 1,033 plate appearances over 299 games with the Indians. Giles was moved so David Justice could move back into the outfield, opening up DH for players like Harold Baines, Richie Sexson (who also spelled Jim Thome at first and Justice in left), and Wil Cordero. A year later, Sexson would be in left field after Justice was dealt to the Yankees, in case you were curious about how ridiculous it was to trade Giles.
I’ve barely talked about Giles, because everyone knows what a star he became in Pittsburgh. In his brief five season tenure with the club, Giles hit an insane .308/.426/.591 with 165 homers and nearly 200 more walks than strikeouts. He made two All-Star teams, and received MVP votes in four seasons. The Pirates then sold incredibly high on Giles in 2003, dealing him to the Padres in an August trade for Jason Bay (who would the NL Rookie of the Year award in 2004) and Oliver Perez. If only the Pirates were able to get good returns for those two – they could have turned Rincon into even more stars instead of Xavier Nady, Brandon Moss (pre-breakout), Craig Hansen, and Andy LaRoche.
Colorado Rockies
Best trade: Acquired Carlos Gonzalez, Greg Smith, and Huston Street from Athletics for Matt Holliday (November 10, 2008)
Matt Holliday had a great career as a Rockie, there’s no denying that. He made three All-Star Teams, won three Silver Sluggers, and was the 2007 NL MVP runner-up. But everyone and their mother knew that Holliday would be leaving the Rockies as a free agent following the 2009 season. Colorado needed to trade him that winter, and they found a willing partner in Billy Beane.
And while the Rockies only got three players for Holliday, two of them would play key roles on their teams during the early part of this decade. Carlos Gonzalez has played all three outfield positions with the Rockies, and has effectively supplanted Holliday in their lineup. In six seasons with the club, he’s hit .300/.360/.540 with 132 homers and 106 stolen bases. He put together 20/20 seasons in each year from 2010 to 2013, picking up three Gold Gloves and two All-Star nods along the way. In 2010, Gonzalez won the NL batting title and finished third in MVP voting. He’s now a popular trade target thanks to his hefty contract and an injury history that is getting a little frightening. Greg Smith only tallied 39 innings for the Rockies, but Huston Street served as the club’s closer for three seasons before being traded to the Padres after the 2011 season.
As for Holliday? Well, he lasted only 93 games with Oakland before they traded him to the Cardinals, where he caught fire, signed a contract extension, and continued to play quite well. None of the three players the A’s got from St. Louis had much of an impact in the majors for the team.
Worst trade: Acquired Jeremy Guthrie from Orioles for Jason Hammel and Matt Lindstrom (February 6, 2012)
This might not definitely be the worst offseason trade Colorado has ever made, but recency bias is creeping into this article. Guthrie was awful with Colorado tossing 90 2/3 innings during the 2012 season and posting an unsightly 6.35 ERA. The Rockies traded him at midseason to the Royals, and his ERA dropped by three runs in the second half. He’s crossed the 200 inning mark in each of the last two seasons with Kansas City, and has been an effective (albeit unspectacular) starter for the club. The guy they traded Guthrie for that July was Jonathan Sanchez, who lasted only 11 1/3 innings in Denver. He allowed 13 runs, walked nine, and struck out nine during his brief tenure with the club.
Baltimore got good value out of their return from Guthrie, though the Rockies probably wouldn’t have gotten anything close to that level of production. In two seasons with the Orioles, Hammel had a 4.27 ERA in 257 1/3 innings. Injuries derailed the bulk of his time with the team, as he made just 43 starts over those two seasons. Lindstrom had a 2.72 ERA in 36 1/3 innings with the Orioles in 2012, and was traded to the Diamondbacks that August for Joe Saunders. Saunders pitched to a 3.63 ERA in 44 2/3 innings for the Orioles, and ended up getting the win in the team’s Wild Card game against the Rangers.
Detroit Tigers
Best trade: Acquired Miguel Cabrera and Dontrelle Willis from Marlins for Burke Badenhop, Frankie de la Cruz, Cameron Maybin, Andrew Miller, Mike Rabelo, and Dallas Trahen (December 4, 2007)
Miguel Cabrera was an all-world talent at the time of this trade, but was starting to get expensive. So when the opportunity came for the Marlins to sell high on him *and* dump the disgusting contract of Dontrelle Willis, they had to take it. Willis was a disaster with Detroit – he pitched to a 6.86 ERA in 101 innings over three seasons, and was paid a cool $29 million for that work.
I don’t think I need to doubt Cabrera’s accomplishments all that much. At the time of the deal, he was a 24-year old with four All-Star appearances, a pair of top five MVP finishes, 138 career homers, and a .313/.388/.542 line. He actually didn’t make the All-Star Team in either of his first two seasons with the Tigers, but hasn’t missed it in his five most recent years. He’s added three more top five MVP finishes to his ledger, and won the award in both 2012 and 2013. In 2012, he became the first player to win the Triple Crown since Carl Yastrzemski. He’s just 31, and is sitting on 390 homers with a .320/.396/.564 line. Needless to say, it really wouldn’t matter what the Tigers gave up in the deal when you get a player like that in return.
Worst trade: Acquired Juan Gonzalez, Danny Patterson, and Gregg Zaun from Rangers for Frank Catalanotto, Francisco Cordero, Bill Haselman, Gabe Kapler, Justin Thompson, and Alan Webb (November 2, 1999)
A historic flop could have turned into a legendary flop had Gonzalez accepted Detroit’s eight-year, $140 million contract offer after the trade. He declined it, and the Tigers ended up a lot better off. The former two-time AL MVP spent just one year in Detroit, and was a disappointment across the board. He played in just 115 games, smashing 22 homers and hitting a pedestrian (considering that it was 2000) .289/.337/.505. He signed a one-year deal for $10 million with the Indians, and was back to his old form. But that was Gonzalez’s swan song – he got a two-year, $24 million deal from the Rangers that winter, and played in just 152 games over those two seasons. He played just 33 games for the Royals in 2004, and his career was over at 35 after one at bat with Cleveland in 2005. For what it’s worth, he would have still had two years left under the offered contract when he retired.
Danny Patterson was actually a better performer with the Tigers than Gonzalez. He spent five seasons with the club, pitching to a 4.02 ERA in 183 2/3 innings. Gregg Zaun was a journeyman backup catcher, and was traded to the Royals during Spring Training.
The return that the Rangers got was essentially full of role players. Alan Webb never made it to the majors. Frank Catalanotto hit .305/.380/.470 over three years in Texas, playing all over the diamond. Francisco Cordero was a mainstay in the Rangers bullpen for years, tallying 397 innings with the team, notching a 3.45 ERA, and saving 117 games. He was traded to the Brewers as part of the Nelson Cruz/Carlos Lee deal. Bill Haselman served as an adequate backup catcher in Texas for three years. Former top prospect Gabe Kapler hit .280/.342/.433 in three seasons with the Rangers before winning a ring in 2004 with the Red Sox, becoming an awesome TV analyst, and later joining the Dodgers front office. Justin Thompson threw just 1 2/3 innings with the Rangers before his career ended.