Dating back to their move to Oakland in 1968 from Kansas City, the Athletics have made a number of trades intending to both contend for the playoffs as well as rebuild their farm system towards future contention.
Many of these trades have worked out well for the A's. Billy Beane, in particular, has been placed on a pedestal and heralded as one of the league's best general managers for his ability to identify talent and fleece other gm's of their top prospects and stars.
Beane's mentor, Sandy Alderson, also made a number of moves that helped the Athletics build their system into a contender.
Throughout the years there have been a number of moves that stand out as bad decisions. Whether it be because of injuries to the players acquired, or that the players who were shipped out of Oakland had sudden breakout seasons, the A's have seen some of their top talent perform well elsewhere while the players acquired were not nearly as productive.
The A's are in a position this season where they may need to make a trade before the deadline to bolster their offense and provide their pitching with the support necessary to make a deep run at the postseason for the first time since 2006. We all hope that if they do pull the trigger on a trade, it will be considered a successful trade and not wind up on a "worst-of" list down the road.
Here's a look at the worst trades in Oakland history, in my opinion. Please feel free to mention any trades you think I overlooked in the comments.
Roger Maris is best known as a New York Yankee. In fact he is best known as THE New York Yankee that broke Babe Ruth's single season home run record when he blasted 61 homers in 1961.
Just two seasons before though, he was playing for the Athletics in Kansas City.
On December 11, 1959 Maris was traded (with Joe DeMaestri and Kent Hadley) to the New York Yankees for Don Larsen, Hank Bauer, Norm Siebern and Marv Throneberry.
At the time it was not a bad return considering Maris had never hit more than 28 home runs in a season, and was around a .260 hitter.
Don Larsen went on to a 2-10 record however for the Athletics before being traded to the Chicago White Sox in 1961.
Hank Bauer was released by the Athletics in 1961, although he did serve as the team's manager in 1961 and 1962 in Kansas City, and again in 1969 in Oakland.
Maris would go on to hit over 200 home runs after leaving the Athletics though, including 100 in his first two full seasons after being traded to New York.
The trading of Reggie Jackson to the Baltimore Orioles in 1976 marked the beginning of Charlie Finley's dismantling of the A's World Series Three-peat dynasty.
Jackson was traded (with Ken Holtzman) to Baltimore Orioles for Don Baylor, Mike Torrez and Paul Mitchell.
Reggie would go on to play in eight more All Star games, and continue his drive towards the Hall of Fame with the New York Yankees and California Angels after his single season with the Orioles.
Reggie won three World Series with the A's, but he became "Mr. October" with the Yankees.
Don Baylor played a single season with the Oakland Athletics. He hit .247 and had 15 home runs for Oakland.
In 1976, Charlie Finley began dismantling his dynasty. He started with the trade of Reggie Jackson, but also tried to trade Rollie Fingers and Joe Rudi to the Boston Red Sox, and sell Vida Blue to the New York Yankees.
Rudi and Fingers suited up for the Red Sox for one game, but never played. Commissioner Bowie Kuhn refused to allow the deals to be completed and returned all three players to the Athletics.
Angry that the deals were overturned, Finley ordered his players sit out the following week's worth of games. The A's still managed a record of 87-74 and contended for their sixth straight AL West Division title, but finished two and a half games behind the Kansas City Royals and in second place.
Many A's fans believe had Finley not tried to sell and trade his players, the A's would have won their sixth straight division title.
Joe Rudi and Rollie Fingers would depart following the season via free agency. Vida Blue would leave the following year in 1977.
After stealing over 100 bases three times in his first five professional seasons, the A's traded Rickey Henderson to the New York Yankees following the 1984 season.
In return for Rickey and Bert Bradley the New York Yankees sent Stan Javier, Jay Howell, Jose Rijo, Eric Plunk and Tim Birtsas.
The huge package of prospects sent to the Athletics did provide production for the A's. Stan Javier would play a little over four seasons for the Athletics, and was part of the 1989 World Series Championship team, but he was never a huge part of the A's successes.
Jay Howell pitched three seasons for the Athletics and compiled a record of 15-18.
Jose Rijo went 17-22 for the Athletics in his three seasons before leaving for the Cincinnati Reds. Rijo would be a big part of the Reds team that would beat the Athletics in the 1990 World Series.
Although he was traded by Oakland in 1987 to the Reds, the A's received Dave Parker in return for Rijo, that trade does not rank as one of Oakland's worst despite Rijo's successes as a Red.
Meanwhile, Rickey would be an All Star all four seasons in New York, and would lead the American League in stolen bases three times, including 93 steals in 1988.
Rickey would be traded back to Oakland in 1989 and help lead the team to a four-game sweep of the San Francisco Giants to become World Series Champions.
This trade will probably be a bit of a controversial pick as a "worst" trade for many A's fans. Canseco has become a polarizing player since his days with the A's in the late '80's and early '90's, but there is no denying that he was an impact player back with the Oakland A's during his early career.
The trade that sent Canseco to the Texas Rangers in 1992 in return for Ruben Sierra, Bobby Witt and Jeff Russell seemed good at the time. Sierra was a power hitter that came with less distractions and baggage than Canseco and Bobby Witt was a solid starting pitcher.
The A's did go on to win 96 games in 1992, and played for the American League pennant. They lost in six games to the Toronto Blue Jays however, who had the A's over matched offensively. Had Canseco's bat still been in the A's lineup perhaps they would have faired better against the Jays and competed for another World Series title that year.
The following season was when the loss of Canseco was really felt though. The A's were only able to manage a record of 68-94 as Mark McGwire missed the majority of the season, and Canseco (who also missed the majority of the season) was helping the Rangers.
Canseco would go on to have an MVP-type season (11th in the voting) in the strike shortened 1994 season, belting 31 homers and 90 RBI in only 111 games.
Following his 52-homer campaign in 1996, Mark McGwire entered 1997 on a tear, threatening to challenge the single-season home run record set by Roger Maris.
Like Maris, McGwire would go on to break the record in another uniform instead of an Athletics one.
McGwire was set to become a free agent at the end of the 1997 season, and Oakland was not in contention, so they traded their slugger to the St. Louis Cardinals for Eric Ludwick, T.J. Mathews and Blake Stein.
Like Maris, who was traded by the A's in 1959 (two seasons before he would set the single season record), McGwire would break the record shortly after being traded to the Cardinals.
McGwire's record breaking season came the following year in 1998 when he smashed 70 balls over the fences in National League parks.
This trade only looks bad now because are forced to witness the production Nelson Cruz is providing to the division rival Texas Rangers.
Cruz had his breakout season for the Rangers in 2009, belting 33 home runs and driving in 76 RBI. He connected for 22 long balls last season while batting .318 for the American League Champion Rangers.
The A's received Keith Ginter in return for Nelson Cruz (and Justin Lehr). Ginter only played 51 games for the Athletics before his career ended. He batted just .161 with 3 home runs.
The A's were forced to trade Tim Hudson (as well as Mark Mulder) in 2005 due to budgetary concerns and to rebuild a weakened farm system.
Hudson was the leader of the A's "Big Three" and a key part of their string of postseason runs in the early 2000's. He was a fan favorite in Oakland, and although his trade was understandable due to the free agents losses we had suffered in past years with Jason Giambi and Miguel Tejada leaving for richer contracts, it was still a tough loss for A's fans to swallow.
What makes it tougher is Hudson's continued successes since the trade, while the players we got in return are long gone from Oakland, having never made any kind of impact with the team.
Oakland received Juan Cruz, Dan Meyer and Charles Thomas in return for Hudson.
Only Cruz is still in the Major Leagues, and he has never amounted to anything more than a steady middle reliever.
Andre Ethier, like Nelson Cruz, never played a game for the Oakland A's, yet his trade haunts Oakland fans.
Ethier was traded to Los Angeles in 2005 in exchange for Milton Bradley. Bradley helped the A's to the American League Championship series in 2006 against the Detroit Tigers, but his injury plagued season limited his effectiveness. He appeared in just 96 games for the Athletics in 2006.
In 2007 he made 19 appearances for the Athletics before having a run-in with general manager Billy Beane, who promptly shipped him to the San Diego Padres.
Andre Ethier has developed into an All-Star for the Dodgers since the trade. He finished sixth in MVP voting in 2009, and just recently had a 30-game hitting streak.
Ethier may not have had the same successes in Oakland, but the A's would have benefited from having a player of his caliber around the past few seasons as the offense has struggled without a presence such as him in the lineup.
Carlos Gonzalez was traded along with Huston Street and Greg Smith to the Colorado Rockies following the 2008 season for Matt Holliday.
Gonzalez was widely regarded by most A's fans as the future cornerstone of the franchise and lineup. A five-tool prospect who was only granted one season to prove himself in Oakland, he has developed into a MVP caliber player in his short time with the Rockies.
Gonzalez batted .336 with 34 homers and 117 RBI for the Rockies in 2010 while finishing third in MVP voting and winning his first Gold Glove.
At just 25 years old, the sky is still the limit for Gonzalez's potential impact on the Rockies lineup throughout his career. He will be an All-Star and impact player for the better part of the next decade, and A's fans will only be able to wonder "what-if"?
Matt Holliday never showed any interest in playing for Oakland in his half season with the Athletics. He was traded before the trade deadline to the St. Louis Cardinals for Brett Wallace.
Holliday caught fire for the Cardinals after his trade from Oakland, further annoying A's fans who were never in favor of the trade to begin with.
The only player acquired by the A's for Matt Holliday, Brett Wallace, was traded later that offseason to the Toronto Blue Jays for another prospect, Michael Taylor.
Taylor has gone from being a top prospect in the A's system, to practically falling off the radar with his sudden loss of power and inability to stay healthy.
If he rediscovers his abilities and turns out to be a productive member of the A's outfield for the next five to six seasons, then this trade still has the ability to be a decent swap for the A's.
Brett Wallace meanwhile was traded from the Blue Jays to the Houston Astros. Since joining the Astros, Wallace has looked like the hitting prospect the A's were hoping he would be when they acquired him from the Cardinals.
Wallace has been converted from a third baseman to first base, but he is currently hitting .349 for the Astros with a pair of home runs. The Athletics are currently lacking offense at first base from Daric Barton and would gladly welcome those production numbers from Wallace in their lineup.
Although this is not a win for the Blue Jays either, since they gave up on Wallace, this trade is not looking like a favorable one for the A's at this point.
We'll likely be revisiting this trade as early as next year to determine if this qualifies as one of the A's worst trades or not.