10 Most Bizarre Trades in Sports History

Oct 17th, 2011

A cleverly conceived trade can make a general manager’s career and launch a middling team into a new stratosphere of competitiveness. The Herschel Walker trade, for example, also known as "The Great Train Robbery," involved 18 players, the most effective of which were procured in the draft by the Cowboys. Of course, the Cowboys won three Super Bowls in the ’90s, thanks, in part, to Emmitt Smith, Darren Woodson, and Alvin Harper. On the less conventional side, the Pats obtained Bill Belichick from the Jets in exchange for draft picks, setting up their 2000s dynasty. The following trades are more like the latter — those weird ones that made you think "is that really possible?" and realize that there’s more to being a GM than merely plugging players into a trade simulator.

  1. Indians trade manager Joe Gordon to Tigers for manager Jimmy Dykes (1960)

    Baseball’s original version of "Flash" Gordon is regarded as one of the greatest second basemen of all time, winning five World Series titles during his Hall of Fame career. After he retired, he worked his way up to manager of the Indians, but his new job was made more difficult as he feuded with general manager Frank Lane, who often second-guessed his decisions. In 1959, Gordon was fired and rehired, leading up to his trade for Jimmy Dykes, the first transaction of its kind, during the 1960 season. He managed just 57 games for the Tigers, leaving them for the Kansas City Athletics following the season.

  2. Athletics trade manager Chuck Tanner to Pirates for catcher Manny Sanguillen (1977)

    Both Tanner and Sanguillen were accomplished at their respective positions. Tanner won Manager of the Year in 1972 when his White Sox pushed the vaunted A’s to the limit during the regular season, ultimately succumbing to a second place finish. Sanguillen earned three All-Star appearances and was an instrumental member of the Pirates’ 1971 World Series title-winning team. A year after their trade, Sanguillen was reacquired by the Pirates and assisted Tanner in securing his only World Series title on the "We Are Family" squad.

  3. Mariners trade manager Lou Piniella to Devil Rays for outfielder Randy Winn (2002)

    Ready to return home to the Florida Gulf Coast, an aging Piniella was warm to the idea of being traded from rainy Seattle to sunny Florida to manage the Rays. In return, the Mariners received Randy Winn, who was named to his only All-Star game in 2002. Two years removed from guiding the Mariners to a 116-46 record — tied for the most wins ever in a single season — Piniella received criticism when the team fizzled out in the playoffs. He endured three seasons in which his team lost 90 games or more as he was tasked with building the Rays into a winner. He departed after the 2005 season, critical of the front office’s lack of commitment to fielding a competitive squad.

  4. White Sox trade manager Ozzie Guillen to Marlins for two minor leaguers (2011)

    It took just eight years, a period in which he won a World Series title, for the always volatile Ozzie Guillen to wear out his welcome with the White Sox. His contentious relationship with general manager Ken Williams had been well-documented, and change seemed to be forthcoming regardless of the circumstances. As talks of a contract extension deteriorated, he was released from his position with the understanding that the team would receive compensation if he manages in 2012. The Marlins pounced on the opportunity, enabling Guillen to work where he keeps his offseason home.

  5. Patriots trade Bill Parcells to Jets for 1999 first-round draft pick, 1998 second-round pick, 1997 third-and fourth-round picks, and a $300,000 donation to the Patriots’ charitable foundation (1997)

    While in New England, Parcells’ famously once said "They want you to cook the dinner; at least they ought to let you shop for some of the groceries." Discontent over his lack of say in personnel matters, he sought to leave the Patriots after the 1997 season, but his contract prevented it. The moribund Jets, determined to secure the services of a proven winner, attempted to work their way around the impediment by hiring Bill Belichick as head coach and Parcells as an adviser. Recognizing the festering confusion and anger, Commissioner Paul Tagliabue oversaw the arrangement of the blockbuster trade that placated both sides.

  6. Jets trade Bill Belichick, 2001 fifth-round draft pick, and 2002 seventh-round draft pick to Jets for 2000 first-round draft pick, 2001 fourth-round draft pick, and 2002 seventh-round draft pick (2000)

    As it turned out, Belichick continued to serve as Parcells’ top assistant and defensive coordinator during Tuna’s stint with the Jets from 1997 to 1999. When Parcells retired, Belichick served as the Jets’ head coach for one day before resigning during his introductory press conference and subsequently accepting the same position with the Patriots. Because he was still under contract with the Jets, the Patriots were forced to provide compensation, which ended up being draft picks.

  7. Raiders trade Jon Gruden to Buccaneers for 2002 first-and second-round draft picks, 2003 first-round draft pick, 2004 second-round draft pick, and $8 million (2002)

    Al Davis certainly isn’t known for doing things by the book, and the manner in which he orchestrated Gruden’s departure is no exception. The Bucs were in desperate need of someone who could propel them to the Super Bowl after the firing of Tony Dungy, a move that was questioned by many in the NFL community and media. After being rejected by Bill Parcells, they turned their sights to Gruden. Davis initially refused to allow him to negotiate, but later relented and settled for a nice compensation package. Both teams seemed to benefit, as they met in Super Bowl XXXVII. Gruden’s Bucs won 48-21.

  8. Jets trade Herm Edwards to Chiefs for 2006 fourth-round draft pick (2006)

    In four seasons with the Jets, Edwards guided the team to three playoff appearances, but sank into hot water when he oversaw a miserable 4-12 season in 2005. Undeterred, the Chiefs proceeded pursue Edwards anyway. In an effort to secure a contract extension, Edwards embraced the attention, accelerating his eventual departure from New York. Emotionally, Jets owner Woody Johnson reached a point of no return, and allowed his front office to negotiate a deal with the Chiefs. Edwards tallied an underwhelming 15-33 record in three seasons in Kansas City.

  9. Heat trade Stan Van Gundy to Magic for 2007 second-round pick and 2008 second-round pick (2007)

    Despite being essentially run out of town by Pat Riley as the Heat struggled to meet lofty expectations, Van Gundy was viewed as a hot coaching commodity. The Magic, fresh off of the quick hiring and resignation of Florida Gators coach Billy Donovan, wanted a big name, and therefore offered the position to Van Gundy. He accepted, but the Heat didn’t want to give him up to their instate rival for nothing, demanding compensation in return. Two years later, the Magic reached the Finals while the Heat were in the process of clearing cap space for a big 2010 offseason.

  10. ABC trades broadcaster Al Michaels to NBC for Oswald the Lucky Rabbit, Ryder Cup matches, and Olympics highlights (2006)

    Believe it or not, the most bizarre trade in football history involved an Emmy Award-winning sportscaster and a Disney character. When NBC Sports secured the rights to Sunday Night Football, which essentially became the "game of the week" in place of Monday Night Football, chairman Dick Ebersol wanted an A-list crew — Michaels and John Madden, who previously worked on MNF, were considered the best tandem in the business. Michaels initially opted to continue calling MNF games for ESPN, but later asked to be allowed to move to NBC. The two networks struck up a deal centered on Oswald the Lucky Rabbit — who was developed by Walt Disney — enabling him to settle in to his rightful home.