Ranking the 20 most lopsided trades in sports history: Which team pulled off the biggest robbery?

Most lopsided trades in sports history
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Ranking the 20 most lopsided trades in sports history: Which team pulled off the biggest robbery?

20. March 16, 1998: Chargers trade two first-rounders, a second-rounder and a player for the rights to the second-overall pick, used to draft Ryan Leaf

There are bad trade, and then there are bad trades followed by embarrassing draft decisions that lead to a lifetime of punchlines.

Not only did the Chargers elect to draft Ryan Leaf with the second overall selection in 1998 -- one pick after Peyton Manning -- but they traded up to get there. Notable players still on the board include Randy Moss, Charles Woodson, Hines Ward and Matt Hasselbeck, to name a few.


17. June 22, 1987: Sonics trade Scottie Pippen and a first-round pick to Bulls for Olden Polynice and two picks

In an attempt to trade back in the 1987 draft and acquire more assets, the Seattle Sonics dealt away Scottie Pippen, the fifth pick, for the eighth pick and several future choices. That eighth pick was Olden Polynice, who you probably have never heard of. Pippen went onto be one of the 1990's best players and Michael Jordan's second option on Bulls teams that won six championships. 


15. November 19, 1993: Dodgers trade Pedro Martinez to the Expos for Delino DeShields

It's safe to call this one a failure in judgement by the Dodgers. Trading Pedro Martinez after just three career starts is a bold move, but returning only Delino Deshields, who would leave Los Angeles after three seasons is a travesty. 

Pedro would win 219 games in his 18-year career, posting a pair of 300-strikeout seasons.


14. April 17, 1999: Redskins trade rights to Ricky Williams to New Orleans for eight draft picks

Mike Ditka was once given full control of the New Orleans Saints, and it didn't go so well. His first major transaction was trading his entire 1999 draft for Ricky Williams. Literally. All of their picks in the '99 draft, plus a first-rounder in 2000, which turned into LaVarr Arrington. Champ Bailey and Jon Jansen were other Pro Bowl results of the deal for Washington.

Ditka was out of the NFL after the 1999 season.


13. June 27, 2002: Indians trade Bartolo Colon and Tim Drew to Expos for Cliff Lee, Brandon Phillips, Grady Sizemore and Lee Stevens

Near the 2002 trade deadline, the Cleveland Indians were out of the race, and the Montreal Expos were desperate to make a splash that would resonate with the fanbase. The result: Montreal dealt three future all-stars for ace Bartolo Colon, who would leave the Expos in free agency after a half-season. The Expos would spend just two more years in Montreal.


12. November 22, 1988: Bucks trade Dirk Nowitzki and Pat Garrity to Mavericks for Robert Traylor

In hopes of beefing up with a big man, the Bucks traded the rights to slim, lengthy rookie Dirk Nowitzki on draft day, 1998. Nowitzki has gone on to become one of the most talented players of this generation, while Robert Traylor, whom they received for Nowitzki, spent two years in Milwaukee. 


5. February 11, 1992: Falcons trade Brett Favre to Packers for 17th-overall pick

After famously drafting "Brett Favor" in 1991, the Atlanta Falcons quickly gave up on the backup quarterback before ever appearing in a game. With a need at the position, the Green Bay Packers flipped their first-round pick for him the following year. He would go on to start 321 consecutive games including the playoffs—an NFL record—and brought a Super Bowl back to Lambeau Field.



Trades come into play in every professional sport. Some guesswork usually factors into the equation, as does a little bit of luck. But when the odds aren't in your favor? You end up in the history books -- for all the wrong reasons.

On the 40th anniversary of Kareem Abdul-Jabbar being shipped to the Los Angeles Lakers for relative peanuts, we've ranked the top 20 most lopsided swaps in sports history. Did the Milwaukee Bucks' misfortune top our list? Click through above and find out.

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