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CLEVELAND - NOVEMBER 07:  Running back Peyton Hillis #40 and Alex Mack #55 of the Cleveland Browns celebrate after a touchdown against the New England Patriots at Cleveland Browns Stadium on November 7, 2010 in Cleveland, Ohio.  (Photo by Matt Sullivan/Ge
CLEVELAND - NOVEMBER 07: Running back Peyton Hillis #40 and Alex Mack #55 of the Cleveland Browns celebrate after a touchdown against the New England Patriots at Cleveland Browns Stadium on November 7, 2010 in Cleveland, Ohio. (Photo by Matt Sullivan/GeMatt Sullivan/Getty Images

Peyton Hillis for Brady Quinn and the 25 Worst Trades of Last 25 Years

Gabe ZaldivarNov 8, 2010

Peyton Hillis lit up the stat line again yesterday. Right about now, the Broncos could sure use his power, sure hands, and explosiveness. 

That fact got me thinking about the worst trades of my lifetime. Sometimes trades are necessary, even though what you may be trading is a valuable asset. These are just inexcusable. 

25. Jeff Bagwell To the Houston Astros

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HOUSTON - AUGUST 30:  Houston Astros hitting coach Jeff Bagwell #5 looks on from the dugout at Minute Maid Park during a game against the St. Louis Cardinals on August 30, 2010 in Houston, Texas.  (Photo by Bob Levey/Getty Images)
HOUSTON - AUGUST 30: Houston Astros hitting coach Jeff Bagwell #5 looks on from the dugout at Minute Maid Park during a game against the St. Louis Cardinals on August 30, 2010 in Houston, Texas. (Photo by Bob Levey/Getty Images)

Jeff Bagwell was a hot prospect in the Red Sox organization. It just so happens that there was no room for him in a talented infield. The Sox then chose to depart with him in exchange for the aging pitcher Larry Andersen. 

Bagwell would go on to become the face of the Astros organization until his retirement in 2005.

24. Chicago Bulls Trade Elton Brand

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LOS ANGELES, CA - APRIL 18:  Elton Brand #42 of the Los Angeles Clippers looks on against the New Orleans/Oklahoma City Hornets at Staples Center on April 18, 2007 in Los Angeles, California. NOTE TO USER: User expressly acknowledges and agrees that, by d
LOS ANGELES, CA - APRIL 18: Elton Brand #42 of the Los Angeles Clippers looks on against the New Orleans/Oklahoma City Hornets at Staples Center on April 18, 2007 in Los Angeles, California. NOTE TO USER: User expressly acknowledges and agrees that, by d

Mark this one as a rare occasion where the Clippers got the best of another team. They traded away Tyson Chandler and his empty uniform to the Bulls in exchange for Elton Brand. 

Brand would have his best years as a Clipper, making the All-Star team in 2002 and 2006. 

23. Giants Trade Pitching For Catching, Lose Big

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CHICAGO - SEPTEMBER 14: A.J. Pierzynski #12 of the Chicago White Sox argues a called third strike with umpire Brian O'Nora during a game against the Minnesota Twins at U.S. Cellular Field on September 14, 2010 in Chicago, Illinois. (Photo by Jonathan Dani
CHICAGO - SEPTEMBER 14: A.J. Pierzynski #12 of the Chicago White Sox argues a called third strike with umpire Brian O'Nora during a game against the Minnesota Twins at U.S. Cellular Field on September 14, 2010 in Chicago, Illinois. (Photo by Jonathan Dani

In 2003, the San Francisco Giants needed hitting and a catcher. They thought they found both in Twins backstop AJ Pierzynski. Being flush with pitching, the Giants traded away Joe Nathan and Francisco Liriano. 

Nathan went on to become one of the best closers in baseball and Liriano is still a pitcher with upside. AJ Pierzynski only spent one year with the Giants before declaring for free agency.  

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22. Kevin Garnett Becomes a Celtic

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CLEVELAND - OCTOBER 27:  Kevin Garnett #5 of the Boston Celtics looks to pass to a teammate next to Antawn Jamison #4 of the Cleveland Cavaliers at Quicken Loans Arena on October 27, 2010 in Cleveland, Ohio.  (Photo by Gregory Shamus/Getty Images)
CLEVELAND - OCTOBER 27: Kevin Garnett #5 of the Boston Celtics looks to pass to a teammate next to Antawn Jamison #4 of the Cleveland Cavaliers at Quicken Loans Arena on October 27, 2010 in Cleveland, Ohio. (Photo by Gregory Shamus/Getty Images)

Kevin Garnett was seemingly the only thing keeping the Minnesota Timberwolves relevant. In hindsight, they should have made more of an effort to hold on to their franchise player. 

Instead, they shipped off the unhappy camper to Boston in 2007 for Al Jefferson, Ryan Gomes, Sebastian Telfair, Gerald Green, Theo Ratliff, cash and Boston's 2009 first-round draft pick. All of that went to Minnesota and they still have nothing to show for it. 

21. Seattle Misses Out On Talent

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3 Sep 2000:  Pitcher Heathcliff Slocumb #58 of the San Diego Padres winds up for the pitch during the game against the Pittsburgh Pirates at Qualcomm Stadium in San Diego, California.  The Pardes defeated the Pirates 8-6.Mandatory Credit: Jeff Gross  /All
3 Sep 2000: Pitcher Heathcliff Slocumb #58 of the San Diego Padres winds up for the pitch during the game against the Pittsburgh Pirates at Qualcomm Stadium in San Diego, California. The Pardes defeated the Pirates 8-6.Mandatory Credit: Jeff Gross /All

The Mariners committed one of the bigger gaffs in baseball history. In 1997, they traded away Derek Lowe and Jason Varitek to the Red Sox for Heathcliff Slocumb. 

Varitek went on to become a sturdy catcher for the eventual World Series champions. Derek Lowe turned in some fine years for the Red Sox as well. Meanwhile, Slocumb continued to give up home runs until his retirement in 2000.

20. Don Nelson Does Something Right

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The draft in 1998 was a time of great success for then head coach of the Mavericks, Don Nelson. On draft day, he sent Robert Traylor to the Bucks for Dirk Nowitzki and Pat Garrity to the Suns for Steve Nash. 

They could have been the greatest tandem in all of the NBA, if the Mavericks hadn't ruined it by trading away Nash a few years later. 

19. Peyton Hillis For Brady Quinn

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CLEVELAND - NOVEMBER 07:  Running back Peyton Hillis #40 of the Cleveland Browns runs the ball against the New England Patriots at Cleveland Browns Stadium on November 7, 2010 in Cleveland, Ohio.  (Photo by Matt Sullivan/Getty Images)
CLEVELAND - NOVEMBER 07: Running back Peyton Hillis #40 of the Cleveland Browns runs the ball against the New England Patriots at Cleveland Browns Stadium on November 7, 2010 in Cleveland, Ohio. (Photo by Matt Sullivan/Getty Images)

Hillis was the victim of a new coach taking over in Denver. He had a promising future with Mike Shanahan until the Denver brass fired him in favor of Josh McDaniels. McDaniels had a new plan and it did not include Hillis. 

He was traded in the off season for backup Brady Quinn. Quinn is still a backup and Hillis is lighting it up for the Browns. 

18. Scottie Pippen To the Bulls

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28 Apr 2001:  Olden Polynice #0 of the Utah Jazz in game three of round one in the NBA playoffs against the Dallas Mavericks at Reunion Arena in Dallas, Texas.  The Mavericks won 94-91. DIGITAL IMAGE.  Mandatory Credit:  Ronald Martinez/Allsport
28 Apr 2001: Olden Polynice #0 of the Utah Jazz in game three of round one in the NBA playoffs against the Dallas Mavericks at Reunion Arena in Dallas, Texas. The Mavericks won 94-91. DIGITAL IMAGE. Mandatory Credit: Ronald Martinez/Allsport

Scottie Pippen was selected fifth overall by the Seattle Supersonics. They then took that jewel and shipped it off to Chicago for Olden Polynice. 

Pippen went on to become one of the 50 greatest NBA players to ever play and Olden Polynice just sort of got old. 

17. The Great One Leaves Edmonton

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The good people of Edmonton went from the highest of highs to the lowest of lows in one off season. After winning the Stanley Cup in 1988, the Oilers shipped Wayne Gretzky and friends Marty McSorley and Mike Krushelnyski to Los Angeles in exchange for Jimmy Carson, Martin Gelinas, and $15 million in cash.

The move has since been rumored to be all about money, which Oilers owner Peter Pocklington was bleeding on his other ventures. 

16. Orioles Trade Away Curt Schilling and Steve Finley

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BOSTON - APRIL 08: Curt Schilling #38 of the Boston Red Sox heads out on to the field to get his 2007 World Series Championship Ring before the game the Detroit Tigers on April 8,2008 during Opening Day at Fenway Park in Boston, Massachusetts. (Photo by E
BOSTON - APRIL 08: Curt Schilling #38 of the Boston Red Sox heads out on to the field to get his 2007 World Series Championship Ring before the game the Detroit Tigers on April 8,2008 during Opening Day at Fenway Park in Boston, Massachusetts. (Photo by E

In 1990, the Baltimore Orioles traded away Curt Schilling and Steve Finley for Glen Davis. The Orioles let go of a future Hall of Fame pitcher and an outfielder that was a perennial All-Star in the late nineties. 

Schilling will never complain, as he has gone on to win three World Series Championships in his career and the Orioles are the laughingstock of the American League East. 

15. John Smoltz to Atlanta

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ATLANTA - JUNE 26:  Pitcher John Smoltz #29 of the Boston Red Sox enjoys a laugh during pregame warmups before facing the Atlanta Braves at Turner Field on June 26, 2009 in Atlanta, Georgia.  (Photo by Kevin C. Cox/Getty Images)
ATLANTA - JUNE 26: Pitcher John Smoltz #29 of the Boston Red Sox enjoys a laugh during pregame warmups before facing the Atlanta Braves at Turner Field on June 26, 2009 in Atlanta, Georgia. (Photo by Kevin C. Cox/Getty Images)

In 1987, the Detroit Tigers needed pitching. Enter the ironic tag, as the Tigers sent John Smoltz and his eventual 200 wins to the Braves in exchange for 36 year old pitcher Doyle Alexander. 

14. Pedro Martinez For Delino DeShields

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Being a Dodgers fan, this one stings for me. 

The Dodgers fell into the thinking that small pitchers cannot maintain a long and healthy career. They also needed a second baseman. So they traded Martinez to the Expos in 1994 for Delino DeShields. Pedro Martinez would go on to have a brilliant, Hall of Fame caliber career. 

13. Jerome Bettis Becomes the Bus

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TAMPA, FL - FEBRUARY 01:  NBC football analyast and former Pittsburgh Steelers running back Jerome Bettis walks on the field during warm ups for Super Bowl XLIII between the Arizona Cardinals and the Pittsburgh Steelers on February 1, 2009 at Raymond Jame
TAMPA, FL - FEBRUARY 01: NBC football analyast and former Pittsburgh Steelers running back Jerome Bettis walks on the field during warm ups for Super Bowl XLIII between the Arizona Cardinals and the Pittsburgh Steelers on February 1, 2009 at Raymond Jame

The Rams had themselves the great battering ram. Jerome Bettis would mow down defenses like they were paper. 

He fell out of favor with the coaching staff and was traded to the Steelers for picks. He went on to become "the Bus" and continued to mow down defenses, this time in the AFC. 

12. 76ers Part With Charles Barkley

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Charles Barkley was the franchise player for the Philadelphia 76ers. He had come upon controversial times and Philadelphia soon had enough. In 1992, they decided that it was best to part with the superstar. They traded him to the Phoenix Suns for Jeff Hornacek, Tim Perry and Andrew Lang. 

Hornacek was the only player with decent talent and he was on the wrong side of his career. Barkley would reemerge as an exciting player on the fast tempo Suns team of the nineties. 

11. Herschel Walker Leaves Dallas

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CANTON, OH - AUGUST 7: Emmitt Smith poses with his bust during the 2010 Pro Football Hall of Fame Enshrinement Ceremony at the Pro Football Hall of Fame Field at Fawcett Stadium on August 7, 2010 in Canton, Ohio. (Photo by Joe Robbins/Getty Images)
CANTON, OH - AUGUST 7: Emmitt Smith poses with his bust during the 2010 Pro Football Hall of Fame Enshrinement Ceremony at the Pro Football Hall of Fame Field at Fawcett Stadium on August 7, 2010 in Canton, Ohio. (Photo by Joe Robbins/Getty Images)

Herschel Walker leaving the Cowboys should have been the start of a sad tale for the Cowboys. Instead, it was the Vikings, who traded away a multitude of draft picks, that lost here. 

With those picks, the Cowboys would draft Emmitt Smith and the core of the Super Bowl championship teams in the 1990's.

10. Marshall Faulk to Rams

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ST. LOUIS - DECEMBER 18:  Marshall Faulk #28 of the St. Louis Rams looks to get by Sheldon Brown #24 of the Philadelphia Eagles  at the Edward Jones Dome on December 18, 2005 in St. Louis, Missouri.  (Photo by Dilip Vishwanat/Getty Images)
ST. LOUIS - DECEMBER 18: Marshall Faulk #28 of the St. Louis Rams looks to get by Sheldon Brown #24 of the Philadelphia Eagles at the Edward Jones Dome on December 18, 2005 in St. Louis, Missouri. (Photo by Dilip Vishwanat/Getty Images)

Marshall Faulk was making waves in Indianapolis. He was rumored to be holding out for more money, a practice that is widely used today. The Colts owner had seen enough and traded the running back to the Rams for second and fifth round picks.

Faulk went on to become a pivotal piece for the "greatest show on turf", winning a Super Bowl in 2000. 

9. Allen Iverson For Chauncey Billups

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AUBURN HILLS, MI - MAY 3:  Chauncey Billups #1 of the Detroit Pistons is defended by Allen Iverson #3 of the Philadelphia 76ers in Game five of the Eastern Conference Quarterfinals during the 2005 NBA Playoffs at The Palace of Auburn Hills on May 3, 2005
AUBURN HILLS, MI - MAY 3: Chauncey Billups #1 of the Detroit Pistons is defended by Allen Iverson #3 of the Philadelphia 76ers in Game five of the Eastern Conference Quarterfinals during the 2005 NBA Playoffs at The Palace of Auburn Hills on May 3, 2005

Allen Iverson is a handful. That is the lesson Joe Dumars found out in 2006 when he traded for the All-Star. He sent his leader Chauncey Billups to the Nuggets for A.I.

The Nuggets thrived under Billups' leadership. They are still a contender in the west. Meanwhile, Iverson is playing in Turkey. As soon as he landed in Detroit, he feuded with the coaching staff and refused to play off the bench. 

This is one I am sure Joe Dumars would like back. 

8. Grant Hill To The Magic

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ORLANDO, FL - NOVEMBER 01:  Grant Hill #33 of the Orlando Magic is introduced prior to taking on the Chicago Bulls on November 1, 2006 at TD Waterhouse Centre in Orlando, Florida.  NOTE TO USER: User expressly acknowledges and agrees that, by downloading
ORLANDO, FL - NOVEMBER 01: Grant Hill #33 of the Orlando Magic is introduced prior to taking on the Chicago Bulls on November 1, 2006 at TD Waterhouse Centre in Orlando, Florida. NOTE TO USER: User expressly acknowledges and agrees that, by downloading

At the time, the Magic were thought to get the better of the deal in the trade that sent Grant Hill to Orlando for Chucky Atkins and Ben Wallace. Instead, Wallace would be the cornerstone for the successful Pistons team that won the championship in 2004. 

The Magic were supposed to have gotten a superstar, but they received a player that would play very few games for the organization due to injuries.

7. Ditka Sells the Farm

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MINNEAPOLIS - SEPTEMBER 19:  Ricky Williams #34 of the Miami Dolphins carries the ball during the game against the Minnesota Vikings on September 19, 2010 at Hubert H. Humphrey Metrodome in Minneapolis, Minnesota.  (Photo by Jamie Squire/Getty Images)
MINNEAPOLIS - SEPTEMBER 19: Ricky Williams #34 of the Miami Dolphins carries the ball during the game against the Minnesota Vikings on September 19, 2010 at Hubert H. Humphrey Metrodome in Minneapolis, Minnesota. (Photo by Jamie Squire/Getty Images)

There was a lot of hype surrounding highly prized recruit Ricky Williams at draft time in 1999. It may be why Mike Ditka traded away all of his draft picks just to secure the rights to the running back. 

Williams impressed for the first year and then slipped into lethargy and marijuana use. He was eventually cut by the Saints and then relegated to the Canadian Football League. He has since reemerged as a force for the Dolphins. 

6. Pau Gasol To The Lakers

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SACRAMENTO, CA - NOVEMBER 03:  Kobe Bryant #24 and Pau Gasol #16 of the Los Angeles Lakers walk off the court for halftime after the Lakers made a last second shot against the Sacramento Kings at ARCO Arena on November 3, 2010 in Sacramento, California.
SACRAMENTO, CA - NOVEMBER 03: Kobe Bryant #24 and Pau Gasol #16 of the Los Angeles Lakers walk off the court for halftime after the Lakers made a last second shot against the Sacramento Kings at ARCO Arena on November 3, 2010 in Sacramento, California.

In 2008, the Lakers pulled a rabbit out of their hat. They sent small handed Kwame Brown, Javaris Crittenton, Aaron McKie, and the rights to Marc Gasol to Memphis for Pau Gasol. 

While Marc Gasol is an All-Star center in the making, Pau has gone on to win back to back championships with the Lakers. 

5. Sammy Sosa For George Bell

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OAKLAND, CA - JULY 18:   Sammy Sosa #21 of the Texas Rangers looks on against the Oakland Athletics  during a Major League Baseball game on July 18, 2007 at McAfee Coliseum in Oakland, California.  (Photo by Jed Jacobsohn/Getty Images)
OAKLAND, CA - JULY 18: Sammy Sosa #21 of the Texas Rangers looks on against the Oakland Athletics during a Major League Baseball game on July 18, 2007 at McAfee Coliseum in Oakland, California. (Photo by Jed Jacobsohn/Getty Images)

Let us forget that Sammy Sosa did an obscene amount of steroids once he became a Chicago Cub. He went from a quick footed slender outfielder into a behemoth slugger. 

The White Sox traded away the future home run hitter for George Bell in 1992. Bell retired the next year and Sosa went on to put butts in baseball seats in the great home run battle between him and Mark McGwire during the summer of 1998.

4. Brett Favre For Tony Smith

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In 1992, the Atlanta Falcons did not buy into Brett Favre being their number one quarterback. Atlanta head coach Jerry Glanville despised that they even had him on the roster. 

So the Falcons had no qualms about shipping him to the Packers for 19th overall pick Tony Smith. Brett Favre went on to have a pretty good career of retiring and un-retiring. 

3. Tampa Bay Buccaneers Miss Out On a Legend

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SAN FRANCISCO - OCTOBER 5: Former San Francisco 49ers quarterback Steve Young speaks during a ceremony to retire his number at halftime of the New England Patriots and the San Francisco 49ers NFL game on October 5, 2008 at Candlestick Park in San Francisc
SAN FRANCISCO - OCTOBER 5: Former San Francisco 49ers quarterback Steve Young speaks during a ceremony to retire his number at halftime of the New England Patriots and the San Francisco 49ers NFL game on October 5, 2008 at Candlestick Park in San Francisc

The Buccaneers were not sold on Steve Young. The Bucs had a young stud in Vinny Testaverde to take the snaps, so they parted with Steve Young. 

Young went on to back up Joe Montana until it was his turn to become a legendary quarterback. Young is one of the best ever to play the position, and Testaverde is, well, not. 

2. Vlade Divac For Kobe Bryant

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The Hornets needed a big man back in 1996. So when the Lakers came calling for their 13th overall pick for their starting center, the Hornets bit. Vlade Divac was a good player. He could pass and hit the 15 footer. There is no denying that he helped the Hornets for the couple of years that he was there. 

However, the fact that Kobe Bryant is one of the best NBA players ever makes this one a lopsided trade. It is possibly the worst in NBA history. 

1. Chargers Trade For Biggest Bust Ever

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24 Sep 2000:  Quarterback Ryan Leaf #16 of the San Diego Chargers passes the ball during the game against the Seattle Seahawks at Qualcomm Stadium in San Diego, California. The Seahawks defeated the Chargers 20-12.Mandatory Credit: Stephen Dunn  /Allsport
24 Sep 2000: Quarterback Ryan Leaf #16 of the San Diego Chargers passes the ball during the game against the Seattle Seahawks at Qualcomm Stadium in San Diego, California. The Seahawks defeated the Chargers 20-12.Mandatory Credit: Stephen Dunn /Allsport

The Chargers had the third pick of the 1998 draft. They did not want to miss out on the highly touted Ryan Leaf, so they traded two first round picks, a second round pick, and four time Pro Bowler Eric Metcalf to the Arizona Cardinals for Ryan Leaf. 

Never mind that the Cardinals had a QB, or that the Colts, who were first to pick, were taking Peyton Manning. This is the worst trade because it was unnecessary and it lead to one of the biggest busts the NFL has ever seen in Ryan Leaf. 

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