The 20 Worst Trades in Sports History

When your team makes a major trade, the first question that always comes to mind is: Will this help my team or end up a disaster? Will it one day be considered one of the worst trades in sports history?

From the Seattle Sonics' decision to trade Scottie Pippin for Oden Polynice—which led to Michael Jordan's six NBA Championships—to Boston's sale of Babe Ruth for a musical, terrible trades can change the history of sports.

Here is a ranking of the worst trades in sports history.  

Note: Check out this video for even more commentary on the worst baseball, basketball, football, and hockey trades in history. 

20. A.J. Pierzynski to San Francisco for Joe Nathan and Francisco Liriano

The Terms

The San Francisco Giants acquired catcher A.J. Pierzynski for future Hall of Famer Joe Nathan and Francisco Liriano.

Why It's Awful

The mercurial Pierzynski was terrible in San Francisco and eventually made it back to the American League Central, where he helped the Chicago White Sox win the 2005 World Series. Meanwhile, Joe Nathan became one of the best closers of all time in Minnesota.  

19. Mariners Trade Jason Varitek and Derek Lowe to Boston

The Terms

The Seattle Mariners trade Jason Varitek and Derek Lowe to Boston for Heathcliff Slocumb.

Why It's Awful

Slocumb quickly deteriorated and was out of Seattle by 1998. Boston gained two future All-Stars and key cogs in their 2004 team, which won the franchise's first World Series in 86 years.

Plus, isn't it amazing that the Mariners had Varitek, Lowe, Ken Griffey Jr. and Randy Johnson in their organization and never reached the World Series?  

18. Mark McGwire Traded to the Cardinals

The Terms

Mark McGwire traded from the Oakland Athletics to the St. Louis Cardinals for bit-piece pitchers T.J. Matthews, Blake Stein and Eric Ludwick.

Why it's Awful

None of those pitchers ever amounted to anything in Oakland while McGwire went on to catapult the Cardinals to national media attention during his compelling (and steroid-fueled) race for home run records in 1998.

Unfortunately, McGwire also left no titles and a major steroid stain on the organization, which lowers this trades' place on the all-time "worst" list.  

17. Randy Johnson Traded to the Seattle Mariners

The Terms

The Montreal Expos traded pitchers Randy Johnson, Gene Harris and Brian Holman to the Seattle Mariners for pitchers Mark Langston and Mike Campbell in 1989.

Why It's Awful

The Expos franchise died because they never held onto stars for more than a few years, and the excitement completely died.

What if the franchise had held on to Johnson or Pedro Martinez? We will never know, which is why the franchise is now located in Washington D.C.  

16. Pedro Martinez Traded to the Montreal Expos

The Terms

Pedro Martinez was traded to Montreal for second baseman Delino DeShields.

Why It's Awful

The Dodgers knew Martinez's potential but decided to deal him anyway. He became a Hall of Fame pitcher, first with the Expos, where he won the 1997 Cy Young, then more famously with the Boston Red Sox.

The Dodgers, who had the money to lock up Martinez for the prime of his career, earned no benefit at all from his immense talent.  

15. John Smoltz Traded to Atlanta for Doyle Alexander

The Terms

In 1987, the Detroit Tigers sent young prospect John Smoltz to the Atlanta Braves for Doyle Alexander.

Why It's Awful

In fairness, Alexander's performance helped Detroit reach the postseason. But he collapsed in playoff play and was never the same, retiring in 1989. Smoltz partnered with Greg Maddux and Tom Glavine as part of the greatest pitching trio in a generation.  

14. Eric Lindros to Philadelphia

The Terms

After a post-draft holdout, Quebec traded Lindros to the Philadelphia Flyers for Peter Forsberg, Ron Hextall, Chris Simon, Mike Ricci, Kerry Huffman, Steve Duchesne, two first-round picks and $15 million.

Why It's Awful

Lindros was supposed to be a future superstar but was so prone to concussions that he barely got on the ice. He became a talk show punch-line, while Forsberg won the Hart Trophy and Quebec (after moving to Colorado) rode its trade haul to two NHL Stanley Cups.  

13. Nolan Ryan Dealt to the California Angels

The Terms

The New York Mets dealt Nolan Ryan, along with pitcher Don Rose, outfielder Leroy Stanton and catcher Francisco Estrada to California for shortstop Jim Fregosi.

Why It's Awful

Ryan went on to have a Hall of Fame career as the King of Strikeouts. The Mets, who got less than a season of (poor) productivity out of Fregosi, languished in baseball purgatory for the better part of the decade.  

12. Jeff Bagwell to Houston for Larry Anderson

The Terms

In 1990, the Red Sox sent young future star Jeff Bagwell to Houston for reliever Larry Andersen.  

Why It's Awful

The Bagwell trade is one of the most lopsided trades in sports history. Boston got 22 innings of middling play out of Andersen while Bagwell went on to become a future Hall of Famer, the 1991 Rookie of the Year, and the 1994 National League MVP.  

11. Shoeless Joe Jackson to Cleveland for Bris Lord

The Terms

Ten games into his career, Jackson was shipped from the Philadelphia Athletics to Cleveland in exchange for journeyman Bris Lord.

Why It's Awful

Jackson went on to bat .350 for his career and was one of the best defensive outfielders in baseball history. He was also embroiled in the infamous 1919 Black Sox scandal, though re-examination of his .400 batting average with no errors in the 1919 World Series suggests he was likely innocent.  

10. Scottie Pippen Traded to the Chicago Bulls

The Terms

The Seattle Sonics traded Pippen, the fifth pick in the draft, to Chicago in exchange for the eighth pick, center Olden Polynice, a second-round pick and the option to switch first-round picks in 1989.

Why It's Awful

Polynice was a classic draft bust. By contrast, Pippen was the perfect complement to Michael Jordan, and the duo won six titles and changed the course of NBA history.  

9. Marshall Faulk to St. Louis for Second- and Fifth-Round Picks

The Terms

The Indianapolis Colts trade Marshall Faulk to the St. Louis Rams for second- and fifth-round draft picks.

Why It's Awful

Faulk took the trade as motivation and went on to become the centerpiece of St. Louis' "Greatest Show on Turf" offense with quarterback Kurt Warner, which won the 1999 NFL Super Bowl and got back to the big game in 2001.

Even worse, can you imagine the Colts' offense with Peyton Manning and Marshall Faulk leading the way?  

8. Julius Irving Is Sold to Philadelphia

The Terms

Roy Boe, the owner of the Long Island Nets, sold Dr. J to Philadelphia for $3 million.

Why It's Awful

Boe received no players or assets in return for Irving, who went on to become an 11-time All-Star and one of the best NBA small forwards of all time. Dr. J also put Philadelphia on the map as an NBA city, while the Nets were so unpopular after the trade that season ticket holders sued...and won!

7. John Elway to Denver for Mark Herrmann

The Terms

After drafting him No. 1 overall in the 1983 NFL draft, the Baltimore Colts traded John Elway to the Denver Broncos for Mark Herrmann, Chris Hinton and a first-round pick.

Why It's Awful

Elway was a can't-miss prospect who everyone knew would become a star. Similar to Andrew Luck and Peyton Manning, nearly every team wanted to draft him. The Colts won—but then Elway refused to play for them. This was the era of low draft bonuses and the USFL, so Elway's threat to play professional baseball was not meaningless.  

However, the fact that Baltimore only got Herrmann, a well-below average quarterback, and a first-round pick for a player of Elway's caliber still makes this one of the worst trades in history.  

Consider: The St. Louis Rams got more than double that haul this year, and they didn't even give Washington the rights to the best quarterback in the draft!

6. Robert Parish and Kevin McHale to the Boston Celtics for Draft Selections

The Terms

Boston Celtics trade the first and 13th overall selections for Robert Parish and Golden State's draft pick.

Why It's Awful

Everyone knew Parish was going to be a great player, and it is never a good idea to trade a young franchise center. The Celtics also turned Golden State's pick into Kevin McHale, and combined with Larry Bird to form the first Big Three in NBA History. 

5. Herschel Walker to the Minnesota Vikings

The Terms

The Vikings acquired Walker from the Dallas Cowboys in exchange for five players, a first-round selection, and six other draft choices.

Why It's Awful

Walker was fresh off two Pro-Bowl seasons, but he was aging—and running backs almost never age well in the NFL.

Walker never had a 1,000-yard season for the Vikings, while the Cowboys turned two of those picks into Hall of Famers Rod Woodson and Emmitt Smith and rode the trades' haul to three Super Bowl titles in the 1990s. 

4. Brett Favre to Green Bay for a First-Round Pick

The Terms

The Atlanta Falcons sent rookie Brett Favre to the Green Bay Packers for a first-round pick.

Why It's Awful

The Falcons never gave Favre much of a shot...and lived to regret it. He went on to become a Packers legend, winning the NFL's consecutive starts "Iron Man award," three NFL MVPs, and a Super Bowl along the way.

3. Kobe Bryant to Los Angeles for Vlade Divac

The Terms

The day before the draft, Charlotte shipped out its 13th overall draft pick to the Lakers in exchange for aging center Vlade Divac.

Why It's Awful

The Lakers turned that pick, which was part of the very deep 1996 NBA draft, into Kobe Bryant. Bryant has now won five NBA Championships and is the greatest player (along with Magic Johnson) in Lakers history. 

2. Bill Russell Traded to the Boston Celtics

The Terms

St. Louis Hawks trade Bill Russell to Boston for Ed Macauley and Cliff Hagan in 1956.

Why It's Awful

Russell went on to become the best NBA center of all time. He led the Celtics to a record 11 NBA titles (for one player) and made Boston the most storied franchise in basketball.  

1. Babe Ruth for a Musical

The Terms

Boston Red Sox trade future baseball god Babe Ruth for $100,000 and a $300,000 loan to finance the No, No, Nanette musical.  

Why It's Awful

Quite simply the worst deal in the history of sports.

Red Sox owner Harry Frazee dealt Ruth to the archival New York Yankees and watched them dominate in the World Series for the next 20 years while his own team won absolutely nothing.

How could anything be worse?