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The Most Regrettable Sports Trades Ever

Nick DimengoNov 11, 2014

Although no athlete ever wants to be the one getting traded, sometimes, it's actually the best thing that can happen for their career.

And when one does occur, the hope is that the teams involved will come out relatively even, with all sides involved happy with the decision they made.

It's too bad that doesn't always happen, though, as there have been more than a few that have been unequal, with certain teams getting less than they hoped for after pulling the trigger in an acquisition.

So which ones have been the most regrettable in sports? I've picked a few for you to debate.

James Harden to Houston Rockets

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Trade Details: James Harden traded from Oklahoma City Thunder to Houston Rockets for Kevin Martin and Jeremy Lamb, two first-round picks and a second-round pick.

Following the Oklahoma City Thunder reaching the NBA Finals in 2012, the team decided that, due to future financial restrictions, it needed to trade away its super-sub, James Harden.

So, that's exactly what it did, trading him to the Houston Rockets the day before the 2012-13 season tipped-off for decent pieces, but not of All-Star caliber like Harden.

After earning the league's Sixth Man of the Year Award that season, Harden had star potential and was searching for a starting role but wasn't going to get the love in OKC. And while the Thunder have had great seasons since Harden was sent packing, with the injuries to Kevin Durant, Russell Westbrook and the demand for a Big Three to win an NBA title, I bet the team wishes it would have made it work.

Steve Young to San Francisco 49ers

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Trade Details: Steve Young from Tampa Bay Buccaneers to San Francisco 49ers for second- and fourth-round draft picks.

Teams typically don't just give up on quarterbacks after just 19 career starts—especially when the talent around the player isn't up to par.

Unfortunately for the Tampa Bay Buccaneers in 1987, they decided the Steve Young era should come to an end, trading the future Hall of Famer to the San Francisco 49ers for just second- and fourth-round picks.

Sure, Young went a paltry 3-16 while leading the Bucs offense in his first two seasons in the league but, eventually, went on to take over the starting gig in San Fran, replaced the beloved Joe Montana and set a Super Bowl record by tossing six touchdown passes in his only appearance as a starter in the win.

All that for just a few draft picks? Yeah, I bet the leaders in Tampa Bay are still kicking themselves over this one.

Pedro Martinez to Montreal Expos

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Trade Details: Pedro Martinez from Los Angeles Dodgers to Montreal Expos for Delino DeShields.

Lasting just 67 games and three starts with the Los Angeles Dodgers in limited time, the team, ridiculously, gave up on some guy named Pedro Martinez prior to the 1994 season.

Packing his bags for the Montreal Expos, Pedro went 11-5 with a 3.42 in the strike-shortened season and went on to pitch for another 16 seasons following the trade, earning three Cy Young Awards, finishing with just one losing season and, arguably, becoming the most dominating pitcher of his era.

I'm sure the Dodgers would have really liked him doing all of that in sunny L.A. looking back now—especially since they just got an average player in Delino DeShields in return.

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Bill Russell to Boston Celtics

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Trade Details: Bill Russell traded from St. Louis Hawks to Boston Celtics for Ed Macauley.

On paper, the trade of Bill Russell to the Boston Celtics in 1956 isn't really as lopsided as some of the other ones I have on this list, but the impact was greater than just numbers.

Sure, the guy Russell got exchanged for, Ed Macauley, finds himself in the Hall of Fame and enjoyed three great seasons for the Hawks, but he never had the impact Russell did.

I mean, the guy is widely considered to be the greatest winner in the history of sports, earning 11 total NBA titles during his playing days and getting the NBA Finals MVP award named after him.

Brett Favre to Green Bay Packers

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Trade Details: Brett Favre traded from Atlanta Falcons to Green Bay Packers for a first-round pick.

Much like the aforementioned trade of Steve Young from the Tampa Bay Buccaneers to the San Francisco 49ers, former quarterback Brett Favre probably didn't get the patience he deserved.

Playing in just two games and tossing just four passes and two interceptions, the Atlanta Falcons figured the former second-rounder wasn't worth keeping around, with the team shipping the gunslinger to the Green Bay Packers to, allegedly, help sober him up.

All Favre did was win three straight league MVPs from 1995-97, take the Packers to back-to-back Super Bowl appearances—with one win—and break nearly every individual passing mark by the time he called it quits.

Would the Falcons have wanted that kind of production? Yeah, I'm guessing they would have.

Nolan Ryan to California Angels

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Trade Details: Nolan Ryan, among others, traded from New York Mets to California Angels for Jim Fregosi.

Hoping to bolster the left side of their infield, the New York Mets made the bold decision to send a young, 24-year-old flame-throwing pitcher named Nolan Ryan to the California Angels for former All-Star Jim Fregosi before the 1972 season.

Yeah, that didn't turn out to be too smart.

Rather than upgrade the Mets, Fregosi battled injuries, playing in just 146 total games for the Angels before they shipped him off to the Texas Rangers in the middle of the 1973 season.

Nolan Ryan, though? He not only won 19 games for the Halos in his first season with the team, but eventually went on to strike out more batters than anyone else in MLB history, tossed seven no-hitters and won 324 games over the course of a 27-year career.

Scottie Pippen to Chicago Bulls

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Trade Details: Scottie Pippen from the Seattle Sonics to Chicago Bulls for Olden Polynice and the option to swap first-round picks in 1989.

Any time a future Hall of Famer gets traded for, what turned out to be, nothing but a journeyman, I would think that the team who traded away the star regrets the move.

For the Seattle Supersonics, they're the team that is probably kicking itself with the move to ship its 1987 No. 5 pick, Scottie Pippen, to the Chicago Bulls in exchange for the No. 8 pick, Olden Polynice, helping set up the best sports dynasty of the '90s.

Paired up with Michael Jordan in Chicago, Pippen went on to win six NBA titles, be mentioned as one of the league's 50 best players and earn a Hall of Fame induction.

Polynice averaged just 7.8 points and 6.7 rebounds per game, never sniffing an All-Star Game or NBA championship.

Julius Erving to Philadelphia 76ers

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Trade Details: Julius Erving sold by New York Nets to Philadelphia 76ers for $3 million.

One of the most electric players the sport has ever seen, Hall of Famer Julius Erving had fans in awe of his incredible leaping and dunking ability during the '70s and '80s.

Making an All-Star Game in each one of his 16 professional seasons, Erving also won the NBA MVP Award in 1981 and led the Philadelphia 76ers to an NBA title in 1983.

The move allowed embattled New York Nets owner Roy Boe to collect $3 million but saw tremendous outcry from Nets season-ticket holders, who sued the team for a refund—and won—which ultimately set the stage for the team to move from Long Island to New Jersey.

Who knew that one player could affect a franchise so much?

*Ed. Note - The 76ers franchise has 3 NBA titles.

Marshall Faulk to St. Louis Rams

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Trade Details: Marshall Faulk traded from Indianapolis Colts to St. Louis Rams for second- and fifth-round draft picks.

A former No. 2 overall selection of the Indianapolis Colts back in 1994, the team's best player was traded to the St. Louis Rams prior to the 1999 season due to a few misunderstandings, which included some missed practices and the threat of, potentially, holding out for a new contract.

So what did the Rams get for giving up just a second- and fifth-rounder?

How about a future Hall of Famer who is in the top 10 on the league's all-time rushing list, who earned one league MVP, helped them reach two Super Bowls—winning one—and proved to redefine the running back position with his versatility both running and catching the ball.

Faulk's abilities would have been pretty nice to have with some guy under center name Peyton Manning for a long time, don't you think?

Frank Robinson to Baltimore Orioles

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Trade Details: Frank Robinson traded to Baltimore Orioles for Milt Pappas, Jack Baldschun and Dick Simpson.

Considered to be an, "old 30 years old," by former Cincinnati Reds general manager Bill DeWitt, the team split ways with former league MVP and then six-time All-Star Frank Robinson in 1965.

While the Reds did receive three players in return—who all turned out to be mediocre—Robinson had one of the best seasons ever during his first year with the Baltimore Orioles, winning the Triple Crown and his second MVP, leading the O's to a World Series title.

He would go on to win one more ring with Baltimore in 1970 and got inducted into the Hall of Fame in 1982.

It turns out that he wasn't as old as DeWitt had originally thought.

Kobe Bryant to Los Angeles Lakers

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Trade Details: Kobe Bryant from Charlotte Hornets to Los Angeles Lakers for Vlade Divac.

Is this the worst trade in NBA history? A case could very well be made seeing what the Los Angeles Lakers got when obtaining then high schooler Kobe Bryant in a trade for Vlade Divac in 1996.

Hoping to play for the Lakers, Bryant pretty much forced his way from the Charlotte Hornets, joining forces in Tinseltown with the recently acquired Shaquille O'Neal prior to his first season with the Lakers.

While Divac was a solid big man for years, there's no comparison with Kobe, as the Black Mamba has won five NBA titles, a league MVP and, although he has made a few selfish decisions in his career, is recognized as a top-10 player in NBA history.

Hey, at least Charlotte has Michael Jordan as its owner now, am I right?

Herschel Walker to the Minnesota Vikings

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Trade Details: Herschel Walker from Dallas Cowboys to Minnesota Vikings for multiple players and draft picks.

An absolute beast and a Heisman Trophy winner, former running back Herschel Walker had quite the reputation around the league as being a true difference-maker.

It's too bad his name is forever linked to the success of the team that traded him away rather than keep him, though.

That's what happened with the Dallas Cowboys, though, who shipped Walker off to the Minnesota Vikings back in 1989, which involved 18 players and multiple draft picks.

With Dallas eventually ending up with six of Minnesota's first- and second-round selections in the years following, the Boys used the picks on Emmitt Smith—otherwise known as the NFL's all-time leading rusher—and Darren Woodson, with others used to acquire other young players to build the core of a team that won three Super Bowls in the '90s.

As for Walker, he played just two-in-a-half years in Minnesota, never rushing for more than 825 yards.

Wayne Gretzky to Los Angeles Kings

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Trade Details: Wayne Gretzky traded from Edmonton Oilers to Los Angeles Kings for Martin Gelinas, Jimmy Carson, three first-round picks and $15 million.

The guy is known strictly as "The Great One," so is there any doubt the Edmonton Oilers regret trading away the NHL's best, Wayne Gretzky, to the Los Angeles Kings back in 1988?

Hours after winning his fourth Stanley Cup in five seasons with Edmonton, news broke that Gretzky would be playing in Hollywood the next time he took the ice—much to the shock of everyone.

The trade wasn't finalized until August, and, although Gretzky cried in an exit press conference, "The Trade" went through, sending Oilers fans and the entire country of Canada into a frenzy.

He may not have won another title in his career, but Gretzky became the greatest player ever—something every Canadian wishes would have happened in his home country.

John Elway to Denver Broncos

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Trade Details: John Elway from Baltimore Colts to Denver Broncos for Mark Hermann, Chris Hinton and 1984 first-round draft pick.

Refusing to play for the Baltimore Colts, 1983's No. 1 overall pick John Elway found himself as a member of the Denver Broncos, instead, traded for quarterback Mark Hermann, offensive tackle Chris Hinton and a first-round pick in the 1984 draft.

Oh, boy, was that a bad move.

Elway became an absolute legend in the Mile High City, where he won a then NFL record 148 games as a starter, appeared in five Super Bowls—winning two of them—and was inducted into the Hall of Fame in 2004.

He now leads Denver's front office, enjoying great success since taking over in 2011 as the executive vice president of football operations.

The other players involved in the swap had a few good years, but, come on, not anywhere close to that of Elway's career.

Babe Ruth to the New York Yankees

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Trade Details: Babe Ruth sold by Boston Red Sox to New York Yankees for $100,000.

When an entire franchise had a certain curse named after the trading/selling of a guy that lasts 86 seasons long, how can't it be the most regrettable trade in sports history?

After a six-year career with the Boston Red Sox from 1914-19, Red Sox owner Harry Frazee sold the greatest player in MLB history to the hated New York Yankees for $100,000—along with a $300,000 loan—back in 1920 to help finance the musical "No, No, Nanette."

All Ruth did was hit 665 home runs in Yankee pinstripes, finishing his career with a then MLB-record 714 and winning seven World Series titles in the Bronx.

The Sox and their fans lived through frustrated losses year-after-year, before finally breaking the "Curse of the Bambino" with their 2004 title.

Still, even after two championships since, the looming decision to trade away the best player the game has ever seen is forever linked between these two bitter rivals.

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