Top 10 Worst Trades in Sports History

Since the inception of professional sports leagues, teams have engaged in the act of trading players and personnel with each other. Trades are executed for numerous reasons, such as the hopes of a new player improving a team, dumping contracts to save money, or gaining assets through acquiring rising star players or draft picks.

In an ideal and equal world, both teams should receive exactly what they bargain for in a trade. But, it doesn’t always end up like that. Just as many trades leave teams distraught as they do satisfied. Some trades ended so horrendously, they’re still talked about by their teams’ fan bases to this day.

10: The Cleveland Browns trade numerous draft picks to the Minnesota Vikings

Cleveland.com

The Cleveland Browns were in the middle of a historically horrendous stretch of losing when the 2012 Draft rolled around. Feeling desperate to find an impact player in the draft, the Browns initiated a trade of draft picks with the Minnesota Vikings.

The Vikings gave the Browns the third overall pick, while the Browns gave up the fourth overall pick, and their fourth, fifth, and seventh round picks. With their pick, the Browns selected Alabama running back Trent Richardson. Richardson had just ended an illustrious career with the Crimson Tide, winning two national titles and finishing third in the Heisman Trophy voting in his final year.

However, Richardson’s time in Cleveland was uneventful, lasting barely one season. Richardson hasn’t played in the NFL since 2016. The Vikings, on the other hand, drafted offensive tackle Matt Kalil, who would become a Pro Bowler.

9: Patrick Roy being traded from the Montreal Canadians to the Colorado Avalanche

Colorado Hockey Now

To hockey fans, Patrick Roy needs no introduction.

Roy tallied up a career never seen by a goalie before or since, making 11 All-Star appearances, winning the Conn Smythe trophy for best player in the playoffs three times, and winning the Vezina trophy for best goalie in the NHL three times. This occurred over 19 seasons, culminating in a Hockey Hall of Fame election in 2006.

Roy started his career with the Montreal Canadians, playing there from 1984 to 1996. During his time in Montreal, Roy helped with winning two Stanley Cups in 1986 and 1993. Roy and the Canadians were poised to rule the NHL for some time. However, four games into the 1995-96 season, the Canadians made a coaching change, hiring Roy’s former teammate, Mario Tremblay.

Roy still had animosity for Tremblay going back to their time as teammates. This reached a boiling point halfway through the season when Tremblay left Roy in net to let up 9 goals in an 11-1 loss to the Detroit Red Wings. After the game, Roy demanded to be let go from the Canadians.

Four days later, Roy was traded along with team captain Mike Keane to the Colorado Avalanche for Jocelyn Thibault, Martin Ručinský, and Andrei Kovalenko. That same season, Roy, Keane, and the Avalanche would win the Stanley Cup. Roy would also win one more with Colorado in 2001. As for the Canadians, they have not seen the same success, only making the conference finals twice since the trade.

8: Lou Brock being traded from the Chicago Cubs to the St. Louis Cardinals

iamCubsessed

Lou Brock is known as being one of the greatest outfielders and base stealers in the history of Major League Baseball. He finished his career with 938 stolen bases, a record at the time of his retirement. He was also a member of the legendary 3,000 hits club.

Yet, in 1964, Brock was still considered an up-and-comer with the Chicago Cubs. That year, Brock was in his fourth season in the big leagues, and even though the Cubs were happy with the speed he provided, they were also frustrated with his slow development.

Feeling that they needed to add to their bullpen, the Cubs traded Brock, along with Jack Spring and Paul Toth, to the Cardinals for pitchers Ernie Broglio, Bobby Shantz, and outfielder Doug Clemens. Brock had almost an immediate impact with the Cardinals, helping them win a World Series title that same season.

Brock’s potential came to fruition, winning another World Series in 1967, as well as racking up six All-Star appearances. Brock left a lasting impact on the Cardinals’ organization, who retired his number 20. He was elected to Baseball Hall of Fame in 1985. The Cubs, on the other hand, received little help from the players they received for Brock and company, and wouldn’t win a World Series until 2016.

7: Pedro Martinez is traded from the Los Angeles Dodgers to the Montreal Expos

FanSided

Pedro Martinez was one of the most dominant pitchers during MLB’s Steroid Era in the late 1990s and early 2000s. Although he had a physically smaller stature of 5-foot-11, he stood as a giant on the mound.

Martinez’s dominance wasn’t immediately recognized while he was with his first team, the Los Angeles Dodgers. In his second season in the majors in 1993, Martinez was used as a setup man, winning 10 games and posting a 2.91 ERA, as well as leading all National League relievers in innings pitched.

Heading into the 1994 season, the Dodgers were desperate for a second baseman. They decided to ship Martinez to the Montreal Expos in exchange for proven middle infielder Delino DeShields. While DeShields was serviceable for the Dodgers, Martinez was dominant for the Expos. He would make two All-Star teams with Montreal, as well as winning a Cy Young award as the National League’s best pitcher in 1997. Martinez’s career would continue to skyrocket, making six more All-Star teams, winning two more Cy Young awards, and helping the Red Sox win their first World Series title in 86 years in 2004.

6: Steve Young is traded from the Tampa Bay Buccaneers to the San Francisco 49ers

FOX Sports

After a frustrating tenure in the short-lived USFL, Steve Young decided to try playing in the NFL, signing with the Tampa Bay Buccaneers.

In the two seasons Young was on the team, the Bucs went a combined 4-28, including a 3-16 record with Young starting. In the 1987 Draft, Tampa Bay drafted University of Miami quarterback Vinny Testaverde. They considered Young a bust, and they traded him to the San Francisco 49ers to back up Joe Montana.

Young would be second string behind Montana for four seasons, including two Super Bowl-winning campaigns, before earning his chance to start. Young would take full advantage, earning seven Pro Bowl selections, MVPs in 1992 and 1994, and a Super Bowl victory in 1994. Young was a member of the 2005 Pro Football Hall of Fame class.

Testaverde had a solid career in the NFL, spanning nearly 20 years, but did very little with Tampa Bay. The Buccaneers would struggle until their Super Bowl 37 victory fifteen years later.

5: Kevin Garnett and Paul Pierce go to the Brooklyn Nets; the Boston Celtics receive numerous draft picks

NBC Sports

Kevin Garnett and Paul Pierce are considered two of the best players to ever play in the NBA. Garnett was already an MVP when he was traded to the Boston Celtics before the 2007-2008 season to join Pierce and fellow all-time great Ray Allen.

The trio would work extremely well together, winning the NBA championship that year and making a second appearance in the NBA Finals in 2010. However, as the years progressed, the trio of stars became older. The beginning of the end in Boston occurred when Allen signed a contract with the Miami Heat before the 2012-2013 season as a bench player to join another trio of all-time greats in LeBron James, Dwyane Wade, and Chris Bosh.

The writing was on the wall that a rebuild was inevitable, so the Celtics began shopping around to find teams that would be interested in Garnett and Pierce. After the 2012-2013 season, they found that team with the Brooklyn Nets. That offseason, the Nets were looking to create a team that could compete with the Heat and others in the Eastern Conference.

They had already acquired stars Deron Williams, Joe Johnson, and Brook Lopez, and they hired Hall of Famer Jason Kidd as their head coach. They felt Boston’s dynamic duo could put them over the top. The Celtics would trade Garnett and Pierce, along with Jason Terry, to the Nets for four future first-round picks and five players.

The Garnett and Pierce eras didn’t last long in Brooklyn. The season after being eliminated in the second round of the playoffs, Garnett was traded to the Minnesota Timberwolves, where he had begun his career. Pierce would leave to sign with the Washington Wizards.

Although none of the players the Celtics received in the trade turned out to do anything important, the draft picks they received turned into promising young stars Jaylen Brown and Jayson Tatum, who have both been named all stars before the age of 25 and are pivotal for the future of the Celtics.

4: Brett Favre is traded from the Atlanta Falcons to the Green Bay Packers

UPROXX

Brett Favre is one of the greatest quarterbacks in NFL history. He is an 11-time Pro Bowler, a three-time MVP, and a Super Bowl champion. Yet, the team that originally drafted him, the Atlanta Falcons, didn’t see him that way.

Favre was picked 33rd overall in the 1991 NFL Draft. Falcons head coach Jerry Glanville disapproved greatly of the pick. Favre would only attempt four passes while with the Falcons. That offseason, Favre was traded to the Green Bay Packers for the 19th overall pick in the 1992 Draft. That pick would turn into running back Tony Smith, who would only play two seasons with the Falcons. Favre, on the other hand, would play a hall-of-fame career in Green Bay.

3: Kobe Bryant traded from the Charlotte Hornets to the Los Angeles Lakers

ClutchPoints

Going into the 1996 NBA Draft, high school player Kobe Bryant was seen as one of the best prospects. In the first round, with the 13th overall pick, the Charlotte Hornets would pick the 18-year-old Bryant. However, Bryant was not on Charlotte’s radar.

Instead, it was the Los Angeles Lakers, who liked what they saw from Bryant during his pre-draft workouts, that wanted him. In addition, the Lakers were looking to trade center Vlade Divac to clear up salary cap space. Charlotte was looking for a center, and agreed the night before the draft to trade the rights to their pick to the Lakers. Thus, The Hornets drafted Bryant and immediately traded him to the Lakers for Divac.

Divac would play with the Hornets for two years before signing with the Sacramento Kings in July of 1998. The late Bryant, on the other hand, would go on to play the rest of his career with the Lakers, being an All Star 18 times, winning an MVP in 2008, capturing five NBA titles, and taking home two NBA Finals MVPs. He had two numbers retired by the Lakers (8 and 24), and he was elected into the Basketball Hall of Fame in 2021.

2: Herschel Walker is traded from the Dallas Cowboys to the Minnesota Vikings for basically everybody

ESPN

Herschel Walker is considered one of the greatest players in college football history. In his three seasons at Georgia, Walker was a three-time all-American and a Heisman Trophy winner. It’s not surprising that Walker was highly coveted.

After a season in the short-lived USFL, Walker signed with the Dallas Cowboys, the NFL team that owned the rights to sign the running back. With Dallas, Walker was a two-time Pro Bowler, surpassing 1,500 rushing yards in 1988. Looking to find their franchise player, the Minnesota Vikings offered up five players and six draft picks, which the Cowboys happily accepted.

Walker would have a steady career in the NFL, but only lasted two-and-a-half years with the Vikings. The Cowboys would take those draft picks to draft talented players, including Hall of Fame running back Emmitt Smith. This led to three Super Bowls for Dallas in the early-to-mid 1990s.

1: Babe Ruth is sold from the Boston Red Sox to the New York Yankees

USA Today FTW

There is no other trade that could be number one on this list. This is the trade that led to a curse of a franchise. Babe Ruth signed with the Boston Red Sox in 1914. Primarily used as a pitcher, Ruth was dominant, winning 94 games in six years with the Red Sox, helping to win three World Series titles.

Near the end of his tenure, Ruth also emerged as a power hitter, which was extremely rare at that time in MLB’s history. After the 1919 season, Red Sox owner Harry Frazee decided to sell Ruth to the New York Yankees for 100,000 dollars. Legend has it that Frazee used the money to fund a show of Broadway, No No Nanette, which ended up failing.

The short-term and long-term effects of the trade resonated through the Red Sox, Yankees, and Major League Baseball. Ruth would go on to revolutionize hitting, setting the MLB single-season and career home run records that wouldn’t be broken for nearly forty years. He helped the Yankees win four World Series titles, and is considered by many to be the greatest player in history.

The Red Sox would suffer from the “Curse of the Bambino,” not winning another World Series until 2004, 86 years later. In that stretch, the Yankees would win 26 World Series titles.

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