Sports trades were all the rage this week with the NFL’s trade deadline passing on Tuesday afternoon with not many big names on the move or really anything shocking at all.
Recently we saw another blockbuster trade in the NBA when guard James Harden was traded from the Philadelphia 76ers to the Los Angeles Clippers to join a few other future Hall of Famers.
But Harden is past his prime. For there to be a truly shocking trade in sports right now, it would have to include someone at the top of their game like Shohei Ohtani in MLB, who recently signed with the Dodgers. That wasn’t a trade but the top offshore sportsbooks offered odds on which would be his next team.
This got us thinking about the most shocking trades in sports history, and we came up with a top 5 list of the moves that will forever live in infamy.
5 Ricky Williams
- New Orleans Saints Trade Entire Draft Class for RB (1999)
While NFL running backs in today’s game are fighting for fair pay, it was not that long ago that the position was held in such high regard that a team would do something as foolish as trading an entire draft class for a talented college running back.
But it happened in 1999 when Mike Ditka, the coach of the New Orleans Saints, traded his team’s whole draft class to move up from the No. 12 pick to the No. 5 pick to select Texas running back Ricky Williams. The Saints had already traded their 2nd-round pick that year, but they still sent the other 6 picks in 1999 to the Washington Redskins.
In total, the Saints gave up 8 draft picks, including a 1st-round pick in 2000 that was the No. 2 overall pick in the draft, to select Williams, who was not even the first running back off the draft board in 1999. The Indianapolis Colts drafted Edgerrin James with the No. 4 pick and he went on to make the Hall of Fame while Williams has not.
It was the first time in NFL history that a team made only one draft selection in an entire draft class. It led to a memorable cover photo for an issue of ESPN The Magazine where Ditka and Williams posed as bride and groom with Williams wearing a wedding dress and the caption reading “For better or worse.”
The Saints finished 3-13 in 1999 and Ditka was fired after a single season with Williams as the running back. It should be noted that the Saints did win their first playoff game in franchise history in 2000, but Williams was inactive for that game with an injury that kept him out of the final 6 games of the regular season too. He returned for the divisional round playoff game and carried the ball 6 times for 14 yards in a 34-16 loss against Minnesota.
Williams played one more season in New Orleans before he was traded to the Dolphins in 2002 where he went on to more success in a career cut short by an early retirement and an affinity for marijuana, a banned substance by the NFL during Williams’ career.
With what teams now know about the value of draft picks and the replaceability of running backs, you will never see a trade like this again.
4 Kareem Abdul-Jabbar
- Milwaukee Bucks to Los Angeles Lakers (1975)
Before the internet, basketball fans and writers argued between the greatness of Wilt Chamberlain and Bill Russell. Today, that argument is about LeBron James or Michael Jordan for the greatest of all time. But in between those eras, Kareem Abdul-Jabbar, formerly Lew Alcinder, was the greatest basketball player in the world.
Kareem won 6 championships, 6 MVP awards, and he held the NBA’s all-time scoring record from 1984 until 2023 when LeBron finally broke it. Throw in his outstanding college basketball career at UCLA where he led the Bruins to 3 straight championships, and it is a wonder why Abdul-Jabbar does not get more support for being the best to ever take the court.
But it was a trade that sent Abdul-Jabbar on the path to more greatness with the Lakers. The Milwaukee Bucks made him the No. 1 pick in the 1969 draft, and Kareem delivered with 6 straight All-Star seasons, 3 MVP awards, 2 scoring titles, and 1 NBA championship.
But after the Bucks were only 38-44 and missed the playoffs in the 1974-75 season, they listened to their star’s request and traded him to Los Angeles. The compensation was not the greatest as the Bucks only received Elmore Smith, Brian Winters (2-time All-Star selection), Dave Meyers, Junior Bridgeman, and some cash in return for Kareem.
Abdul-Jabbar immediately won the next 2 MVP awards in Los Angeles, but the 5 championships did not come until the 1980s when the team added Magic Johnson to create one of the best dynasties in NBA history. But Kareem was the Captain of those teams and cemented his legacy as one of the game’s greatest scorers and winners.
The Bucks did not win another championship until 2021 after they found another special talent in Giannis Antetokounmpo.
3 Herschel Walker
- Dallas Cowboys to Minnesota Vikings (1989)
The Herschel Walker trade in October 1989 is still the largest player trade in NFL history. At the end of the day, the trade involved 18 players and draft picks.
The background is that Walker, who was a star player in the USFL too, was a 27-year-old running back for the Cowboys who made the Pro Bowl with 1,514 rushing yards in 1988. He was considered the team’s best player in a tough transition period for Dallas as it fired Hall of Fame coach Tom Landry and replaced him with college coaching sensation Jimmy Johnson in 1989.
Expectations were low for Dallas, which started 0-5 with Walker only averaging 3.0 yards per carry and 49.2 rushing yards per game. He was an above-average pass catcher too, and that gave him extra value compared to other running backs at the time.
In an era where workhorse backs were king, and the Cowboys had such little on the roster to feel good about, people were shocked when Dallas dealt Walker to the Minnesota Vikings, a playoff-caliber team that felt it was a running back away from the Super Bowl.
Well, Walker led the Vikings in rushing despite only playing in 11 games for them in 1989, but they were destroyed 41-13 in the first playoff game against San Francisco, the eventual champion that year. Walker only lasted 2 more seasons in Minnesota before he was off to the Eagles, and the Vikings never won a playoff game with him.
That was the disappointing Minnesota side of things. The impact on Dallas was massive. Despite suffering through a 1-15 season in 1989, the trade was worth it for all the draft capital the Cowboys fleeced the Vikings for.
The trade had some conditional picks attached to it where the Cowboys would keep those picks in future drafts if they cut the veterans they received from Minnesota (Jesse Solomon, David Howard, Issiac Holt, and Alex Stewart) before February 1, 1990. The Vikings assumed Johnson would keep those players and that they would only owe the Cowboys 3 picks in the 1990 draft, including picks in the 1st and 2nd rounds.
But the Cowboys cut those players and were able to obtain 1st-round picks in 1991 and 1992, and picks in the 2nd and 3rd rounds in 1992. In the end, the Cowboys used these draft picks to add very important players such as Emmitt Smith, Russell Maryland, Clayton Holmes, Kevin Smith, and Darren Woodson.
The Cowboys used this trade to build a dynasty, and by 1991, they were back in the playoffs. In 1992, they won the Super Bowl behind Johnson and his draft picks, then they repeated in 1993. Johnson left the Cowboys, but the cupboard was still so full that even Barry Switzer won owner Jerry Jones his 3rd Super Bowl in the 1995 season.
You might think Minnesota’s disastrous trade for Walker would have scared teams away from trading a boatload of draft picks for a running back, but clearly, the 1999 Saints (Ricky Williams) did not learn anything from this historic trade.
With how easily teams replace running backs in the NFL, it is shocking that there have still been so many bad trades involving the position. Not only did we see it at the top of our list with the 1999 Saints and Ricky Williams, but the 2013 Colts also traded for Cleveland bust Trent Richardson in a regrettable move in Year 2 of the Andrew Luck era.
2 Babe Ruth
- Boston Red Sox to New York Yankees (1919)
It would not be a complete history lesson without going back over 100 years to the day when baseball’s most legendary star was traded for cash to kick off the greatest rivalry in the history of America’s pastime.
At 24 years old, Babe Ruth was already a star for the Boston Red Sox, whom he helped win 3 championships as the premiere franchise in baseball. After starting out as a pitcher, he was just emerging as the game’s greatest slugger when he hit a record 29 home runs in the 1919 season.
But in December 1919, shocking news broke that the Red Sox traded Ruth to the New York Yankees for cash considerations totaling $100,000, the richest contract (by a wide margin) to any ballplayer at the time.
Why would Boston trade such a superstar like Ruth just as he was hitting his prime? Reportedly, he wanted too much money, and the Red Sox had just wrapped up a season where they finished 66-71-1, good for 6th place despite Ruth’s home runs. He also was transitioning away from pitching to becoming a hitter.
But the trade backfired so bad it became known as The Curse of the Bambino. Behind Ruth’s legendary, record-setting home run hitting, the Yankees turned into the most successful team in baseball while the Red Sox did not win another World Series until 2004, an 86-year drought. This also led to the Yankees-Red Sox rivalry becoming the biggest one in baseball and maybe in all American team sports.
1 Wayne Gretzky
- Edmonton Oilers to Los Angeles Kings (1988)
There have been countless trades in the history of sports, but only one has been nicknamed “The Trade” and it is our No. 1 choice for the most shocking trade of all time.
While most great players eventually change teams, it often comes later in their careers when they are near the end like Tom Brady going to Tampa Bay or Jerry Rice to the Raiders.
In hockey, when you think of Gordie Howe, you think of the Detroit Red Wings where he played every year from ages 18-42. Mario Lemieux played all 17 seasons of his Hall of Fame career with the Pittsburgh Penguins, and Sidney Crosby looks to do the same in his 19th season.
But you might think Wayne Gretzky, the Great One himself, is a player who would have lasted more than 9 seasons with the Edmonton Oilers where he had his most success. In Edmonton, Gretzky set records for goals and assists that will likely never be broken. He also won the Hart Memorial Trophy (MVP) a stunning 8 years in a row in 1980-87.
Gretzky’s game also translated well to the postseason where he smashed records and helped the Oilers to 4 championships in a 5-year span. But legend has it that just 2 hours after Gretzky’s 4th championship win in 1988, his father informed him that the team was trading him, a secret he kept from Gretzky for months so he would not get upset.
Gretzky, 27, was undergoing trade discussions while on his honeymoon. Eventually, in August 1988, a deal was struck with the Los Angeles Kings, who gave up 2 players, 3 1st-round picks, and $15 million in cash.
The Trade sent shockwaves in the sport of hockey as the game’s greatest player was leaving his roots in Canada to join a West Coast team in America that had little success in the expansion-era NHL.
The Oilers, now led by Mark Messier, were able to win a 5th championship in the 1989-90 season, but you have to wonder what the final number would have been had Gretzky stayed with that core group in Edmonton.
Gretzky also had an immediate impact on the Kings, winning the MVP award for the final time in his 1st season with LA in 1988-89. Gretzky was able to lead the Kings to the Stanely Cup Finals in the 1992-93 season, but they lost in 5 games to the Montreal Canadiens.
In the end, Edmonton was better with Gretzky, and Gretzky was better with Edmonton. But the trade to the Kings did have a huge impact on the NHL and hockey’s popularity in the states.
With Gretzky playing in LA, people were tuning into games more to see the Great One in action. By the 1993-94 season, the NHL increased from 21 to 26 teams with another round of expansion to take advantage of unconventional hockey markets in Florida (Florida Panthers, Tampa Bay Lightning) and California (San Jose Sharks, Anaheim Ducks).
The Trade proves that even the best of the best can be moved in their prime. But with everything on our list happening in the 20th century before social media, it seems unlikely that a team could get away with dealing an all-time great at the top of their game in today’s leagues.
