13. Houston Oilers Trade Steve Largent To Seattle Seahawks:
This trade was simply an outright robbery. Houston drafted Largent in the fourth round of the 1976 NFL draft, but they apparently thought so little of him that they were going to cut him. So Seattle took a chance on the receiver for the low cost of an eighth-round pick, and the rest is history.
Largent went on to become one of the best wide receivers in NFL history. He racked up insane numbers, with 819 receptions, 13,089 yards, and 100 touchdowns over the course of 14 years. It could be argued he’s the greatest player in the history of the Seattle Seahawks. Not bad for an eighth-round pick.
12. Oakland Raiders Trade Khalil Mack To Chicago Bears:
This head-scratching trade had many wondering if Oakland coach Jon Gruden had truly lost his marbles before his return in 2018. Pass rusher extraordinaire Mack was holding out for a huge contract extension heading into the season. Gruden apparently didn’t want to set the tone that he was going to cave to players’ salary demands, so instead of extending Mack, he traded him.
The Raiders shipped Mack and a second-round pick (along with a conditional fifth-rounder) to Chicago for a first-round pick in both the 2019 and 2020 drafts, along with third and sixth-round selections. In 2019, they turned that pick into running back Josh Jacobs from Alabama, who looks to be a promising prospect in the NFL. But Mack, like Cooper before him, is simply one of the best in the NFL at his position. Chicago promptly gave him the extension he wanted, and for good reason. Mack was voted one of the top three players in the NFL by his peers in 2019. You just don’t trade away generational pass rushers in their prime. Oakland’s recent track record on the defensive side of the ball shows why.
11. Saints Trade Entire Draft To Washington To Draft Ricky Williams:
This was a strange one that you’ll probably never see happen again. There’s a huge reason for it. In 1999, New Orleans Saints head coach Mike Ditka saw it fit to trade New Orleans’ entire draft, which consisted of eight picks, to the Washington Redskins. The trade moved New Orleans up to number five from number 12 in the first round so they could select Heisman-winning Texas running back Ricky Williams.
Williams himself wasn’t a bust. He may not have delivered numbers worthy of trading an entire draft for, but it’s tough to say any one player would. Overall, he was a very solid running back. But when Ditka was run out of town, it seemed the team no longer had very much allegiance for Williams either. They traded him to the Miami Dolphins in 2002, cutting loose a player who cost them a literal treasure trove of picks only three years prior. This was a dumb move even if Williams turned out to be a good NFL running back. It set the Saints franchise back multiple years.
10. St. Louis Rams Trade Jerome Bettis To Pittsburgh Steelers:
This one is just a mess looking back on it. Heading into the 1996 NFL season, the St. Louis Rams had drafted former Nebraska standout Lawrence Phillips with the No. 6 overall pick. They wanted to move their previous running back, the bruising Bettis, to fullback so Phillips could be the featured runner. But “The Bus” wasn’t on board with that. He wanted to stay at running back and continue carrying the ball. So the Rams sent Bettis and a third-round pick to the Pittsburgh Steelers for second and fourth-round picks.
Bettis was far from done. He rumbled to a ton of yards in Pittsburgh en route to a Hall of Fame career in the NFL. Phillips was soon out of the NFL, however, and eventually jailed for a host of violent arrests. He tragically committed suicide in prison. On a more positive note, Bettis won a Super Bowl in his native Detroit, capping off his great career with a storybook ending. It would never have happened if the Rams hadn’t made the huge mistake of siding with Phillips over Bettis.
9. Indianapolis Colts Trade Marshall Faulk To St. Louis Rams:
Former San Diego St. workhorse Faulk proved his skillset could translate to the NFL level in his early-career years with the Indianapolis Colts. So it was a bit of a head-scratcher that they sent Faulk to St. Louis for second and fifth-round picks.
That deal turned out to be an outright robbery, however, when St. Louis launched their infamous “Greatest Show On Turf” attack in 1999. Paired with quarterback Kurt Warner and wide receivers Isaac Bruce and Torry Holt, Faulk was a versatile weapon who racked up yards on the ground and through the air. It could be argued he set the blueprint for the versatile, dual-threat running backs of today. The Rams made up for their foolish trade of Bettis years earlier with this deal for Hall of Fame inductee Faulk.
8. Oakland Raiders Trade Randy Moss To New England Patriots:
Yes, the Raiders are up on the list again, and this isn’t the last one. But it’s one of the worst, as Oakland once again gave away a generational talent for little in return. Moss had worn out his welcome in Oakland only two seasons after doing the same in Minnesota.
His stock had plummeted as a result, and the always savvy Patriots were able to scoop him up for the low price of a fourth-round pick. Again, the rest is history as Moss was able to find a new lease on his career in New England. Many formerly troubled stars have seemed to do the same once they were under the tutelage of Bill Belichick. But few did what Moss did once he found a rhythm with Tom Brady. In 2007, Moss set the record for most touchdowns in a single season with 23 scoring receptions. The record still stands to this day and Moss is a Hall of Famer. Not bad for giving up a fourth-round pick to Oakland.
7. New England Trades Down, Misses Out On Jerry Rice:
This one isn’t often discussed when the worst NFL trades of all-time are brought up. The fact remains that it should be. Again, the Patriots are mainly known for being the club that gets the upper hand in trades these days, but this was long before the Bill Belichick era. Way back in 1985, the Pats received three draft picks from San Fran that allowed the 49ers to move up to No. 16 in the draft.
While it seemed like a good deal at the time, looking back, it most certainly was not. Rice came out of lesser-known Mississippi Valley State to take the NFL by storm. He won three Super Bowls as an integral piece of one of the NFL’s most storied dynasties. However, it’s his individual statistics that stand the test of time. Rice owns the NFL records for most receptions with 1,549, most receiving yards with 22,985, and most receiving touchdowns with 197. Those are numbers that may never be broken. It could be argued that Rice is the greatest player in NFL history. That makes this trade a horrible one for the Patriots.
6. Baltimore Colts Trade John Elway To Denver Broncos:
This mess of a situation ended up being arguably the most defining moment in Broncos history looking back. Former Stanford star Elway was adamant that he wouldn’t play for the Baltimore Colts if they drafted him with the first overall pick in the 1983 draft, but they did anyway. True to form, he refused to play. So they traded him to Denver for two players and a first-round pick.
All Elway did was become a two-time Super Bowl champ, a Super Bowl MVP, and a nine-time Pro Bowler. He made three total All-Pro teams and won an NFL MVP award. All told, he threw for 51,475 yards and 300 touchdowns. Elway is justifiably one of the greatest quarterbacks in NFL history, making this one of the worst trades ever based on the compensation the Colts received in return. They knew he wouldn’t play for them, yet created this situation unnecessarily.
5. San Diego Chargers Trade Arizona Cardinals, Draft Ryan Leaf:
As bad as the Colts’ aforementioned trading of Elway way, it might pale in comparison to the Chargers dealing for Leaf, who is often called the biggest bust in NFL Draft history. San Diego sent two first-round picks, a second-round pick, and two players, Eric Metcalf and Patrick Sapp, for the right to select Leaf at No. 2 in the 1998 draft. He promptly became a massive disappointment when he was selected one pick after Peyton Manning.
Leaf’s story is actually a very sad-yet-inspiring one. He became entrenched in a brutal addiction to opioids. He was arrested on several drug-related charges and later jailed. Leaf has worked hard to combat that his demons and now works with others to fight addiction. But in pure football terms, this was simply a botched trade from the outset. It badly hindered the Chargers franchise, which made a Super Bowl in the 1990s. They haven’t been back since.
4. Tampa Bay Buccaneers Trade Steve Young To San Francisco 49ers:
At the time they did, you couldn’t really blame the Tampa Bay Buccaneers for trading Young. After all, the team was a mere 3-16 with him at the helm, and he threw for only 11 touchdowns with 21 interceptions in his two years in Tampa. So they shipped him off to the San Francisco 49ers for second- and fourth-round picks. All Young did there was win three Super Bowls (one as a starter), a Super Bowl MVP award, and make seven Pro Bowls.
He was a two-time NFL MVP. To put his effectiveness in context, he led the NFL in passing touchdowns four times, in completion percentage five times, and in passer rating six times. Young finished his career with 33,124 yards, 232 touchdowns, and 107 interceptions. He had a 96.8 passer rating and also rushed for 4,239 yards with 43 touchdowns. The Bucs, meanwhile, were one of the worst teams of the 1980s and 1990s, yet that could have been much different had they only allowed Young to come into his own there. Perhaps he wouldn’t have without his time spent with Bill Walsh and Joe Montana in San Francisco, however. Overall, a horrible trade that dug Tampa Bay deeper into misery.
3. Atlanta Falcons Trade Brett Favre To Green Bay Packers:
This is another one similar to the stories of Steve Young and John Elway. For some reason, Atlanta decided to trade another quarterback who became one of the all-time greats when they sent Favre to the Green Bay Packers for a first-round pick. The story went that then-Atlanta head coach Jerry Glanville was concerned about Favre’s hard-partying ways as a young player.
Of course, he went on to become a Super Bowl champion who made 11 Pro Bowls and six All-Pro teams. Favre threw for 71,838 yards and 508 touchdowns in his Hall of Fame career. While he certainly inspired his fair share of controversy off the field due to his addictions and lewd photo scandal, Favre was an all-time legend. The Falcons traded away one of the greats here, and they haven’t won a Super Bowl since despite making two appearances.
2. Pittsburgh Steelers Trade Antonio Brown To Oakland Raiders:
This is a trade that seems to be getting stranger and stranger by the day. After refusing to play in Week 17 of the 2018 NFL season, Brown forced his way out of Pittsburgh in a trade to Oakland. Because of the drama he inspired, Oakland only gave up third- and fifth-round picks to acquire Brown despite his talent. Of course, they did have to sign him to a brand-new contract extension that included $30 million guaranteed. From the moment it began, this relationship was doomed. Brown showed up and worked hard in offseason training, but the wheels came off in training camp. First, he was reportedly absent when he froze his feet in a cryotherapy mishap. Then he became involved in a strange grievance with the NFL because he wanted to wear an outlawed helmet that was banned because of its ancient safety standards.
All that paled in comparison to what was to come, however. Brown repeatedly refused to show up to team activities, so Oakland general manager Mike Mayock fined him for it. Brown posted a photo of the fine letter on social media. It led to a confrontation where Brown allegedly called Mayock a racial slur and threatened to punch him in the face. He then apologized to the team the next day, but the team fined him again. Brown asked for and received his release and immediately went to the New England Patriots. While he made a successful debut there, Brown is now facing sexual assault allegations from two women and could be suspended. The Raiders got nothing for this trade, as Brown didn’t play a single game for them. For a summer, it tore their team apart from the inside.
1. Dallas Cowboys Trade Herschel Walker To Minnesota Vikings:
What else could top this list than the bad trade to end all bad trades? In a move that will forever live on in NFL infamy, Dallas traded running back Herschel Walker and four draft picks to the Vikings for a haul of five players and an incredible eight picks. These picks set the foundation for the Cowboys’ Super Bowl dynasty of the ‘90s. They drafted all-time great running back Emmitt Smith with one of the picks in addition to Pro Bowl safety Darren Woodson.
Using those picks along with a ton of other talents, the Cowboys won three Super Bowls that decade. The Vikings did not. Walker never even topped 1,000 yards for Minnesota – his highest single-season total was only 850. He only played for the team for two seasons, hardly worth a trade the Vikings mortgaged their entire immediate future for. Because it set the Cowboys dynasty in motion and the Vikings back for so long, this is the worst trade in NFL history.