22. Carolina Panthers Trade Kelvin Benjamin To Buffalo Bills:
A towering wideout from Florida State, Benjamin had the look of a true rising star in his first NFL season back in 2014. A torn ACL cost him his 2015 season, and he returned in 2016 not quite looking the same.
But that didn’t stop the Buffalo Bills from convincing themselves he was worth the high price tag of a third- and seventh-round selection. They sent just that to Carolina at the 2017 NFL trade deadline. It’s safe to say he wasn’t quite worth it. Benjamin showed little effort in Buffalo, even reportedly turning down new quarterback Josh Allen’s offer to catch passes before a game. The Bills eventually released him. They received essentially nothing for the two draft picks they traded away. As for Benjamin, he’s now out of the NFL.
21. Detroit Lions Trade Roy Williams To Dallas Cowboys:
Prior to the 2008 season, the Detroit Lions traded Roy Williams and a seventh-round draft pick to the Dallas Cowboys for first, third, and sixth-round picks. It’s safe to say this was not a good deal whatsoever. Williams promptly turned in three lackluster years with the Cowboys.
His best year was one where he secured only 38 catches, in fact. Now, we all know that Detroit hasn’t exactly done a ton with their draft capital in recent years either. However, in this instance, they certainly fleeced the Cowboys for a haul of picks that ultimately resulted in the Cowboys having a problem on their hands rather than a star wideout. Based on Williams’ production, this trade was an all-out bust.
20. New England Patriots Trade Jimmy Garoppolo To San Francisco 49ers:
It’s no doubt true that the New England Patriots are known for fleecing other teams by acquiring great talent and/or draft picks in deals that almost always work out for them. However, this was a (very) rare instance where the Patriots were somehow the team being fleeced. They sent potential star quarterback Jimmy Garoppolo to the San Francisco 49ers for the low price of a second-round pick in 2017. The ‘Niners promptly extended Garoppolo’s contract after he set the league on fire with five straight wins to close out that season. This made the Patriots look unbelievably bad. There’s a backstory to the deal as well.
Reports surfaced that there was turmoil in the Patriots’ camp because head coach Bill Belichick wanted to keep Garoppolo for the future while legendary quarterback Tom Brady didn’t want him breathing down his neck. The Patriots weren’t going to pay Garoppolo so they had to trade him. But this deal just looks terrible on paper. Garoppolo isn’t a huge star yet, but he definitely has San Francisco on the rise.
19. Chicago Bears Trade San Francisco 49ers, Draft Mitchell Trubisky:
This trade could end up being much, much higher on the list if the current trends play out over the course of many years. In 2017, the Chicago Bears traded two second-round picks and a fourth-round pick to San Francisco so they could select former North Carolina quarterback Trubisky with the No. 2 overall pick. They did all this despite much pre-draft chatter that Trubisky, despite possessing solid combine numbers, had only started one year in college.
But the real reason that makes this trade an all-out bust thus far is the fact the Bears could have had NFL superstar Patrick Mahomes instead. Mahomes was drafted at No. 10 that year when the Kansas City Chiefs traded up to select him. Making matters worse, the Bears also could have drafted former Clemson star Deshaun Watson as well, who was selected two picks later by the Houston Texans. He’s also well on his way to becoming one of the NFL’s best quarterbacks. Trubisky, however, is not, making this an outright atrocious trade. This trade could haunt Chicago for many years to come and already is.
18. Pittsburgh Steelers Trade Martavis Bryant To Oakland Raiders:
The Oakland Raiders just haven’t been a very good franchise in recent years, and trades like this are a big reason why. When former Oakland coach Jon Gruden returned with a ludicrous 10-year, $100 million contract before the 2018 season, he made some incredibly stupid moves as the team’s de facto general manager. One of the worst (although more will appear on this list) was trading a third-round pick for troubled Pittsburgh Steelers wideout Martavis Bryant.
They did so despite the fact that Bryant had repeatedly been suspended for off-the-field issues with drugs. He was even banned for the entire 2016 season. Then, he became discontented with Pittsburgh in 2017 and asked to be traded. They finally did after the season. But Bryant didn’t deliver for the Raiders. No, he was actually released and is no longer in the NFL. The Raiders gave up a high draft pick for nothing.
17. Oakland Raiders Trade Amari Cooper To Dallas Cowboys:
The next in the long line of bad moves by the Raiders on this list. Cooper put up some solid seasons in Oakland, but never quite lived up to his fourth overall draft status in the Bay Area. Many whispered that was perhaps due to Oakland’s ineptitude at using him. But in any case, the team traded him to the Dallas Cowboys for a first-round pick at the 2018 trade deadline.
They turned that pick into safety Jonathan Abram. He looked to be a solid contributor on defense for the Raiders until he injured his shoulder and was placed on injured reserve. However, Cooper has become one of the most dangerous deep threats in the NFL in his time with Dallas. His numbers showed that in the second half of last season, and now he’s the premier passing game weapon on the blazing-hot Cowboys offense. After the Raiders’ even more boneheaded (and ill-fated) trade for Antonio Brown earlier this year, they’re probably wishing they had Cooper back on the team.
16. Miami Dolphins Trade Wes Welker To New England Patriots:
Welker was decent enough as a receiver and kick returner in Miami. But they obviously didn’t think his contract was worth extending when they traded him to division rival New England for some reason. The Dolphins got second and seventh-round picks for Welker in 2007.
The rest, as they say, is history, as Welker became one of the most effective wide receivers in the storied history of the NFL juggernaut Patriots. He racked up receptions seemingly at will, catching well over 100 balls in multiple seasons. Miami could never get the same production out of him, but leave it to Bill Belichick’s system (and playing with Tom Brady) to get the most out of a player.
15. Washington Redskins Trade St. Louis, Draft Robert Griffin III:
This blockbuster trade is a tale of two sides. The Redskins paid a veritable king’s ransom to move up to No. 2 in the 2012 NFL draft and select Griffin III. They shipped three first-round picks and a second-rounder to the Rams, and for a while, it looked like it was a great move. Griffin III took the NFL by storm for a very brief while that season. Talk was that his read-option style was the next evolution of professional football.
But that hype train crashed almost as quickly as it arose. Griffin III injured his knee towards the end of his impressive rookie year, yet Washington coach Mike Shanahan sent him out to play in the playoffs regardless. There, the young quarterback tore his ACL and was never the same. Reports of a strange in-house situation the following season eventually arose as well. Yet ultimately Griffin III was a shell of his former self after that injury. He bounced around the league and sustained several more ailments. He’s now a backup for Baltimore. This one had potential but ended up being one of the worst trades ever when all was said and done.
14. Cleveland Browns Trade Trent Richardson To Indianapolis Colts:
Like Robert Griffin III, Richardson showed much promise as a rookie in 2012, rushing for almost 1,000 yards and 11 touchdowns as a member of the Browns. But that would be by far the peak of his success. Richardson played just two games for Cleveland the following season before they shipped him to the Indianapolis Colts for the steep price of a first-round draft pick.
The Colts may have believed the former third overall pick would finally live up to his lofty draft billing as a member of their offense. They were wrong. Richardson averaged a paltry 2.9 yards per carry for the Colts in 2013. He was only somewhat better in 2014, averaging 3.3 yards per carry. When he missed the Colts’ AFC title game in early 2015 due to an unreported emergency, the team decided to release him that March. He bounced around to the Oakland Raiders and Baltimore Ravens but never played another official NFL down. Richardson is largely considered one of the biggest NFL draft busts in history as a result. In this context, the Colts got one of the worst returns they could have imagined for a first-round pick.
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.