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.