Five of the Worst NFL Trades Ever

By Blake Roberts Founder & Editor in Chief Updated: 09 August 2023

Blake Roberts Founder & Editor in Chief

Blake Roberts is the founder of Betting.US and is currently heading the creative team as Editor in Chief. Born and raised in Morgantown, West Virginia, Blake is a great sports fan, with football and basketball being his favorite. He’s our trusted voice for all betting-related matters.

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The Worst NFL Trades

• Worst Trades in NFL History
• What Makes the Worst NFL Trades of All Time?
• The Herschel Walker Disaster
• Ricky Williams: A Bet Too Far
• Brett Favre to Green Bay
• Randy White to Dallas
• The John Elway Trade
• Frequently Asked Questions

In the high-stakes game of professional football, franchises gamble on players, hoping for rewarding returns. Unfortunately, not every gamble pays off, leading to some shocking and frequently debated trades.

Over the history of the NFL, there have been some amazing trades made – but there have also been some absolutely dreadful ones, and that’s what we’re going to be covering in today’s blog. We’ll show you the worst NFL trades ever, why they were bad, why they happened in the first place, and the legacy they left on the team and players involved.

Worst Trades in NFL History

In this blog, we’re exploring the worst trades in NFL history. From over-valued player transfers to highly imbalanced trades, these deals have had a lasting impact on the teams involved, and some teams struggle to shake the consequences from these trades seasons later. Today, we’ll dive deep into each trade, discussing what went wrong, the impact on the teams, and the fallout in the years that followed.

What Makes the Worst NFL Trades of All Time?

The makeup of a bad NFL trade is multifaceted and, sometimes, subjective. At the core, a trade is considered to be a poor one when it results in a noticeable imbalance in the value received by the teams involved. There are several factors that can lead to the worst NFL trades of all time being made, some of which we’ll look at below.

One of the biggest factors is when a team overestimates a player’s potential or value. This can be due to a team’s internal biases, flawed player evaluation methods, or simply an ill-considered gamble on a player’s future performance. When a team trades away significant resources or players for a player who doesn’t live up to the expectations, it can severely damage the team’s performance and potential, sometimes for years to come.

Another common factor behind the worst trades in NFL history is when a team undervalues draft picks. Draft picks are crucial for a team’s long-term success as they provide the opportunity to acquire young and talented players on team-friendly contracts. However, teams often undervalue these picks in the hopes of more near-sighted success, often backfiring when the traded player then fails to make the impact they’d expected.

Another reason is a lack of foresight or understanding of a team’s own needs. This can lead to awful trades; for example, a team might trade away a key player in a position where they lack depth, only to find themselves desperately needing that exact player’s talent down the line.

If you’re a fan of NFL mobile betting, you’ll already know the thrills that come with watching games live, especially after a major trade has been made. If you’re looking for the best bookmakers for NFL betting, make sure to check out our recommended sites, all of which are hand-picked by our team of online betting experts.

The Herschel Walker Disaster

In 1989, the Dallas Cowboys and Minnesota Vikings orchestrated what would become known as one of the worst NFL trades of all time – the Herschel Walker trade. The Cowboys sent Walker, their Pro Bowl running back, to the Vikings in a deal that involved a record-breaking 18 players and draft picks.

The Vikings were hoping that Walker, a dynamic and productive player, would be the missing piece to their Super Bowl puzzle. However, the gamble didn’t pay off as Walker’s performance in Minnesota was a far cry from his top-level performance in Dallas. He played just two and a half seasons for the Vikings, never rushing for more than 1,000 yards in a season.

On the other side, the Cowboys used the large number of draft picks they received to construct a fantastic team. They drafted players like Emmitt Smith, Darren Woodson, and Russell Maryland, who were instrumental in their three Super Bowl wins in the 1990s. It’s widely considered to be the worst trade ever and has gone down in history as a warning to other franchises not to overvalue players, even if they’re superstars.

Ricky Williams: A Bet Too Far

In the 1999 NFL Draft, New Orleans Saints coach Mike Ditka and general manager Bill Kuharich arranged what would become one of the most controversial trades in NFL history. The Saints traded away their entire 1999 draft and a first and third-round pick in the 2000 draft to the Washington Redskins to move up and select Ricky Williams, the Heisman Trophy-winning running back from Texas.

The Saints had high hopes for Williams, but this gamble didn’t pay off. Williams struggled with injuries and inconsistency during his three seasons in New Orleans, while the Saints remained a pretty mediocre team. They eventually traded him to the Miami Dolphins for four draft picks, which included two first rounders.

While it wasn’t as bad for the Redskins, they also didn’t see much benefit from the trade. They did, however, gain increased flexibility to improve their team, and for both teams, the trade showed the risk of betting too much on a single player.

Brett Favre to Green Bay

The trade of Brett Favre from the Atlanta Falcons to the Green Bay Packers in 1992 is a classic case of undervaluing a player’s potential. Favre, then a second-year quarterback, was traded to Green Bay for a single first-round draft pick after spending his rookie year in Atlanta as a backup.

The trade is viewed as one of the worst in NFL history due to Favre’s subsequent success with the Packers. Under coach Mike Holmgren, Favre quickly became a star, rising to become one of the most exciting and successful quarterbacks in the league. He led the Packers to a Super Bowl victory in 1996, earned three consecutive MVP awards, and set several NFL records during his time in Green Bay.

On the other hand, the Falcons didn’t get the same level of return from the draft pick they received. The player they drafted, running back Tony Smith, had a pretty underwhelming NFL career, and this trade deal underscores the importance of getting a realistic idea of a player’s potential.

Randy White to Dallas

The Dallas Cowboys made one of the most notable trade steals in the 1975 NFL Draft when they acquired the second overall pick from the New York Giants. They used the pick to draft Randy White, a defensive tackle from Maryland.

The Giants received two Cowboys veterans, quarterback Craig Morton, and a 1976 first-round pick in return. Morton had a couple of good seasons with the Giants but was nowhere near as impactful as White was for the Cowboys.

Randy White, on the other hand, became a cornerstone of the Cowboys’ defense. He played his entire 14-year career with the Cowboys, earning 9 First-Team All-Pro selections, a Super Bowl victory, and a Super Bowl MVP. It was one of the best decisions the Cowboys ever made, and many say they wouldn’t have won their Super Bowl title if White wasn’t on the team.

The John Elway Trade

In 1983, the Baltimore Colts drafted John Elway with the first overall pick. However, Elway had no intention of playing for the Colts and forced a trade to the Denver Broncos. This trade would go down in history as one of the worst – and most humiliating – as Elway led the Broncos to two Super Bowl victories.

This was definitely one of the worst NFL trades ever, but there are a number of other trades that are equally as bad. Check them out below: