NFL: Top 5 Lopsided Trades of all time

Kansas City Chiefs vs Denver Broncos
Kansas City Chiefs vs Denver Broncos

There's an old saying in the NFL that a season can be won and lost long before the actual team takes the turf.

They say this because of the importance of the NFL offseason when franchises need to get their houses in order: the right players need to be resigned; the wrong players have to be let go; the correct players need to be drafted in, and the trades made need to heavily favor your organization. Failure to do these things can lead to a prolonged absence from the playoffs.

We have all sat there and restructured our favored team in Madden, and it seems so easy, right? Just switch Drew Brees to back up for the year in case he decides not to retire; turn off the salary cap; switch Deshaun Watson to kicker; sign him up in return for a couple of duds, and off you go. Simple, right?

Wrong! Unfortunately, making a trade like this in the NFL is impossible. Several franchise teams have been known to massively overreach in the draft and trades and there have been several lopsided trades over the years as a result of this; trades that have cost teams success not just in the short term but in the long run.

Considering moving for De'Von Achane? Fire up our Trade Analyzer to get a fair deal

With that in mind, let's take a look at the:

5 most lopsided trades in NFL history:

In descending order:

#5 NFL Trades: Mike Ditka bets the house on Ricky Williams

Miami Dolphins 2009 Headshots
Miami Dolphins 2009 Headshots

There isn't a lot of negative stuff you can say about Chicago Bears legend Mike Ditka. However, his short stint as boss of the New Orleans Saints in the late-90s has gone down as one of those things you could say: things did not go well.

Ditka bet the house on Heisman-winning running back Ricky Williams in the 1999 NFL Draft, trading all eight of New Orleans' picks to the Washington Redskins to land his man.

Things did not work out one bit: the Saints went 3-13 that year, and coach Ditka was unceremoniously fired for his accidental espionage.

Ricky Williams did enjoy some success down in the Bayou and registered over 3,000-yards rushing before moving on to Miami, where he is most fondly remembered. But Ditka's decision to sacrifice eight picks on a running back has to go down as one of the most bizarre moves in NFL history and is commonly cited as the main reason for the Saints' woes in the early 00s.

Eight picks on a running back is about as lopsided as it gets!

#4 NFL Trades: New York Jets trade Jamal Adams to the Seattle Seahawks.

Seattle Seahawks v Washington Football Team
Seattle Seahawks v Washington Football Team

The New York Jets allowed pro-Bowler Jamal Adams to move cross-coast to the Seattle Seahawks in one of the biggest NFL trades last year. The Seahawks received probably the best safety in the NFL and a third-round (2021 pick). In return, Seattle had to cough up two first-round draft picks (2021 and 2022), a third-round draft pick (2021), and safety, Bradley McDougald. That's a LOT of picks for safety.

We won't really know who came out on top of this deal until after the Jets have spent their picks in the 2021 NFL Draft. But for my money, two first-round picks on a safety (talented as he might be) could prove detrimental to the Seahawks' rebuild, and could potentially be another reason behind recent reports of Russell Wilson's dissatisfaction with the franchise -- Seattle is not exactly in a position to go out and get the young talent it needs to succeed, and Wilson will be only too aware of this.

Pete Carroll needs to execute his 2021 NFL Draft perfectly if the Seahawks aren't to come out of this one with a loss, and that's why it makes the list (for now...).

#3 NFL Trades: Patriots allow 49ers to snap up Jerry Rice.

San Francisco 49ers vs Green Bay Packers
San Francisco 49ers vs Green Bay Packers

As incredible as this might sound given what the man went on to achieve in his storied career in the NFL, Jerry Rice was not exactly considered hot-property in the 1985 NFL Draft: the legendary receiver had underperformed in the 40-yard dash (more evidence that you cannot pluck for players based on their NFL-combine-performance alone).

Bill Walsh of the 49ers, one of the few coaches who remained optimistic regarding Rice's potential, opted to trade the 49ers' first two picks in the 1985 draft to the Patriots, a move which saw the 49ers climb up the board from 28th to 16th. The move put Walsh in a position to snap up Jerry Rice, arguably the greatest player in any position to have ever played the game of football.

The Patriots used San Francisco's picks to bring Trevor Matich and Ben Thomas to New England (I forgot about them too, don't worry).

Trading Matich and Thomas for the greatest wideout ever seen in pro-football has to go down as one of the most lopsided trades of all time; hence it makes the list at number three.

#2 NFL Trades: John Elway's outright refusal to play for the Baltimore Colts

San Diego Chargers vs Denver Broncos
San Diego Chargers vs Denver Broncos

John Elway entered the 1983 NFL Draft as the consensus pick for the best quarterback in the class in what was to be one of the greatest QB classes of all time: John Elway, Todd Blackledge, Jim Kelly, Tony Eason, Ken O'Brien, and Dan Marino, all went in the first round!

Upon hearing that he was to be drafted by the lowly Baltimore Colts with their number-one pick in the draft, Elway made it clear that he was prepared to sacrifice his career in the NFL in favor of a baseball career.

Former Colts owner Robert Irsay decided to go ahead and draft Elway anyway, but this turned out to be an erroneous decision; Elway wasn't messing around; he had no intention of ever playing for the Baltimore Colts, and the threat to switch sport continued.

Irsay did eventually give in to Elway, sending him to the Broncos in return for a first-round pick, quarterback Mark Herrmann, and offensive lineman Chris Hinton.

Elway is regarded as one of the best QBs to ever play the game of football. He won two Super Bowls with Denver and was selected to the Pro-Football Hall of Fame in only his first year of eligibility.

Any time you lose out on an NFL quarterback like Elway, it has to be considered a lopsided trade. Irsa and the Baltimore Colts never really recovered from the blow of losing Elway and moved to Indianapolis three years later.

#1 NFL Trades: The Vikings pay way over the odds for Herschel Walker

Dallas Cowboys vs New York Giants
Dallas Cowboys vs New York Giants

If you read my other two recent articles: top 5 blockbuster trades and top 5 worst trades (click for link), you're possibly sick to death of reading about Herschel Walker (Vikings fans, I'm sorry). But alongside being the most blockbuster trade (Emmit Smith and Charles Woodson!), and the worst trade (Vikings lost so many picks for a running back that didn't get it done), the Herschel Walker trade also has to be the most lopsided. The trade has to be number one on all three lists. It just has to be!

Here's why:

When the Cowboys decided to trade Walker to the Vikings, plus their third-and a 10th-round pick in the 1990 NFL draft; the San Diego Chargers' fifth-round pick (which the Cowboys received in a trade for running back Darrin Nelson) and their third-round pick in the 1991 NFL Draft... in exchange for Minnesota' linebackers Jesse Solomon and David Howard, defensive end Alex Stewart, cornerback Issaic Holt and first-,second-and sixth-round picks in 1990, alongside a second-round pick in the 1992 NFL Draft back to Dallas... when the Cowboys did all that, given Walker didn't have much success in Minnesota, you could say the Cowboys were up on the deal.

That wasn't all, though: the Dallas war room had been very tactical in the way they structured the trades for the likes of Howard, Stewart, and Solomon. Somewhere in the fine print was a killer blow for the Vikings: if any of these players were released by Dallas coach Jimmy Johnson, the Cowboys would be entitled to more of Minnesota's draft picks, and the Cowboys organization was originally prepared to exercise their contractual obligations with ferocity. Case in point, Johnson waived goodbye to Stewart in November 1989 which meant the Vikings had to surrender yet another NFL draft pick.

It could have been even worse for the Vikings, but the Cowboys evidently took pity on the ghastly deal they were giving their Minnesotan counterparts. Johnson decided not to cut the other three players he'd signed from the Vikings, striking a deal to keep them on the books, thus sparing any more purple blushes.

Herschel Walker didn't find much success in Minnesota with the Vikings, but he wasn't a terrible player either. The former Cowboy appeared just once in the playoffs before signing with the Philadelphia Eagles in time for the 1992 NFL season.

Dallas used the picks given to them by the Vikings to bring in such talents as running back Emmitt Smith, defensive tackle, Russell Maryland, and safety, Darren Woodson. These players formed the backbone of the Cowboys team that went on to dominate the NFL in the early 1990s, winning three Super Bowls.

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Edited by Ashwin
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