• While notoriously the worst trade in NFL history, for one team, the Herschel Walker move was golden.

  • In 2004, the Chargers and Giants swapped rookies who would become their franchise quarterbacks.

  • Arguably the best wide receiver of all time landed at his first team thanks to a draft day trade.


The bulk of the team building in the NFL is done in the free agency and on draft day, but now and then, two teams strike a deal that completely alters the trajectory of at least one of them. 

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Looking at trades on draft day, during the season, and those that sent the picks that became star players, these are the best trades in NFL history ranked. 

1 – Eight Draft Picks for Herschel Walker (1989)

While the Minnesota Vikings get the title of the team that was on the losing end of the worst trade in NFL history, for the Dallas Cowboys, their return would set them as the receiving party of the best trade in NFL history. 

Herschel Walker had enjoyed a very good 1988 season, and despite starting slow in 1989, the Vikings were desperate enough to add what they thought was the final piece to a Super Bowl-winning puzzle.

On 12 October 1989, the Cowboys received running back Darrin Nelson, linebackers Jesse Solomon and David Howard, cornerback Issiac Holt, and defensive end Alex Stewart, along with eight picks.

To get all eight of the picks – only three of which were guaranteed – the Cowboys had to cut the four players they received and trade Nelson to the Chargers, which the Vikings didn’t expect them to do.

In the end, the Cowboys received Minnesota’s first-round picks in 1990, 1991, and 1992, second-rounders in those three years, and an extra third in 1992 and sixth in 1990. 

Vikings didn’t just get Walker, though. They also received Dallas’ third-rounders in 1990 and 1991, the fifth-rounder traded from San Diego for Nelson, and the Cowboys’ tenth-round pick in 1990.

That haul of picks helped the Cowboys to build a dynastic team that dominated throughout the 1990s, bringing in the likes of Emmitt Smith, Russell Maryland, and Kevin Smith either directly or as a piece of a trade to get to them.

By 1995, Dallas had added three more Lombardi Trophies to the cabinet. By 1992, Walker was in Philadelphia, and the hunt for Minnesota’s first Super Bowl goes on to this day.

2 – Philip Rivers for Eli Manning (2004)

It’s rare that an NFL trade ends up benefitting two teams as close to equally as you can get, but that’s exactly what happened with this second-ranked best trade in NFL history.

At the 2024 NFL Draft, Manning made it clear to the Chargers that he didn’t want to play in San Diego, but they drafted him first overall anyway. Later, the Giants picked up Philip Rivers fourth overall. 

The Chargers drafted the more highly-rated Manning, but Rivers would be their second choice. So, they swapped rookie QBs on draft day, with the Giants also sending a 2004 third-rounder and 2005 first and fifth-round picks.

With Manning, the Giants would go on to win the Super Bowl twice while their star QB collected a string of franchise records over his 15 years under centre. 

San Diego also enjoyed 15 years of Rivers, and he also boasts a haul of franchise records with eight call-ups to the Pro Bowl. Plus, two of the three added picks turned into Pro Bowlers – Shawne Merriman and Nate Kaeding.

Now, 20 years on, both the Chargers and Giants are desperately rebuilding, with the west coast team being ahead in the online betting odds mostly by virtue of their top-tier quarterback, Justin Herbert. 

3 – 49ers Trading Up for Jerry Rice (1985)

Not content with being the reigning Super Bowl champions and winners of two of the last four, San Francisco 49ers head coach Bill Walsh wanted to bolster his offence further with a deep-threat receiver. 

However, the 49ers knew that the Dallas Cowboys, picking 17th, were eyeing up their ideal selection, Jerry Rice. Way down at the end of the round as the champions, San Francisco had to bet fairly big to sneak in first. 

They sent the 16th-placed New England Patriots their first-round, second-round, and third-round picks to get the first and third-rounders of the Pats. 

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Leapfrogging Dallas, the 49ers drafted Rice to add who would end up being arguably the best wide receiver in NFL history – and certainly of his era. 

Rice boasts an absurd collection of records and accolades, including being the most prolific postseason receiver, winning three Super Bowls, getting 13 Pro Bowl call-ups, and he was a six-time receiving yards and receiving touchdown leader.

Thanks to another well-crafted trade that sent a few picks elsewhere, the 49ers are again major contenders in the NFL odds to win the Super Bowl.

4 – Brett Favre for a First-Round Pick (1992)

In 1991, the Atlanta Falcons snapped up Brett Favre in the second round with the 33rd overall pick. His rookie season, however, was blighted by a disapproving head coach who only let him attempt four passes. 

After this showing, the Packers came in with a first-round pick in 1993 to bring the young quarterback to greener pastures, even brushing aside the advice to fail his medical due to a hip condition that ended Bo Jackson’s career.

Over the next 16 seasons, Favre won two Super Bowls from three trips to the big game, put up a streak of 253 consecutive games, and remains the only player to win three AP MVP awards in a row. 

Later, the Packers drafted Aaron Rodgers and had him learn the ropes from Favre to become his heir-apparent, which gave Green Bay another 15 years of world-class shot-calling and another Super Bowl.

5 – Broncos Trade for John Elway (1983)

In another display of top-pick power, John Elway made it clear to the Baltimore Colts coming into the 1983 draft that he didn’t want to join the franchise and even threatened to pivot to baseball instead. 

The Colts were unable to deal their first overall selection before the draft, so they picked Elway, who was quoted as saying, “Right now, I’m playing baseball.”

Elway was selected on 26 April by Baltimore, and by 2 May, he was off to Denver to play for the Broncos.

Denver sent offensive lineman Chris Hinton, a 1984 first-rounder, and backup QB Mark Herrmann to get the young slinger.

Not only did Elway steer the team to two Super Bowl triumphs and collect himself nine Pro Bowl call-ups, but after retiring, he took on several senior positions in the organisation to help make the Broncos one of the most valuable sports teams in the world.


*Credit for the photos in this article belongs to Alamy*

Ben is very much a sports nerd, being obsessed with statistical deep dives and the numbers behind the results and performances.

Top of the agenda are hockey, football, and boxing, but there's always time for some NFL, cricket, Formula One, and a bit of mixed martial arts.