Trading has been a big part of NFL history, with some transactions setting the landscape of the league for years to come. Whether it’s during the offseason or during the NFL Draft, trades have shaped NFL history. 

There have been plenty of bold moves made by general managers and players both. Let’s go through some of the best and worst trades in NFL history, and how it impacted the league. Don’t forget to also check out the NFL pool contests to compete against friends and family!

NFL Draft Day Trades and Trade Deadline

Many NFL trades take place during the NFL Draft, a weekend long event that involves various franchises selecting collegiate players to their team. During drafts, picks are often swapped but on occasion players are also traded. 

Some of the most famous trades have occurred during the NFL Draft. The Chargers drafted then traded away Eli Manning to acquire the New York Giants’ pick, Philip Rivers. Another Chargers’ trade saw them give the No. 1 pick to the Atlanta Falcons, as the latter took Michael Vick and the Chargers took LaDainian Tomlinson and Drew Brees. 

Teams also wait until the trade deadline to make trades, rare but possible. In a recent blockbuster trade deadline move, the San Francisco 49ers acquired Carolina Panthers’ running back Christian McCaffrey. The Miami Dolphins also went out and got Denver Broncos’ defensive end Bradley Chubb. 

The Biggest Trades in the NFL 

Trades can go in various directions, as teams can win or lose a trade. In some cases, both teams win or lose on a trade. Below are the biggest NFL trades in history. 

The Herschel Walker Trade

This is considered to be the biggest trade in the history of the NFL, as it involved 18 players and multiple draft picks. Walker was sent from the Dallas Cowboys to the Minnesota Vikings that also involved a transaction from the San Diego Chargers. 

Following the trade, Dallas used the draft picks it acquired from Minnesota to get players that eventually won three Super Bowls. Minnesota didn’t make a Super Bowl appearance with Walker on the roster. 

Eric Dickerson to the Colts

A 10-player trade saw the electric Eric Dickerson leave the Los Angeles Rams and join the Indianapolis Colts. The trade occurred on Halloween in 1987 if that wasn’t spooky enough, but his performance when he got to Indy was anything but spooky. 

Dickerson ran for over 1,000 yards in his final nine games with the Colts, leading them to a 9-6 record and their first playoff appearance since 1977. The trade was only beneficial short term however, as Dickerson wanted out by 1991 when the Colts went 1-15. 

Deshaun Watson to the Browns

In perhaps the most controversial trade in NFL history, the Houston Texans sent quarterback Deshaun Watson to the Cleveland Browns following an insane amount of sexual misconduct incidents. Besides Cleveland trading for Watson, the other controversy sparks from the amount of guaranteed money the Browns offered him following over 60 accusations. 

Watson served a suspension for his first year in Cleveland and didn’t play much better when he returned. Watson is set to make over $200 million with the Browns as their signal caller. 

Russell Wilson to the Broncos

The Super Bowl winning Seattle quarterback was sent to Denver after requesting to leave town, claiming the offensive line didn’t protect him. Denver sent over two first round picks, two second round picks and fifth round picks and three players for Wilson.

The following year Denver ranked last in points per game, and Wilson didn’t finish the season as head coach Nathaniel Hackett was eventually fired. There’s still time for Wilson and the Broncos to prove this trade was worth the investment, but after one season the Broncos looked to come up extremely short in the trade with Seattle. 

Khalil Mack to the Bears

Jon Gruden took over the Raiders and immediately made changes, none were more notorious then sending his best player to the Chicago Bears. The Raiders got back multiple first and second round picks, while the Bears ended up signing Mack to a 6-year, $141 million dollar contract. 

Ricky Williams to the Saints

Prior to the 1999 NFL Draft, running back Ricky Williams was a hot commodity. He was so popular that Eagles fans booed Donovan McNabb because they wanted to draft Williams instead. The Saints moved from the 12th pick to the 5th pick to take Williams, giving up all their 1999 draft picks and two of their first three picks in 2000. 

John Elway to the Broncos

Much like Eli Manning did when he said ‘thanks but no thanks’ to being taken No. 1 overall, John Elway told the Baltimore Colts the same. The Colts had the first pick in the NFL Draft and took John Elway, who told the franchise he wasn’t going to play for them (Eli did the same to the Chargers). Six days after the draft, Denver acquired Elway for two players and the 1984 first round pick, which ended up being Ron Solt. 

Brett Favre to the Packers

The Atlanta Falcons would love to have this trade back, after sending the what would be Hall of Fame quarterback to Lambeau. After just one season with Atlanta, the Falcons sent Favre to Green Bay in 1992.

Just three games into the 1992 season Favre started at quarterback for Green Bay. He went on to win 160 regular season games, three NFL MVP awards and brought the Lombardi trophy back to Green Bay since Lombardi himself won it. 

Steve Young to the 49ers

The 49ers may have had the biggest trade victory in NFL history in 1987, getting rid of a second and fourth round pick for Steve Young. The Tampa Bay Buccaneers acquired Vinny Testaverde in the draft, so they wanted to rid Young as the Niners were looking to replace an aging Joe Montana. 

Young went on to claim a 91-33 record, a Super Bowl trophy, two MVP awards and three All-Pro selections. He was also inducted into the Hall of Fame in 2005, so it’s safe to say San Francisco won that trade. 


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