The worst NFL trade deadline deals in history: 5 Worst NFL trades in history

The NFL trade deadline is quickly approaching. Some teams could make trades that boost their playoff and Super Bowl odds, but others will make bad deals that hamper their rosters.

There's no way to know which trades will turn out the best until one is able to look back with the benefit of hindsight. However, several deals from the past have not aged so well in the years since they happened. More than a few bad moves happened midseason at the trade deadline.

The following five trades have aged exceptionally poorly and could be considered among the worst trade deadline deals in NFL history.

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Worst trade deadline deals in NFL history

5. Buffalo Bills acquire Kelvin Benjamin from Carolina Panthers (2017)

The 2014 first-round pick never quite lived up to the potential he showed in his rookie season with the Carolina Panthers. After catching 73 passes for 1,008 yards and nine touchdowns his first season, Benjamin missed the entire 2015 season after tearing his ACL in training camp.

After a 2016 that saw a moderate drop in the wideout's production, Benjamin played the first half of the 2017 season for Carolina on pace to put up similar numbers to what he did in 2016. After eight games, the Panthers traded him to the Buffalo Bills for 2018 third- and seventh-round picks.

The former Panther played just six games for the Bills that year after tearing his meniscus, and his production was hampered after he tweaked the knee injury following his return. Buffalo made the playoffs but lost its wild-card matchup with the Jaguars. Benjamin had just one catch for nine yards in the game.

Benjamin began the 2018 season playing on his fifth-year option for Buffalo since Carolina had exercised it the year before, but the receiver didn't even make it through his first full year with the Bills. The team cut him after just 12 games in which he caught 23 passes on 62 targets, a 35% catch percentage, a league-worst mark that year. He finished with 354 yards and one touchdown.

4. Chicago Bears trade for Chase Claypool (2022)

Chase Claypool enjoyed two seasons of solid production with the Pittsburgh Steelers after the team made him its second-round pick in 2020. Across 2020 and 2021, the Notre Dame product had 121 catches for 1,733 yards and 11 touchdowns.

In his third season, Claypool's role in the Steelers' offense diminished slightly after the team selected receiver George Pickens in the second round of the 2022 draft.

After Week 8 of the 2022 season, the Chicago Bears were 3-5 after a loss to the Dallas Cowboys on the road. Seeking a boost for its passing offense, Chicago traded its 2023 second-round pick for Claypool, matching the Packers' offer for the Steelers wideout.

The British Columbia, Canada native never played a full season for the Bears. In seven games in 2022, he caught just 14 passes for 140 yards. The next year, Claypool played in just three games, tallying four receptions for 51 yards and his only Bears touchdown before expressing frustration about how the team was using him to the media. He never played another snap for the Bears before they traded him to Miami in Week 5.

Chicago went on to lose every game after making the trade for Claypool in 2022, and the second-round pick it gave up was the first pick on the second day of the 2023 draft. Pittsburgh drafted cornerback Joey Porter Jr. with the selection, and he went on to finish fifth in the Defensive Rookie of the Year voting.

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3. Indianapolis Colts send first-round pick to Browns for Trent Richardson (2013)

Trent Richardson tallied 950 yards and 11 touchdowns on the ground, 367 receiving yards, and one touchdown catch as a rookie in 2012. At the time, he seemed the lone bright spot in an otherwise brutal year for the Cleveland Browns. First-round quarterback and 28-year-old rookie Brandon Weeden had the fourth-worst passer rating in the NFL. Cleveland finished 5-11 and in last place in the AFC North.

So, when the Browns traded Richardson just two games into the 2013 season, it was a bit of a shock to the NFL world. The shock faded once the Indianapolis Colts got their hands on Richardson in his second year in exchange for a first-round pick.

By Week 12 at the beginning of December, Indianapolis had already demoted Richardson to a backup role after nine games, averaging fewer than three yards per carry and just two touchdowns.

The Alabama product was only slightly better in his first full year with the Colts in 2013, and the team waived him the following offseason. He never played another regular-season snap in the NFL.

Thanks to a solid second year from Colts quarterback Andrew Luck, the pick Indianapolis sent to Cleveland ended up in the back third of the first round. That year, the Browns traded up from that 26th pick to take another swing at a franchise quarterback: Johnny Manziel.

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2. Green Bay Packers think John Hadl is their franchise quarterback (1974)

In 1973, a 33-year-old Hadl played in his first season with the Los Angeles Rams after 11 years with the San Diego Chargers. By the end of the year, the former Kansas Jayhawk earned a sixth Pro Bowl nod to go along with his first-team All-Pro honors (a career first) and second-place finish in MVP voting behind running back O.J. Simpson.

The following year, Hadl started the Rams' first five games before being benched in the fifth game in favor of James Harris, who became the first African-American quarterback to start an NFL playoff game later that year.

Seeing an opportunity to bring in a battle-tested veteran quarterback, the Green Bay Packers sent five draft picks (two first-round picks, two second-round picks, and a third-rounder) to Los Angeles in a midseason trade for Hadl in 1974. The deal only came about because a similar trade attempt for New Orleans Saints quarterback Archie Manning fell through.

Hadl was a disaster in Green Bay. During his one-and-a-half years with the Packers, he led the team to a 7-12 record while throwing just nine touchdowns to 29 interceptions.

Meanwhile, the Rams went on to win six straight NFC West division titles and made a Super Bowl appearance with the help of some of those draft picks. Both cornerbacks Monte Jackson and Pat Thomas, second-round picks for the Rams in 1975 and 1976, earned multiple Pro Bowl nods with Los Angeles.

1. Minnesota Vikings trade their future for Herschel Walker (1989)

The Minnesota Vikings' trade for Herschel Walker is among the worst trades in NFL history, midseason or otherwise. It even has its own Wikipedia page.

Walker had established himself as Dallas' best player by 1988, his third season as a pro.

The year before, the former Georgia Bulldog led the NFL with 1,606 yards from scrimmage on 269 touches and earned Pro Bowl and second-team All-Pro nods. In 1988, he rushed for 1,514 yards and five touchdowns and caught 53 passes for 505 receiving yards to put him at 2,019 scrimmage yards. It was enough for another Pro Bowl appearance, second-team All-Pro honors, fifth place in MVP voting, and a sixth-place finish for Offensive Player of the Year.

It was enough for a Vikings team fresh off of two straight playoff appearances to make a blockbuster deal for the running back five weeks into the next year. In October 1989, Minnesota received Walker and three future draft picks for five players, three draft picks, and additional picks conditional on the Cowboys cutting those five players.

Ultimately, Dallas didn't play any of the players it acquired in the trade. As a result, the Cowboys got the Vikings' first- and second-round picks in 1990, 1991, and 1992, as well as Minnesota's sixth-round pick in 1990 and third-round pick in 1992.

The Cowboys eventually used those picks to make several additional trades, landing five other players, including running back Emmitt Smith and safety Darren Woodson, to build a roster that dominated the 1990s. Dallas won three Super Bowls between 1992 and 1995.

Meanwhile, Walker played just two full seasons for the Vikings and never exceeded 850 rushing yards in a season. Minnesota missed the playoffs in all but that first year, 1989, with its new running back.

This article originally appeared on USA TODAY: NFL trade deadline: 5 worst midseason deals in NFL history