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Trades occur every year in the NFL, especially during the offseason and right before the trade deadline in the regular season. Teams execute trades for many different reasons, including adding finishing pieces for a postseason push or swapping veterans for future assets in a rebuild.
Every trade in the NFL carries a certain amount of risk, and of course, some are a much bigger gamble than others. Most of the time, the trade makes some sense for all of the teams involved in the deal, even if one team appears to have gotten a more impactful haul.
In rare cases, a trade goes down that just seems straight-out strange from the start. That said, here are five of the weirdest deals in NFL history that have left many around the league puzzled.
#5 - Chicago Bears trade up in the 2017 NFL Draft for Mitch Trubisky
The Chicago Bears gave away a package of five picks in the 2017 NFL Draft to move up one spot to make sure they got the quarterback of their choice. That quarterback ended up being Mitchell Trubisky. While he failed with the Bears, what makes it even worse is who they passed on to get him. Deshaun Watson and Patrick Mahomes were selected shortly after.
#4 - Jon Gruden traded to the Buccaneers for a haul
The Tampa Bay Buccaneers sent two first-round draft picks, two second-rounders, and $8 million in cash to the Oakland Raiders in exchange for head coach Jon Gruden ahead of the 2002 NFL season.
It seemed like way too much to give up for a coach at the time it happened, but it worked out for the Buccaneers in a big way. He defeated his former Raiders team in the Super Bowl, bringing the ring to Tampa.
#3 - Bill O'Brien swaps DeAndre Hopkins for David Johnson
While Bill O'Brien was a solid head coach for the Houston Texans, his skills as a general manager were often questionable. The best example of this was when he traded away a prime DeAndre Hopkins to the Arizona Cardinals for a seemingly washed-up David Johnson.
Hopkins was one of the best players in the league at the time, while Johnson was dealing with injuries and declining production. The move eventually got him fired shortly after.
#2 - Saints give away their future for Ricky Williams
Ricky Williams put together a legendary college football career with the Texas Longhorns ahead of the 1999 NFL Draft. The New Orleans Saints fell so in love with the prospect, they basically traded away their entire future to move up and select him.
They sent the Washington Redskins eight total draft picks, including two first-rounders and five picks in the first three rounds, for the right to select Williams. While he went on to become a solid running back, few players in NFL history can justify such a haul.
#1 - Buccaneers quickly give up on Steve Young
The Tampa Bay Buccaneers invested the number one overall pick in the 1984 supplemental draft to select Steve Young. He was a highly-rated quarterback prospect but struggled to live up to the hype with the Buccaneers.
He recorded a 3-17 record across three years before being traded to the San Francisco 49ers for a second and fourth-rounder. He eventually went on to win two NFL MVP awards and a Super Bowl ring on his way to the Hall of Fame. It was simply too soon for the Buccaneers to give up on a quarterback they used a number-one pick on.
