5 unexpected NFL trades that made no sense

NFL Trades: Extreme Overpays

#3 - Chicago Bears move up in the NFL Draft to select QB Mitchell Trubisky

Regretful NFL trades come in a variety of forms. The Chicago Bears' move up in the NFL Draft to select Mitchell Trubisky looked like a bad decision at the time but got even worse as it played out. The Bears surrendered a first, two-thirds, and a fourth-round draft pick to move up just one spot in the NFL Draft to select a quarterback that could have been taken much later.

To make things even worse, the Bears passed on two other quarterbacks who elevated themselves to superstar status while Trubisky was overall a bust. The two were Patrick Mahomes and Deshaun Watson. This is one of the most frustrating NFL trades ever, especially for the Bears faithful.

#2 - New Orleans Saints trade away their future for RB Ricky Williams

Ricky Williams is an elite college running back for the Texas Longhorns and a highly rated prospect. It was also an era in the NFL where running backs were valued much higher than they are today. The desire for Ricky Williams made sense but the Saints gave up way too much to get him.

NFL trades involving draft picks happen all the time, but rarely to the extent of this deal. The Saints surrendered eight total draft picks, including their entire set of picks in the 1999 Draft and two top picks the following year. Williams went on to be a solid back, but few players in NFL history could justify that price tag.

#1 - Dallas Cowboys trade Herschel Walker for a dynasty

Herschel Walker went down as one of the most infamous NFL trades of all time. It is credited as a move that sparked the Dallas Cowboys dynasty of 1990s when they won three Super Bowl rings. It's one of the most monumental NFL trades in history.

Jerry Jones made his mark on the Dallas Cowboys when he sent Herschel Walker to the Minnesota Vikings in a controversial and massive move. Walker was packaged with four draft picks to return five players and eight draft picks, including three first-rounders and three second-rounders. It helped the Cowboys build one of the best overall teams in NFL history.