NFL Trade Deadline: 30 greatest trades in NFL history

28. Bears give up first-round picks for Khalil Mack

After weeks of holding out during training camp and the preseason, the Oakland Raiders made the tough decision back in September to trade defensive end Khalil Mack to the Chicago Bears in exchange for a boatload of draft picks.

Two of those picks happened to be first-rounders. It’s safe to say if they were never included in the package, this deal may never have taken place between Oakland and Chicago.

In four years with the Raiders, Mack wasted little time making a name for himself as one of the league’s top defensive players. He even managed to record double-digit sacks each season from 2015 to 2017.

With this in mind, many questioned why a team like Oakland would give up on such an effective pass rusher.t Mack is the type of player any defense would love to have leading the way. But just like other situations around the NFL, the money factor came into play.

Prior to the start of the 2018 season, Mack had made it clear about his wish to be one of the league’s highest paid defensive players. Since the Raiders didn’t want to give in to his demands, a trade seemed like the best option for the Silver and Black.

Only time will tell when it comes to determining whether Oakland regrets this decision. At least they did gain two extra first-round picks out of the deal to give them an extra advantage heading into 2019 and 2020.

Let’s not forget, with the Raiders completing another deal involving wide receiver Amari Cooper to the Dallas Cowboys for another first-rounder, this means Jon Gruden’s team will have three of the top 32 picks in the 2019 NFL Draft.