#5. Michael Bennett, DE
In late October of last year, the Cowboys were looking to add some punch to their defensive line. So Dallas traded a conditional seventh-round selection to the New England Patriots for three-time Pro Bowl defensive lineman and Super Bowl-winner Michael Bennett.
In nine games, Bennett was effective recording 27 total tackles and 4.0 sacks playing both at defensive tackle and defensive end. Unfortunately, the Cowboys would end up losing five of those nine games including a critical Week 16 matchup against their divisional rivals, the Philadelphia Eagles.
Now 34-years old and scheduled to become an unrestricted free agent next month, it seems unlikely that the Cowboys would re-sign the aging Bennett who had a combined salary of over $8 million in total cash in 2019 according to spotrac.com.
In a recent interview with fanaticsview.com, Bennett was asked about his possible future in Dallas. The veteran’s response was that he has no idea and it’s all on the Cowboys. Unless Bennett is willing to take a very team-friendly deal, it’s hard to envision Dallas retaining him while also keeping big names like Dak Prescott and Amari Cooper in-house.