The general manager was in his third year with the Bears, none of which ended in playoff appearances. His 2012 debut stood alone as Chicago's only winning season.
Emery replaced long-time general manager Jerry Angelo, who led the team to a Super Bowl back in 2006.
The general manager's difficulties extend far beyond one bad contract, though. Emery opted to hire Trestman over current Cardinals coach Bruce Arians, who will almost certainly win the NFL's coach of the year award. He also irked multiple people in the building, Rapoport noted and wasn't known as an executive who fostered a professional atmosphere.
A once-stable offense seemed to peak during Trestman's first season before crashing to earth as well. Cutler, whose seven-year, $126.7 million contract hampered the Bears financially, could not dig Emery out of such a significant hole.