One of the persistent issues with the Chicago Bears over the past decades is their tendency to act like a small market franchise in a big market. The McCaskeys run the team as if it were still the 1960s when spending money was dangerous. That meant being extra cautious with player contracts and never shelling out resources for head coaches or general managers. It is part of why George Halas chose to coach for as long as he did. As the owner, he wasn’t required to pay another coach a hefty salary.