Ditka...hes done something no other coach in Chicago has done. Won a Super Bowl. Lovie Smith has done something only one other coach in Chicago has done, gotten to the Super Bowl.
Should the 80's Bears have gotten to more Super Bowls? Probably, but how often do teams in this league win multiple Super Bowls? Teams like the Ravens had a great defense and statisically better than the 85' Bears, and they only won once. Injuries are usually the cause of a team not winning another Super Bowl. The Bears lost Jim McMahon in 1986, and started an inexperience Doug Flutie in a playoff game that many of the players questioned. As far as the further demise of the Bears. Alot of it has to do with Mike McCaskey thinking he could rebuild through the draft and then did not have to pay proven players money (This has worked in the case of the Patriots, but the Bears have never really had smart GMs/personnel who can scout good talent minus a few hits here and there). So in all, we needed smarter people near the top to manage the team, and that didnt happen.