Jerry fails because he's a businessman trying to be a football guy. He makes too many decisions about how it will affect his bottom line and not how it affects the team's ability to win. Jerry has squandered opportunities and has a habit of neglecting areas or thinking it's good enough, even though it's obviously a weakness that will cost games. Defense has always been an issue, currently it's DL and being able to stop the run and that's been a problem for awhile. Before this defense, we knew we were screwed if Sean Lee, aka Glassman, got injured and well of course he would get injured. The trenches always seem to be an area of neglect, whether it's offense or defense, not flashy and marketable enough, who cares if the base success of the flashy positions come from controlling the LOS.
Jerry's arrogance or ignorance always seems to cost the team. 500 coaches can win a Superbowl with this team, yeah as long as it's Jimmy's team. Hey, we're so good, let's have a Special Teams draft. We don't need a #1 WR, we'll be fine with a bunch of jags, that worked out well. We can just use jag RBs again because it worked out so well after Demarco Murray left, getting Zeke the first helped fix that one, but will getting Zeke a second time help? Jerry likes to blame the cap and it's fashionable to blame the players for wanting to get paid, but it's Jerry's decisions that put the team in these positions.
There is no accountability on the football side, a football guy is measured by wins/losses and playoff success, but the businessman is measured by the bottomline. Jerry can say he wants to win, and in truth he is winning, he has the most successful sports organization in the world. Jerry fails because as long as the money keeps rolling in, there is little motivation to change the part of himself that wants to be a football guy.