Exhibit 1 would probably be the inaction of newspaper publishers 20 years ago as Craigslist took the classified ad business away.
Exhibit 2 might be the NYT taking on massive debt 10-15 years ago even as it was pretty clear that their business was changing. Money was cheap and their magic 8 ball said outlook good, so that was all they needed.
Exhibit 3 is probably the lack of care publishers have around the user experience on the web. AMP and IA is Google and Facebook saying "your product is great, your presentation is terrible". A 500 word story should load on a phone in under a second all the time.
Exhibit 4 would be lowering of the editorial bar by lots of outlets. This is probably the big one in my opinion:
* the NYT reporting in the run up to the Iraq war still bothers me, trust is hard to earn and easy to lose
* editors know that there aren't always two equal sides to every story, but that's the format they have
* their interview formats seemed designed so that a question with a yes or no answer can be spun on fly into a statement about something unrelated
* when everything is called breaking news, nothing is breaking news
* the patterns of news outlets are so obvious, that they are easy to manipulate (how many hours of television and lines of print were spent on Obama's birth certificate?)
Exhibit 5 is probably the overly conservative approach to the web. A digital newspaper is the obvious path and it's the only one too many outlets are exploring. Buzzfeed is a nice exception. I don't even think they expect readers to go to their website. Buzzfeed packages everything for sharing and the content flows just about everywhere. I don't think the conservative behavior of most outlets is due to lack of ideas. Some very smart people (like Dave Winer and Jonathan Abrams) have expressed a lot of interesting ideas that nobody seems to be willing to experiment with.
A decent amount of shrinkage in the news business was overdue. If you travel and read local papers, they are all almost exactly the same. If you watch local evening news, every program has the same format and basically the same set. There's a ridiculous amount of duplication and redundancy and getting rid of that frees up a lot of resources to work on other stuff. Fortunately, I think the shrinkage is mostly complete.