A lot of Boeing's current dilemma is the failure of executive management. A commonly written story is that the competent executives at Boeing, who were focused on solid engineering, were pushed aside by the political McDonnell Douglas executives.
McDonnell Douglas was purchased almost 25 years ago, so perhaps it may be a little unfair to ascribe all of Boeing's current problems to that one event. Still, as an engineer, I can't help but notice executive management operate in similar politically-bent ways at some tech companies I've worked at.