I believe ubiquitous government schools - especially prizing conformity, rote memorization, and obedience - have contributed to the loss of Americans' freedoms relative to prior generations.
I believe previous generations relied on tutoring and apprenticeship to a much greater degree, and the modern "standardized" model was imported from Prussia (ie the most militaristic and hierarchical part of Germany and Poland) in the late 1800s and early 1900s.