I think Esolen's premise is here to pretend to teach children something boring them in the process. Then, you won't have to work so hard to bore them or teach them, because they'll have already tuned you out. And I think schools often do this; not necessarily as intentionally as Esolen is describing. I was a "good" student in a "good" school, and learned things my peers claim to not have learned, but I am certain there is a lot I tuned out on because I was told it wasn't interesting or was unnecessary ... never in so many words.
I do like, however, his continual hopefulness that learning doesn't happen only in the classroom and that many children will try to learn through what catches their fancy. This will be perhaps a very focused and unbalanced learning, but figuring out how the telegraph works by making one, playing with baseball stats, or grammar ala Tolkien will keep the possibility of the imagination alive ... maybe for one spark.
I appreciate his insistence on structured learning being necessary for true imagination: that memory work, basic arithmetic, and grammar are necessary tools for skill to leverage content into imagination.
We do a lot of Memory Work (some which isn't even listed in our Weekly Reports). We do memory work to exercise the memory, put interesting phrasing and language into our common family language, and to prepare our students. Last summer I read Leigh Bortins' The Core and one of my major take aways is that memory work gives students content to work with ... giving them something to think logically about and then to expound upon. If we want to prepare our children to be clear communicators and clear thinkers; memory work is a foundational tool in this preparation.
The same can be said for math and grammar as they're applied.
This post is for Cindy's Book Club on Ten Ways To Destroy the Imagination of Your Child. Go there to read posts by other, more eloquent and smarter people than I am :)