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The Headmaster's Dilemma

3.15  ·  Rating Details  ·  124 Ratings  ·  24 Reviews
In The Headmaster’s Dilemma, Louis Auchincloss revisits the prep school world of his most famous novel. That book, The Rector of Justin, published in 1964, took the form of a fictional biography, giving the reader the full life story of a much beloved and revered, if also feared, headmaster of an exclusive New England prep school. In The Headmaster’s Dilemma, we see up clo ...more
Hardcover, 192 pages
Published September 10th 2007 by Houghton Mifflin Harcourt (first published January 1st 2007)
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Dec 03, 2007 Phyllis rated it liked it
Recommends it for: educators
This novel takes place in a private prep school in New England, where the author once again uses his incisive rapier wit to burrow into the characters' fears. There are two stories: that of the high-school-age boys, and that of the the conflict between the headmaster and the major donor, a mean though generous (for his own aggrandizement) philanthropist.
For those of us who went to public schools, it is sa to see how the denizens of boarding schools can be so mean to each other....
Jan 20, 2008 asra rated it liked it
Shelves: novels
Except for the terribly abrupt ending, I liked this book and the take that it has on high-society. Reminded me of a quotation I heard once: that people will admit to felonious crimes before they will admit to envy. This book is about how political maneuvering finds foundations in tendencies such as envy and hypocrisy. Auchincloss's depiction of the envious Donald Spencer was enough for me to appreciate the novel.
Feb 19, 2016 Mark rated it it was ok
Shelves: fiction
I hadn't read any Auchincloss in ages, and knew him mainly as the scribe of the moneyed classes of New York.

From this point on there will be some spoiler alerts in order to explain the review.

My feelings about this book can be boiled down to one summary: this was a book written a generation too late, by an author of a previous generation. In this novel, Auchincloss returns to a previous setting, the prep school of Averhill, where golden alum Michael Sayre has become headmaster, and finds himsel
Apr 17, 2016 Trudy rated it it was amazing
Very enjoyable. I'm surprised this is not on a best seller list!
May 26, 2015 Stacey rated it did not like it
Just not really my cup of tea. Kind of dense and dated. I was actually surprised just now to see another review saying it was set in present day because I definitely thought of it as the past when reading.
May 02, 2009 Bonnie rated it liked it
A novel of manners exploring the Manhattanite WASP world into which Louis Auchincloss has lived his 91 years. His sexual politics are what one might expect of an author born in 1917. Although the novel is set in the present day, I felt as if I was reading a piece of historical fiction, describing some lost time in the 20th century. Valuable to have his insights into the world in which he has moved, even if it did not make for a convincing contemporary drama.
Feb 03, 2012 Sabrina rated it liked it
At first I wasn't sure I was going to like this book. The characters and the settings were foreign to me and their beliefs and interactions seemed antiquated. However, while this feeling didn't go away during the book the story did become more compelling and the characters slightly more interesting. Overall, a decent and quick read which leaves you contemplating the situation, characters and outcome.
Aug 16, 2011 Sparrowfall rated it it was ok
I did not find the characters believable at first. To the author's credit, however, he continued to develop them to the point where I eventually accepted their world and their antiquated language and behavior. I just didn't care for that world or the events in it, mostly because the main plot line came about and ended artificially and implausibly.
Jun 04, 2008 Ginny rated it really liked it
A story about the relationship of the headmaster and his trustee chairman, all colored by their days as schoolmates, and the successes of both men. When the headmaster's job is threatened by a situation with two boys at the boarding school, it looks as if he will lose everything. And the crisis is averted in a very unexpected way. Entertaining read.
Feb 26, 2009 Cera marked it as grazed
I've mostly read really old Auchincloss, pre 1970s, so it'll be fascinating to read his most recent novel & see what he's making of today's world.


Okay, I don't think I *like* what he's making of the modern world, which seems to be 'it's not rape if you enjoy it, and anyway, why make a big fuss about it?'

Jerry Delaney
Jul 30, 2009 Jerry Delaney rated it did not like it
This book's dialogue reads as though it were written in 1922. I kept forgetting the time period in which it was actually set because everything was so anachronistic. I wanted to like it because I felt the author's heart was in the right place. But I couldn't.
Mar 10, 2013 Allison rated it it was ok
The story for this was fairly mediocre. Although well written, it was incredibly dry and had an overwhelming feeling of trying too hard to be a thought piece on the motives and curiosities in human nature.
Apr 20, 2010 Heather rated it liked it
Shelves: 2010
An interesting look into the politics at a private boarding school, and how so many outside factors can weigh on the outcome of what should be just a student's disciplinary action. A very quick read.
Jun 26, 2008 Laura rated it liked it
While Auchincloss is not at all "beach reading," I always treasure his books as a little bit of fun reading about the life of the privileged in and around NYC. This book was no exception.
Feb 18, 2008 Doug rated it it was amazing
I didn't expect much from this novel, so I was pleasantly surprised at how well written and interesting it was. What a great novel from a well established author.
Donna Kusuda
Jul 30, 2010 Donna Kusuda rated it liked it
Had always heard about this author and had never read him. Very good story about marriage. Would probably read more of this author.
Coco Torre
Oct 13, 2013 Coco Torre rated it it was ok
All I can think of is that he was really old when he got around to this one. Needed the money? Couldn't come up with anything else?
May 01, 2008 Sarah rated it it was ok
This left a little to be desired...the resolution was really abrupt. At least it was short! ;o)
Cooper Renner
Sep 19, 2011 Cooper Renner rated it liked it
Light reading, essentially. The "inner workings" of a fancy New England prep school.
Aug 12, 2011 Lisa rated it it was amazing
Quick read with a fairly large and complex cast of characters.
Mike Harper
Sep 12, 2013 Mike Harper rated it liked it
Read The Rector of Justin instead. This isn't nearly as good.
Sep 25, 2009 Marti rated it it was ok
sparse outline of a potentially good book.
Jul 28, 2007 Benjamin rated it it was amazing
god this one's a good one!
Jan 11, 2013 Marina added it
Shelves: marina
Freudian drivel.
Jim Ballengee
Jim Ballengee rated it liked it
May 16, 2016
Jeanne marked it as to-read
May 02, 2016
Casey marked it as to-read
Apr 12, 2016
Steven Chang
Steven Chang marked it as to-read
Feb 12, 2016
Jonathan Freed
Jonathan Freed marked it as to-read
Feb 10, 2016
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Louis Stanton Auchincloss was an American novelist, historian, and essayist.

Among Auchincloss's best-known books are the multi-generational sagas The House of Five Talents, Portrait in Brownstone, and East Side Story. Other well-known novels include The Rector of Justin, the tale of a renowned headmaster of a school like Groton trying to deal with changing times, and The Embezzler, a look at white
More about Louis Auchincloss...

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