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The Headmaster's Dilemma

3.14  ·  Rating details ·  143 Ratings  ·  28 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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Feb 06, 2016 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
Dec 03, 2007 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 07, 2008 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.
Dana Booth
Jun 28, 2016 rated it did not like it
Many, many years ago - when I was a teenager, I went on a summer 1 month research trip with The Explorers Club. My sister learned about it at a science fair and dragged me along. We had a blast and one of the other students was John Winthrop Auchincloss , III or 2nd or 4th or something. We knew his Dad was an author and he was somehow related to Jackie Kennedy. I had a bit of a crush on him and we corresponded a few times that next year when he was at Groton. That was my first introduction to th ...more
Dec 30, 2016 rated it liked it
There is a lot to commend this book. Although set in mid-20th Century New England/New York City, and focused entirely on a power struggle among the 1% over control of a fictional boarding school, it feels really timely and relevant. If I were to teach a course on 20th-C American culture, I might assign it to my students to address how American's continue to talk about class, sexuality, and education. It would also make a great text for expanding one's vocabulary.

A quick read with an uncomplicat
Aug 23, 2011 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.
May 02, 2009 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.
May 27, 2008 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.
Jan 30, 2009 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?'

Alex Tsiatsos
Aug 16, 2011 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.
May 03, 2015 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.
Jerry Delaney
Apr 18, 2009 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.
Apr 10, 2010 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.
Donna Kusuda
Jul 30, 2010 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.
Benjamin Kahn
Mar 25, 2012 rated it liked it
A very slight novel. I like Auchincloss, but there is not much of substance and the plot is very thin.
Jan 11, 2013 added it
Shelves: marina
Freudian drivel.
Mike Harper
Sep 12, 2013 rated it liked it
Read The Rector of Justin instead. This isn't nearly as good.
Jul 28, 2007 rated it it was amazing
god this one's a good one!
Sep 25, 2009 rated it it was ok
sparse outline of a potentially good book.
Jun 26, 2016 rated it liked it
Expected something more wonderful from this prolific and successful author. Don't think I'll try another.
Cooper Renner
Sep 19, 2011 rated it liked it
Light reading, essentially. The "inner workings" of a fancy New England prep school.
Aug 12, 2011 rated it it was amazing
Quick read with a fairly large and complex cast of characters.
Feb 18, 2008 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.
Apr 28, 2008 rated it it was ok
This left a little to be desired...the resolution was really abrupt. At least it was short! ;o)
Jun 12, 2008 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.
Apr 17, 2016 rated it it was amazing
Very enjoyable. I'm surprised this is not on a best seller list!
Coco Torre
Oct 13, 2013 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?
Nikki Muraca
rated it really liked it
Jan 02, 2017
rated it liked it
Sep 15, 2010
rated it really liked it
May 05, 2014
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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