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The President’s Letter In 2010 The President Reflects upon the Military Legacy of The Bolles School. One of my great personal joys in my position as president is to attend reunions of graduation classes from 40, 50 and even 60 years ago. Sadly, in many cases these alumni have not returned to the campus since they graduated. Being aware of the significant changes at Bolles since their graduation (moving from being a military school to a college preparatory focus and becoming coed among others), they typically arrive thinking that their alma mater ‘is no more.’ To a man, they reminisce about the academic and disciplinary demands they experienced having prepared them for service and leadership in their careers, many of which have been in the service to our country through military service. They are indeed “members of the Great Generation.” It is exciting to see their perceptions change when they see and hear that, in spite of the significant changes, the important elements of “the Bolles experience,” namely “achievement, service, and distinction,” are still emphasized (and achieved!) here – emphasized in more ways than merely retaining them in the school seal. They are pleased to hear we are continuing to set high expectations for our students, in and outside the classrooms, and are particularly enthusiastic about the examples I share with them of student leadership and service. Most of all perhaps, they take pride in the fact that numbers of the graduates in the ‘college preparatory’ era continue to serve our country through distinguished military service. And as I write this in the summer of 2010, there is no more current or better example of their school continuing its significant military traditions than the example of coed Caroline P. Barlow, the Valedictorian of the Bolles Class of 2007, selected this spring as the outstanding cadet at the United States Naval Academy. She will serve in her senior year as the Brigade Commander – the leader of the Naval Academy Midshipmen – perhaps the most recent example of how the things that were important at Bolles 40, 50 and 60 years ago have indeed been preserved and continue to be honored . We proudly continue the traditions established during the military chapter at The Bolles School, and we proudly salute those who have honored us with their service since their graduation during those years. John Trainer Ph.D.

Rufus R. McClure Rufus McClure arrived on the Bolles scene in 1951 when the school began its eighteenth year, a neophyte fresh out of college. He was a paratrooper during WWII. Following his discharge, he kicked around New York for a couple of years and then, deciding to become a teacher, he enrolled at ASU. Following his graduation, he decided to teach in a military school, which military school was a no-brainer. For the next forty-nine years, he served the school in just about every capacity possible. He taught English in the classroom until 1964, when he became director of studies/academic dean, in which capacity he continued to serve until 1980, when he returned to an earlier incarnation as chair of the English department and taught Advanced Placement English until his retirement in the year 2000. In 2002 he returned as a part-timer, assisting the new president for special projects. This assignment led to the Military Scrapbook. He and Dr. Trainer decided that this Bolles chapter deserved, in fact, required, special treatment. They decided the best way to accomplish this objective in the 21st Century would be to digitize the twenty-nine military yearbooks with appropriate historical and personal commentary. Throughout, the commentary is addressed to you, the Cadet Corps.

Acknowledgment for Clare Lange Since I predate the computer by over two decades, I admit that I am challenged. Therefore, I have depended entirely on the expertise and generosity of Clare Lange, our current librarian and media specialist, for the technology involved in this project. The project would have been impossible without her. Most of us remember the Bolles Library as the gentlemen’s smoking lounge for the San Jose Hotel, all four thousand books. Probably the technology was limited to the pencil sharpener. I hope that everyone who peruses this scrapbook will join me in expressing our collective gratitude for her invaluable contribution to the Military Scrapbook.

Acknowledgment for Geoffrey DeWitt The Bolles School webmaster for his invaluable assistance, for his extraordinary talent, and for his understanding patience in publishing the scrapbook on line.

1934 By Rufus McClure

Preface A Chronological Journey Through the Thirty Annuals that Depict the Life and Times of the Military Chapter of The Bolles School

When I began this project, i.e., analysis of the yearbooks, I expected to present an objective, third person annotation of the most prominent people, events and history. However, as I got into the project, I discovered that I simply could not remove myself from most of the individuals about whom I was commenting because I knew personally most of them and had some personal relationship with many of them. Hence, I often could not resist the temptation to personalize my comments. Therefore, the result is some combination of objective fact and personal memoir. The Companion Text will be published very soon.

For those of you who may not know or, heaven forbid, may have forgotten, The Bolles School was named for Richard J. Bolles, who, having died in 1917, had absolutely no personal involvement in the school. The main building that now bears his name, Bolles Hall, the dormitory, was built by his two closest confidants, Agnes Cain and Roger M. Painter, who, upon his death, assumed control of his vast estate. It was built as an elegant hotel (1925) , the San Jose Hotel, at the height of the Florida boom, just before the bubble burst.

The hotel lasted less than a year. It was then leased to the Florida Military Academy, at that time located in Green Cove Springs. However, this school went under in 1932, at which time Agnes Cain and Roger Painter, now married, decided to found their own school. They did their homework well, and The Bolles School opened its doors as a military preparatory school on January 5, 1933.

The school lowered the flag on the military chapter in June, 1962. However, that final salute did not mean that Bolles had abandoned its military commitment. In the half century since then your alma mater has sent dozens of graduates to West Point and Annapolis, both men and women.

More great news, in fact, fantastic news, about women will appear in the conclusion. Remain alert. You will have an opportunity to render a 2010 salute you could never have imagined when you graduated.

Now, back to the beginning. The first graduation, 1933, witnessed one lone graduate, Sidney Register. The last military class, 1962, witnessed seventy-one graduates, which brought to a grand total of 1455 young men who graduated as Bolles cadets. During these years, dozens of alumni served in WWII, The Korean War, and the Vietnam War, nineteen of whom made the supreme sacrifice. To these men in particular we dedicate this military retrospective, but in a broader sense the dedication embraces everyone who wore our nation’s uniforms or, for that matter, everyone who wore the Bolles cadet uniform.

Probably, the official statement of Virginia Military Institute best exemplifies the military ethic: “It fosters punctuality, order, discipline, courtesy, and respect for authority.”

Ultimately, the military tradition “emphasizes honor, integrity, and responsibility.” Whatever is true for VMI is true for any quality military institution, including The Bolles School..

I have annotated only those items which, in my judgment, explain and advance the narrative. It follows logically that the earlier yearbooks, particularly the first, 1934, require more attention because they present most of the pertinent facts, which do not require repeating in later issues. In fact, the very first yearbook is a treasure trove. Of course, everything in 1934 is a “first� and therefore of universal interest. It is also obvious that most of these first cadets are now lying peacefully at ease in perpetuity since they long ago observed taps for the last time. I have included many pictures that require no comment but which, nevertheless, advance the narrative.

We apologize for the uneven quality of some of the images. Time has taken its toll, and the originals continue to deteriorate. The preservation of this history while it is still reasonably accessible is an important reason for this project. We hope hereby to grasp this history before it fades completely into oblivion.

I admit up front there will be some errors and important omissions, for which I apologize in advance; but I will request that you attribute such lapses to an eighty-four year old memory and not something deliberate. Please advise me of such lapses, and I will correct them. Inevitably, there are repetitions. Many annotations replicate and reference items that appear in the Companion Text which follows. Please enjoy visiting with these first alumni as together you revisit your alma mater.


The first picture of the Color Guard. The building in the background is Grace Chapel, which most of the early boarders attended. Grace Chapel also generated our first service organization, the Chapel Wardens Association, a group of cadets who cleaned and prepared the church for services. Somewhat later Grace also provided the school with a chaplain.

Colonel and Mrs. Painter, the former Agnes Cain, as they appeared at the founding of the school in 1933. They headed the school during these formative years when Bolles became The Bolles School. They oversaw the creation of most of our most cherished traditions. Their footprints are everywhere. Most boarding students will recall their friendly relationships with the student body in this nascent and growing school.

As far as we know, Dr. Lewis was the first person to sign a contract with The Bolles School. As the academic head, he would have been responsible for recruiting and hiring the first faculty, ten, we think. Today that faculty has expanded to one hundred fifty-six, including 26 Alumni/teachers and thirteen part-time alumni, of whom nine hold doctorates covering every discipline. Lewis was also responsible for designing a nascent academic program which is now among the most highly regarded in the nation.

As one of many iconic pictures of the school, this picture of the north tower is probably the most universal. Still today, the tower is photographed, sketched, painted, and otherwise represented more than any other entity on campus. Many cadets will recall pranks committed there, and a few may recall the open balcony at the top as a great place to sneak a smoke.

The very first faculty, a total of ten, only two of whom are in uniform.

Stevens will become a legend; Summers will never be heard from again.

As one would anticipate, the first yearbook contains many photos that over time have become icons. This one is probably the first demonstrable example of a military icon. Today it appears on the masthead of the Bugle, still the school newspaper.

It’s a little hard to believe, but the reality of an orchestra the first year together with the next picture clearly suggests that Bolles wasted no time creating a social scene.

Most cadets will recall embracing their sweethearts in the elegant Bolles Lobby, which, thanks to the TLC of Mrs. John Trainer, wife of current president, Dr. John Trainer, has recently been restored to its former elegance.

Obviously, as this picture clearly suggests, the school very quickly evolved into a striking, smart military unit. Over time Bolles would become the only school in the nation that could boast honor designation in both army and naval units.

As this picture clearly demonstrates, it did not take long to create a governing body, thereby creating a lasting Bolles tradition for developing leaders . Many of the names above became distinguished community leaders.

These seven young men gave us our first yearbook, The Eagle, which, thankfully, provides us with most of the early history that this scrapbook is intended to preserve for all time.

Wow! These young cadets were actually sixth, seventh, and eighth graders. These youngsters would rapidly mature into the cadet corps which we now proudly salute.

Let’s all salute these distinguished young men who were responsible for the success of these early years which laid the foundation for The Bolles School honor military history.

Not quite “Anchors Aweigh” but they are surely on their way.


The first group of swimmers of a program that is now a world renowned swimming program that has produced ten swimmers who have won a collective total of thirteen Olympic medals.

As indicated previously, Captain Register was the lone graduate of that first year, 1933. The following year he was named the first director of the Bolles Alumni Association. Today, his name lives on as the Sidney Register Alumni Award presented at each graduation to a particularly distinguished alumnus. Recipients include Harry M. deMontmollin Class of 1956, who would become the first and only alumnus ever to head the school, 1976-2000. The Sidney Register Alumni recipient for 2010 is the legendary Joe Kittinger, celebrated globally as the first human to enter space when he soared to over 102,000 feet above the Arizona desert in 1959.

Like several organizations cited previously, the band quickly materialized. After all, how can you have a parade without a band? Interestingly, Harry deMontmollin, cited above, was the “Leader of the Band� when he graduated in 1956.

Not exactly a power house at this early date, but this scraggly bunch would mature into the legendary football tradition that is today the proud owner of ten state championships, including the current one last Saturday in the Citrus Bowl on December 12, 2009, three days ago as I write this.

Pictured here is the same Coach Summers responsible for the commencement speech quoted in the next frame.

This text is apparently the commencement address for the first graduates. Although he could not know it, Coach Summers was setting the bar for all time. Few people are now aware of the speech, but its eloquence reverberates through every dimension of school life now as it must have then. Coach Summers never appears again, and there is no mention of him later, so he apparently remained for only one year.

Bolles basketball teams have brought home three state championships since these lads posed for this photo in 1934.

See the love-letter telegram for Christmas in the Companion Text

Most boarding students will recall hanging out at Cohen Brothers on Hemming Plaza, where they waited for the bus to transport them back to school after Saturday leave. This magnificent building, which today is on the National Register, has now been converted into City Hall.


BOLLES MILITARY SCRAPBOOK 1933-1963 BY RUFUS R. MCCLURE The President’s Letter In 2010 The President Reflects upon the Military Legacy of Th...