Bolles School

by Tim Gilmore, 9/30/2021

1. Florida Castle Boom and Bust

Now rose, with the sun, the San Jose Hotel, 1920s, on the bluff above the river where the slaves of Francisco Xavier Sanchez worked cotton in the late 1700s.

In homage to Spanish land grants here from before the United States was a nation, hoteliers charged architects Harold Saxelbye and Mulford Marsh with creating the likeness of an “ancient Spanish castle.” It took less than three years for one of the grandest new hotels in Florida to go bankrupt. Few people at the height of the ’20s Florida Real Estate Boom, which proliferated “Mediterranean Revival” style mansions and hotels across this southernmost state, could have imagined how completely and quickly the U.S. economy would collapse.

The Florida Times-Union describes opening night, for which 600 workers built the San Jose Hotel in six months, 125 rooms, 1926, as a “brilliant gathering” like “unto the courts of Spain with all of its splendor.”

2. Sell Yourself a Hotel

The San Jose Hotel opened on January 1, 1926 and almost immediately began to fail. A quick series of mortgage transitions brought it down into one woman’s hands.

Her name was Agnes Cain Painter. Former secretary to deceased real estate tycoon, swindler and millionaire Richard “Dicky” Bolles, Agnes held the hotel’s first mortgage. In ’27 she took out a mortgage for the hotel’s furnishings. In ’28, she filed for foreclosure and bought the hotel outright herself.

If those first moves, from mortgage to foreclosure to full purchase, looked like a shell game, that was nothing to what Painter did next. She formed a corporation called the Bolles Investment Company, elected herself president and her new husband, who was almost 30 years her junior, secretary, then sold the hotel and its furnishings to the investment company she’d just formed.

She issued shares to herself and the Richard J. Bolles Estate, then leased the property to the Florida Military Academy. And so the San Jose Hotel first became an educational institution.

3. Announcing the Bolles School

Agnes and Roger Painter lived at the castle while the military school paid rent. They walked at will between the arches of the arcades and stared from rare heights above a St. Johns River shoreline. They dallied in the lobbies of rich dark masculine oak and pecky cypress, beneath ornate corner towers with high clay arches beneath red roofs. Through the long walkways, they saw the sun dance lambent on tens of thousands of ripples of river at once. Not all the tourist rooms had been converted and the Painters could trace with their fingertips hearts skewered with arrows hand-carved in high windowsills. Any moment they so desired, they could stand in the colonnaded peaks of the four story towers on either side of the front central courtyard.

In as short a time as the San Jose Hotel had failed, the Florida Military Academy followed. Summer of ’32, the Painters gave the school notice of eviction by the end of the year. A local attorney friend suggested they start their own military school, so today the entrance gates to the Bolles School, one of the most prestigious private preparatory schools in Florida, date its foundation to 1933.

The Painters, who had no teaching or school administration experience, no pedagogy and no military experience, named the school for their former boss.

4. “Flimflam” Philanthropy

But oh the story Agnes’s long servitude to Dicky Bolles told—whether or not she were Dicky’s mistress; whether or not she ruled with an iron fist over her new husband, three decades her junior, in Dicky’s name; whether or not the ethics of her ventures invited as much scrutiny as those of Richard Bolles had!

A New York businessman born in 1843, Bolles launched money-grubbing schemes as far away as Colorado and Oregon before heading to Florida in 1908. The Florida Internal Improvement Fund sold Bolles half a million acres for two dollars per, agreeing to use half the sale proceeds to drain land in the Everglades, and making Dicky Bolles only the second million dollar Florida land buyer.

So Bolles began selling, via long-distance auction, Florida swampland as farmland down in Dade and Palm Beach Counties, then higher up around Lake Okeechobee. His salesmen crisscrossed the country, promoting land underwater in the Everglades as “the Garden of Eden” and “the Promised Land.” They said nothing about the State draining the swamp sometime in the future.

In 1913, when news of the full scope of the operation got out, bidders sued. Two years later, courts allowed Bolles to keep the $1.4 million of his profits—one headline said, “Bolles May Keep the Boodle”—but prevented him from selling any more land from the Everglades.

Federal authorities brought the next big case against Bolles, representing 12,000 purchasers of subaquatic Florida farmland from across the country. Bolles was arrested in December 1913 and tried in March. His salesmen, he claimed, had only misrepresented “the land they sold” because they were “misled by officials of the State of Florida and officials of the United States Department of Agriculture.”

In a 1997 South Florida Sun Sentinel article called “Psst…Wanna Buy Some Swamp Land?” staff writer Robin Fields told “A History of Fraud, Flimflam and Finagling.” A playful photo caption explained, “Richard Bolles and friends sold underwater ‘farms.’ Buyers got soaked.” Wrote Fields, “Buyers paid $240 for ‘farms’ in the Everglades,” but “Once the buyers realized most of their land was swamp, Bolles was indicted. He died before trial.”

When Bolles died in 1917, his personal secretary, Agnes Cain, who’d served Bolles dutifully since first joining him in his mining ventures in Colorado, took over his estate. Meanwhile, headlines proclaimed, “Widow of Millionaire Bolles Entirely Ignored in His Will.” Susan Thompson Bolles of San Francisco sued unsuccessfully to prevent her late husband’s will being fully executed.

The year before his death, Bolles had hired an office boy named Roger Painter for four dollars a week. Though Agnes was 27 years older than Roger, the two married in 1923, carrying on Dicky Bolles’s business under Agnes’s rule. When they formed the Bolles School a decade into their marriage, Roger became school president, though Agnes ran the school.

After the couple’s brief foray with the Florida Military Academy, the State of Florida agreed to grant Roger a “special dispensation” as honorary Florida militia lieutenant colonel, so later Bolles School promotional material referred to “President and Founder, Colonel Roger M. Painter.” It referred to Richard J. Bolles as a “philanthropist.”

In his 1983 book Bolles: The Standard Bearer, Jacksonville University English Professor George Hallam wrote of the Bolles School as the crossroads of a “failed hotel” and “controversial namesake,” a man who wrote in his own journals, “I am in nearly every business and social transaction guided almost entirely by impulse, with no fixed principles.”

5. Oh He Was a Beautiful Boy

“Oh he was a beautiful boy back then,” Margaret Fisher recalled. And she was with him at the end. He fought off his depression at the stone gazebo, armed with guitar and poetry. The river undulated and scintillated and shone like broken glass or a plane of diamonds. “I tried to be as far from him as I could get,” said the doctor’s daughter. “He was playing his guitar and performing,” but she was burying her face in Truman Capote’s glorious first novel, Other Voices, Other Rooms.

Bolles still functioned as a military academy in 1958, four hours of academics in the morning, military training and athletics after lunch. The Old South ideal of military training for manhood bled into Bolles’s focus on athleticism even after the school left its military training behind in ’61. Gram Parsons’s time at Bolles spanned the transition.

Ingram Cecil Connor III, later famous as the musician Gram Parsons, failed at Bolles, transferred to Winter Haven High School back in Central Florida, then shipped up to Bolles again. During his time there, the school switched, in the midst of the Vietnam War, from military structure to the liberal arts curriculum that set it on its current path.

In his 2012 book Calling Me Home: Gram Parsons and the Roots of Country Rock, Bob Kealing quotes Parsons’s advisor at Bolles as calling him “a throwaway kid.” Kealing argues that given what was happening at home, the family’s dumping him at Bolles was “the best thing that could have happened” to him.

The deaths of Parsons’s parents bookended his time at Bolles. His father, Ingram Cecil “Coon Dog” Connor II, killed himself two days before Christmas, 1958. Gram was 12. When his mother Avis remarried shortly thereafter, Gram took the name of his new stepfather, Bob Parsons. The day Gram Parsons graduated in 1965, Avis died of cirrhosis from years of alcoholism.

At 17, Gram Parsons was singing for a series of Valentine’s Day concerts with a band called the Shilos. When he crashed back into the quad and towers by the river, he wrote, February 17, 1964, to Marilyn Garrett, “The sun is setting over the river and I’m depressed. When I’m depressed, I have to talk to someone. You’re elected!”

He fell for Marilyn. His grades suffered. He wrote that “prep school” was “sterile.” Meanwhile, he played with the Shilos as far away as Chicago. Writes Kealing, “The contrast couldn’t be more striking: to the lily-white provincial children of staunchly conservative moneyed parents, Gram brought tales of singing alongside the messengers for integration and civil rights.” He read Ferlinghetti, hung around downtown on weekends, he and his friends coaxing “winos” to buy them liquor in package stores, partied and played guitar at the Mayflower Hotel.

Whether or not Gram Parsons, and whether or not the Rolling Stones’ Keith Richards had turned him on to it, committed suicide via morphine and alcohol, 26 years old, perhaps no one can say definitively. More definitively, Mick Jagger wrote the song “Wild Horses” for and about Gram Parsons.

Margaret Fisher, who’d first grown enamored of Parsons at Bolles when it was an all boys school and she was 12, joined him that final September when his multi-day bender ended with him dead in the Joshua Tree Inn at Joshua Tree National Park, California, Gram Parsons’s personal totem landscape.

6. Intro to Women’s Studies

Echoes of Bolles’s military tradition survive in the legacy of its transference to athleticism. Bolles is proud of its winning football seasons, its more than 400 wins under Coach Charles Buxton “Corky” Rogers IV. Over the decades, when its sports teams did lose, families from other schools heard the chant, “It’s alright. It’s okay. You’ll all work for us someday.”

During “Activity Hour,” after first and second period classes, Dylan wandered across the nearby golf course to the condos where his friend Asher lived and the family maid fixed them a big breakfast. Then they’d smoke a joint beneath the magnificent oaks and wander back to school.

Into this culture in the fall of 2001 stepped Laura Jeffries, who taught at Bolles for three years. She remembers the student who responded to The Great Gatsby with the trickle-down slogan, “But the rich need the poor!”

What sent Laura packing was the school’s response to her proposal to teach a Women’s Studies course, a response she recognized 16 years later when the Bolles School made headlines for ditching a proposed diversity curriculum after five former board chairmen sent the current board a letter warning the loss of financial support.

Though she won service awards and received merit raises, Laura says frankly, “I did not like much of what I saw there.” In her third year, “The administration asked faculty to propose new courses that would line up with introductory subjects or common majors in college. So,” she says, “I wrote a general plan for an Introduction to Women’s Studies course.” Other pitches included courses in psychology and the Civil War.

In the spring of 2004, even as students began to enroll in the class for the following fall, news of its demise reached Laura in the form of a private warning. A couple weeks later, when Principal Matt Walsh told Laura the board had decided the topic was “too specific,” she pointed out the board “did approve a course about one single war.”

Laura pressed on. Walsh admitted the board felt the course “did not align with the school’s values.” When Laura pressed further, Walsh said the board saw a conflict between Judeo-Christian values and the teaching of women’s studies. “Bolles is not marketed as a Christian school,” she says, “and certainly not as a variety that would preclude teaching women’s studies.” She’d told Walsh she would never have taken the job if she’d known the way Bolles made curricular decisions. That fall, she took a position teaching English at Florida Community College at Jacksonville.

She’s glad to see the school’s website says it now offers an African American Literature elective, but wasn’t surprised when Bolles made headlines by nixing a racial literacy program that made its wealthiest donors feel threatened.

7. Angst, “Sub-Groups” and “House Slaves”

“Pollyanna” seems an ironic name. From Eleanor Hodgman Porter’s 1913 children’s novel and subsequent Disney movie, the word now generally means a foolishly optimistic person. Was it Pollyannaish to expect the Bolles School to implement a curriculum that would “encourage and enhance racial literacy, geographical awareness, and cultural competence both in the classroom and throughout one’s life”? That’s what Pollyanna, a nonprofit organization that helps institutions achieve their DEI (Diversity, Equity and Inclusion) goals, says its curriculum does.

Bolles killed the new curriculum when five of its board’s former chairmen sent its current board of trustees a letter, warning that the school’s financial support would be in jeopardy if Bolles began, in their words, “promoting any sub-group based on religious beliefs, skin color, ethnicity or sexual preference,” secure that, at least at Bolles, their own group wasn’t “sub-.”

In sending Pollyanna out the door, the board cited “angst,” and the small Black Bolles Alumni Group, in a public statement, asked why the “angst” exhibited in testimonials of racism from the classes of 2002 through 2020 at the “Black at Bolles” Instagram account mattered less than that of Chester “Chip” Skinner III or Clancy Houston.

Several former students posted at “Black at Bolles” about having to read “the n-word” aloud from Huckleberry Finn in Bill Hillenbrand’s English class, even as the teacher wore Confederate flag suspenders. Each was the only black student in class. “Every time a white student would say the ‘n-word,’ they would giggle and look at me.” Another student heard a group of white male students telling “Dean Newman” they were flying Confederate flags on their vehicles “to piss off the libs.”

History classes “glossed over slavery,” often claiming it had nothing to do with the Confederacy or the Civil War. One student was told that black Bolles students weren’t “niggers,” but that most other black people were. Furthermore, black Bolles students were like “house slaves,” while other black people were more like “field slaves.”

“Mr. Newman,” one student writes, “caught this Alex kid calling me a nigger out loud in front of everyone.” The punishment? “Extra stairs at football practice. The football team blamed me for it!” Other students remembered the “Fab 5” and “Ortega crowd,” who “used to say the most racist things,” then ask, “What are you going to do about it? Do you know who my dad is?” An advisor told a student she should only apply to HBCUs (historically black colleges and universities) because she couldn’t get into PWIs (private white institutions).

Perhaps some of their parents remembered the outcry in 1991 and ’92 over comments made by Judge John Santora, who’d been a circuit court jurist in Jacksonville for 30 years. The situation brought the Reverend Jesse Jackson to town on three separate occasions, holding rallies and demanding the judge be removed from the bench. Santora had spoken out against minority judges, interracial dating and school desegregation. In an interview he’d given The Florida Times-Union on December 11th, he said, “They also have blacks at Bolles, but those blacks are disciplined. They don’t molest teachers. They don’t rape.”

“Angst,” said Peter Whitehouse in a Florida Times-Union guest column, “is a powerful and telling word choice.” Whitehouse taught American History and Government at Bolles for 15 years. Would this state of angst, he wondered rhetorically, “be an examined world, one in which difficult subjects are raised, researched, and discussed in the hope of better understanding them? A world that had decided that the origins, power, and effects of such subjects needed to be brought out of the shadows, identified and, where necessary, addressed? A world committed to understanding and knowledge? A world very much like a school?”

Whitehouse referred to Bolles parents who opposed the teaching of evolution, a science teacher who offered presentations to parents on why he didn’t believe the science of climate change, and a student who quoted his father as saying black people were “better at sports” because they have “an extra muscle in their legs.” He mentioned the “casual racist comments” made “at school events and in the hallways.”

“Bolles is a place where white privilege is the default,” Whitehouse wrote. “I recognize it in part because I attended a similar school myself and acknowledge how I benefited from that privilege and my luck to be born into an affluent, white family.” He argued that “self-examination is usually difficult,” but that it’s the responsibility of a “demanding academic environment.”

If a private prep school’s goals also include the maintaining of status and entitled privilege, however, does resolving the clash of such interests become more difficult than those vested in its raison d’etre might be willing or able to achieve?

8. Wandering Where I Don’t Belong

It costs more to send a child to Bolles for one year than it does to earn a bachelor’s degree nearby at the University of North Florida. Bolles has graduated Olympic swimmers and professional football and baseball players. Its graduates head for Ivy League schools.

Surely Bolles has hosted many a John Keating, the unorthodox English teacher played by Robin Williams in the 1989 film Dead Poets Society, but there’s no evidence it’s produced a Patrick Bateman, the prep school graduate, Wall Street investment banker and killer who narrates Bret Easton Ellis’s 1991 novel American Psycho, played by Christian Bale in the 2000 movie.

Strange to have these halls mostly to myself this afternoon. I don’t belong. I, son and grandson of farmers, grandson of sharecroppers. I, whose parents shared a single old Plymouth gas guzzler when I was little. Here, I launch depredations on memories from heavy dark masculine wooden rooms from long before I was born, gather my spoils, arrange them into this story.

Education means, to me, more than anything, a series of epiphanies that rewire your brain and charge your heart to make you more you that you ever were. It makes you conscious of the world, of its connectedness, of your place in and responsibility toward it, of your own agency in the all-as-one. Yet education, so often instead, at the end of a pseudo-academic conveyor belt system, a millwork of Industrial Revolution Scientific Management, seems the packaging of the class-based product you were, from the very beginning, whether rich or poor, intended to be. These two definitions oppose one another.

Late afternoon sunlight plays in the strange plaster shapes on the walls of the towers. What I think here does not matter. Green and gold and blue fleckstones bounce light back as I approach the river. The Corinthian columns supporting the arches of the colonnades stand staunch. Tongues stick out between the plaster acanthus leaves. Fratboy slapstick pratfalls ensue, presumed descended ancient Athenian.

Ancient oaks, one nearby called Father Time, adjoin the tall towers. I hear the music of a military marching band, distant, folded into the wind. I smell new loves at ballroom dances. I wouldn’t deny anyone the chance at the best education. (I can’t.) No more than I can deliver it to those whose lives orchestrate themselves otherwise. (I’ll not stop trying.)

Meantime, ghosts of opportunities never realized, ghosts never realizing they existed, lurk behind Christmas trees by redoubtable hearths, or Christmas trees two stories tall in the courtyard, in 1943 and ’56 and ’74. Young lives walk hand in hand in self-discovery like the center of all the world. Debate teams and key clubs and intramural boxing. The class of next year will ask itself what Bolles it wants to be, and to what extent its choices can be achieved.