Butterfly in the Typewriter

Returning to the realm of brick and limestone, Toole found little had changed in Manhattan since he’d left. The skyscrapers still towered over the people who still hurried along sidewalks. The bohemians of Greenwich Village still gathered in Washington Square Park. The Beats still preached their anti-establishment message in cafés and dive bars. And Columbia still held its regal poise in Morningside Heights. But Toole had changed. As an experienced instructor, he could now manage a classroom, not just ace a course. And the terms of his survival in Manhattan had changed, too. No longer under the wing of the Woodrow Wilson fellowship, Toole intended to work while attending Columbia part-time until he earned his PhD, which would take at least three years—three years of bouncing between the west and east sides of Manhattan. With the pressures of earning enough money to survive and his rigorous daily routine, it would be a year vastly different from his first foray to New York City. And yet there remains a mirrored dynamic between those two years. They both began with his initial excitement but led to his eventual dismay with a place that he found hard to love at times, despite his best efforts. And at some point in the midst of his mind-spinning schedule, he would begin sketching his ideas for what would become A Confederacy of Dunces. It was to be Toole’s busiest year. For the first time he took on the roles of student, teacher, and writer all at once. And after donning all three hats that year, he would leave New York with a clearer sense of what he wanted to do, what he had to do with his life.

He began his semester with intense focus on his studies. He rented a “large and bright” room on Riverside Drive, which offered him “a limited view of the Hudson and New Jersey across the river.” He registered for four graduate courses, a daring endeavor in combination with his new teaching post. And while his courses were all on aspects of British literature, he selected ones that reflected his expansive interest in various time periods of history. He registered for a course with William Nelson, the same professor from his MA studies who read The Faerie Queen aloud. Under the guidance of the energetic Jerome Buckley, he studied Charles Dickens in Victorian Prose and Poetry. And he took a seminar on the Augustan satirists with James Clifford, a course aligned with his creative interests as a humorist more than it was with his academic pursuits. In this class he likely encountered the epigram by the master of satire Jonathan Swift:

When a true genius appears in the world,
You may know him by this sign, that the dunces
Are all in confederacy against him.

Again taking his seat in the lecture rooms of Philosophy Hall, listening to erudite professors postulate on form, genre, and aesthetics, he had resumed his place in the city he so desperately craved. “He loved New York, and he loved Columbia,” Patricia Rickels remembers. “He wanted nothing more than to return.” Yet, unexpectedly, Morningside Heights proved quite sedate compared to his post at Hunter College on the Upper East Side. In the fall of 1960 the affluent neighborhood became a stage for the Cold War capers of the premier of the Soviet Union, Nikita Khrushchev. On September 19, the first day of classes at Hunter, Toole approached the campus on Park Avenue to find police had barricaded the road and posted guards in front of the Soviet embassy across the street. The security detail remained for several weeks, keeping watch over Khrushchev, who was in New York to attend the United Nations General Assembly. The New York Times reported that classes at Hunter remained undisturbed by the presence of the Soviet leader, but the calm did not last. As Toole reported home, “Refugees from communist controlled countries in Europe demonstrated here every day, screaming, singing, chanting. . . . ” The refugees acted on the fundamental American freedom to protest, an act that may have resulted in execution in their homelands. But the civilized residents of the Upper East Side, accustomed to the serenity of their corner of Manhattan, found the protests bothersome. Toole observed how they “retaliated (in the cause of quiet and order) by pouring water from their apartment windows onto the demonstrators below.” From September to October, as Toole watched the comings and goings in and out of the Soviet embassy, he saw the key players that would throw the United States into the most intense years of the Cold War—“Krushchev [sic], Malenkov, Kadar, Castro, and the others in their clique.” Abandoning the decorum of diplomacy, Khrushchev made headlines with his zany antics. Upon hearing “The Star-Spangled Banner” blaring out of an apartment window, which was obviously timed for his passing by, he stopped on the sidewalk and moved his hands in rhythm like the conductor of an orchestra. And he made a desperate attempt to derail a United Nations session when he removed his shoe, “brandished [it] at the Philippine delegate on the other side of the hall” and then “banged the shoe on his desk.” Initially humored by the insane behavior of Khrushchev, Toole expressed an underlying sense that the “carnival atmosphere . . . could have, of course, erupted into something more serious.” Most New Yorkers, particularly those living near Hunter, were eager to see Khrushchev go and their lives returned to normal.

One morning in mid-October, Toole found the police barricades removed. The departure of Khrushchev had “restored peace” to the Upper East Side. And feeling optimistic about his place at Hunter, he sat down in his twelfth-floor office, with its nice view of Midtown Manhattan, and wrote a letter to his Aunt “Nandy” and Uncle Arthur, detailing his current situation in New York. He compared the appearance of Hunter to Charity Hospital in New Orleans in its “institutionalized aspect” remnant of “the late 1930s.” He conveyed the intrigue of Khrushchev and the demonstrations that took place in the streets. And he described his first impressions of his students, who had far more potential than what he encountered in Lafayette. He reports,

The students here are—for the most part—very sharp, very eager and interested, very worthwhile. The all-girl student body is principally Jewish and Irish, balanced in about a 50-50 split, and all drawn from the New York metropolitan area. I’m teaching a Dominican nun, Sister Martha.

To a new arrival, Manhattan can create an odd sense of alienation as one finds his way through the throngs of people constantly moving toward some unclear end. Toole confesses, “I find that I must readjust to this maelstrom after my leisurely stay on the Bayou Teche.” Longing for some Southern warmth, he contacted a few fellow Louisianans living in New York at the time. When Toole told Mario Mamalakis—Nick Polites’s aunt and a librarian at SLI—of his return to New York, she suggested that once he got settled he call Clayelle Dalferes, a native of Lafayette. So, Toole called Dalferes one afternoon, waking her from a nap. She picked up the phone, and before Toole could say a word, she sleepily asked, “Is this business or pleasure?” Toole thought her greeting “was hilarious,” Dalferes remembers. “He never let me forget it. He repeated the phrase to me throughout our friendship.” Together they went to movies, browsed bookstores, and dined. On one occasion she ate lunch with him at Columbia, and she was struck by how he “treated women in the cafeteria the same way that he treated professors. The women loved it.” Even amid the masses of New York, he remained “very much a Southern gentleman.”

Toole also contacted Emilie Russ Dietrich, who had shared that impromptu dance with him during Mardi Gras in their Tulane days, a moment impressive enough for her to remember how talented a dancer he was. She was living and working in New York City, so Dietrich joined Toole at movies or at the Roseland Dance Hall, where people danced “cheek to cheek” to the tunes of big band jazz. And one night they went to Harlem—an adventurous outing for two white Southerners in the early 1960s—to see “Moms” Mabley perform at the Apollo Theater. That night they were welcomed to that shrine of African American performance art. And they laughed at comedy derived from the African American experience. And, of course, they had engaging conversations. Dietrich (now Emilie Griffin) fondly remembers, “Toole’s way of smoking his cigarette hidden behind his hand and his way of talking without looking straight at you, but smiling a little superior smile.” There must have been a certain comfort Toole took in exploring New York with his friend—they were in an exciting place that could quickly become lonely and cold without fellow companions with similar sensibilities. In a letter to her mother in late November, Griffin confessed that she “just had one of the funniest phone calls ever with Ken Toole.” As she remembered, he spoke with speed, and his humor was just as quick. She explains what it was like to be in his company:

With great skill and without warning, Ken would move from being a “colored cat” to being what New Orleans people now call a “yat” (as in “Hey, dawlin’ where yat?”), jumping from one impersonation to another with little explanation. I was expected to follow him. I was supposed to know. Moments later, leaving me in stitches, Ken would return to his own character, asking me if I wanted a Coca-Cola or if I wanted to dance.

In November, when he spoke to Dietrich with such spirited hilarity, Toole had reason for excitement. A few days after presidential candidate Richard Nixon paraded down Broadway while celebrants threw paper streamers into the air, his opponent, John F. Kennedy, was announced the next president of the United States. Toole wrote to his friend Joel Fletcher months later, feeling encouraged about the new president with whom he shared a similar name and religious identity, “It looks as if Kennedy may justify my faith in him, although I’m only very grateful that we were spared Dick and Pat.” For the first time in American history, a Catholic with Irish roots would hold the highest office in the nation.

Socializing with a small circle of friends and appearing hopeful over the future of the country, Toole enjoyed the “cool, clear autumn” of New York. In fact, it was that same season in New York that the iconic film Breakfast at Tiffany’s was shot. In mid-October of 1960 Audrey Hepburn was spotted throughout the city shooting the adaptation of the novel by New Orleans–born writer Truman Capote. On one occasion a crowd gathered as Hepburn walked to a window in Tiffany’s on Fifth Avenue, wearing “a stark Givenchy evening gown.” The crowd appeared disappointed that it was not a jewelry heist or Khrushchev in one of his curious episodes. But once released, Breakfast at Tiffany’s crystallized the glitz and glamor of New York for millions of Americans. It presented a bedazzling city, where writers and elegant socialites walked the streets in the latest fashions, all set to the backdrop of the city in the fall of 1960. It was a vision of the city Toole would have loved to live. But after eight days the cameras stopped rolling, Hepburn returned to sunny California, and, as it always did, the lovely autumn made way for the cold winter nip that moved eastward from the Catskill Mountains.

New York grasped at the last moments of vibrancy with bells jingling and the Rockettes jollily kicking in unison at Radio City Music Hall. But holiday fanfare did little to ease Toole’s daily commute. Every day he passed the same stores, the same delis, traveled through the same dark tunnels of the subway—a commute that was more than an hour long with two subway transfers. He coursed back and forth through the subterranean bowels of Manhattan, professor in the morning and student in the afternoon, only to discover that after tuition, rent, and food he barely had any money left over. The ominous blue haze he saw from his twelfth-floor office in mid-October descended, and he saw the city as “its usual busy, preoccupied, hustling self.”

With the weight of his spring semester shifted to teaching, it made sense for him to move closer to Hunter. He found a fourth-floor apartment and roomed with fellow Tulane alumnus Kent Taliaferro at 128 East 70th Street—a slender, red brick house on a quiet side street, shaded by an overarching canopy of trees. Ironically, while Toole struggled for financial viability, he now lived in the Upper East Side, one of the most affluent sections of Manhattan. Granted, the block of 70th Street he lived on was originally built in the 1870s for stables and stable hands. The relatively modest homes, for Upper East Side standards, created a quaint feel to the block. At the corner of Lexington and East 70th Street, the neon sign of Neil’s Coffee Shop glowed, even in the blurry white of the winter snow, welcoming students and professors, a place where Toole could get a hot cup of coffee before walking a block to Hunter.

Toole spent Christmas and New Year’s Eve that year in New Orleans and Lafayette, enjoying the calm pace and mild weather of Louisiana. Fortified with home-cooked meals, he returned to blustery Manhattan. At first the novelty of snow brought him some enjoyment. He went sledding with friends in Central Park, where they climbed the hill of the pilgrim statue near the entrance at 72nd Street, and they could see the three towers atop the Beresford—an upscale apartment building on the Upper West Side, which hovers like a dreamy castle keeping watch over the urban forest. During this playful winter day, Toole plopped into a mound of snow. A companion snapped a photo: the New Orleanian sits in his frigid New York throne.

But his proud smile withered as he returned to his routine during days that seemed successively colder and snowier. He walked to class against the frigid winds that whipped between the buildings—that burning winter air that creeps into one’s bones. The New York Times declared the snowfalls in January and February of 1961 created “the worst winter in 80 years.” Toole observed that New Yorkers developed a “snowbound mentality.” Bundled under layers of clothing, he saw the millions of faces walking the streets and casting their gaze downward to avoid the chilly blast. For a man accustomed to the subtropical climate of Louisiana, the winter of 1961 proved nearly insufferable. He wrote to Joel Fletcher, “In my present snowbound condition, I find that letter writing alleviates some of the drabness and discomfort of the below-zero temperature.” During this period of reflection, his track in New York started to mirror his previous experience. In the autumn he had absorbed and observed the character of the city, but winter bred bitterness, reflection, and questions of meaning and purpose. His New York endeavor grew tiresome. He confides to Fletcher, “As time passes, the tedium of graduate school magnifies; the Ph.D. looks like a nebulous and questionable reward for financial scrimping, stultifying research, and meaningless seminars.” When he had finished his teaching contract at SLI in the humid haze of the Louisiana summer, it seemed he had understood the purpose of his return to Columbia; but now, once again entrenched in the reality of life in Manhattan, it all lacked a clear point. Of course, his financial struggles colored his perception. Egos volleying across a graduate seminar table, displaying one’s own brilliance and seeking to gain the approval or even slight recognition from a professor, can seem pointless when compared to the weight of surviving in the city.

While Toole had come to New York for Columbia, now Hunter College took much more of his time and energy. By the spring semester he rarely spoke of Columbia in letters home. In March he writes, “I can only write about work, work, and work.” Being so close to his place of employment meant he could teach in the mornings and be available to substitute for night classes at Hunter. Of course, more classes meant more students. And after completing one full semester, he gained a far more complex picture of Hunter than his initial assessment in October. Like many teachers, he expressed mixed feelings about his students. He varied from excitement over their potential to a view no more flattering than his cartoons of the Newcomb College women at Tulane. But his vacillating reactions indicate his students held his interests more so than did his professors at Columbia. And, in turn, his students found him an engaging and refreshing teacher.

Ellen R. Friedman took only one class with him, but he she never forgot him. On the first day of class he walked into the room of all female students and issued a writing assignment. “Answer this question: What profession would you like to pursue and why?” He knew many of them wanted to be schoolteachers, the basis upon which the college was founded. Predicting cliché responses he stipulated, “And don’t tell me you want to be a teacher because you like children. That is not a sufficient reason.” Little did his students know, he was struggling with his own career path. Reflecting the same question he asked of himself, he pushed the students to think deliberately about their answers and their futures. “He turned on an intellectual light,” Friedman remembers. “He began a chain of thinking for me. . . . He was one of the first professors that actually made me think.” Years later, after reading Confederacy , it became clear to Friedman that there was another side of Toole she had not seen in class. She does not recall humor as central to his teaching. He was more caustic in his responses. “He had a way of letting you know that what you said was not that good or that you missed something.” Considering he was only a few years older than his students Toole had to walk a fine line; he had to maintain his professional stance and focus, never to be misinterpreted as a friend. Friedman recalls how young he looked, and yet he carried himself in the classroom with the ease of a confident professor. He dressed in a tweed jacket with a collared shirt and tie. Sitting on the edge of his desk, one foot propped up and the other dangling to the ground, he lectured with clarity. Inevitably, some of the students developed a crush on him.

Dear Ken,

I took my last exam today, followed it with a voice lesson “chaser,” and then found your letter waiting for me, as effective as a soma holiday.

I spent Tuesday reading, sunning myself, and playing a terrible game of tennis at Sebago Beach. I’m not sure whether its sunburn, windburn, or frostbite, but I did lose my “nightclub pallor.”

It has been suspiciously quiet around here. Today is Henry’s birthday and I’m sure that 42 relatives are going to pop out of closets when I’m not looking.

If you happen to receive a loaf of rye bread in the mail, don’t mistake it for a displaced “care” package—it would more likely be from my mother. She misses serving dinner to you, but not possibly as much as I miss being with you. I love you, I love you, I love you.

Ellen

p.s.: the package hasn’t arrived yet—I can hardly wait. My love to you darling—Ellen.

The author of this letter remains a mystery. It was not from his student Ellen Friedman at Hunter, nor would he normally invite one of his students to call him Ken. In fact, he usually reserved Ken for his friends in Louisiana. But this woman appears to live in New York, considering her visit to Sebago Beach. And Toole apparently charmed her mother and became familiar with her family. But who was Ellen? A fellow graduate student? A person he met at a bar? Perhaps an undergraduate at Columbia or Hunter? Whoever she was, she energetically bounces from school to vacation to her family and repeatedly declares her love for him. It seems he developed some affection for her, as well, after seeing her “night club pallor,” likely during an evening of dancing.

It has been said that Myrna Minkoff is a composite character of the Jewish students at Hunter. As Fletcher suggests, Toole looked to his Hunter students and “Myrna Minkoff, the unlikely heroine of Confederacy was under observation.” Thelma Toole understood that Myrna Minkoff was an actual student of his at Hunter. In fact, she worried a lawsuit would come out of publishing the novel with the actual name of the student. And Anthony Moore, who served with Toole later in the army and was in his company during the period that he wrote Confederacy , remembered that Myrna was “based off a girl that was infatuated with him in New York.” Moore felt it mean of Toole to mock a woman who loved him, as Ellen clearly did. Of course, there is no spirit of revolution in Ellen’s letter. It has no plots for social upheaval or unsolicited advice like the letters of Myrna Minkoff’s to Ignatius Reilly. But it does suggest that Toole had a relationship with a young lady in New York City. And if he used her for Myrna Minkoff, it would certainly illustrate his boundless satire.

As a professor, Toole clearly earned the respect of both the students and the administration. His supervisor, John Wieler, filed a “highly favorable” report on his teaching. And in the spring semester they awarded him a literature course, a rare honor for a part-time faculty member without a PhD. As he admitted to Fletcher, “The Hunter hierarchy has been more than kind toward me.” At least for one course he could delve into what he loved. In a letter to his parents he refers to this course as the Stein class, likely referencing Gertrude Stein, either in the character of the students or the content of the course. “Classes are all proceeding perfectly, The Stein Class, after a little slapping about the head and shoulders has developed into one of the most interested, alert of the four classes.” In general, students enjoyed his classes, or so he tells his parents when he reports evidence of his virtuosity as a teacher:

The professor whose classes I assumed in night school last week phoned me this afternoon to ask, “what did you do to those classes? They said they were the most exciting classes they’d ever had, covering psychology, philosophy, history and literature. All the classes want you back. They spent all the time telling me how thorough and fascinating you were.” (One of the classes applauded when I finished one night!) So there’s some recompense—aside from the financial—for all this fatigue.

As Patricia Rickels often said of Toole, “Always on stage.... He was always on stage.” Wieler praised him, and his students adored him. But like any teacher he had moments of frustration. Ellen Friedman sensed that Toole was “a little baffled by New York girls. We were a bit more independent, not Southern belles.” Dalferes remembers some moments where he felt he could not get through to them:

He used to get very annoyed with the stupidity of Hunter. He felt the students were only interested in anti-Semitism. He wanted to bring the glory of literature to people. If people couldn’t recognize that he would get depressed.

It is no surprise a young, bright professor, one who had a remarkable writing talent in his first year of college at the age of sixteen, would lament a crop of freshman or sophomore papers. But Toole had not forgotten where he had taught the previous year, which offered him some perspective on the skill level of the Hunter students. Nick Polites notes that Toole “acknowledged they were a lot more sophisticated and brighter than the students in Lafayette.” And if he was unimpressed by their writing or preoccupation with politics he at least found some pleasure in observing them. At first he found in the students an amusing strain of reckless rebellion. He admits to Fletcher, “I like Hunter—principally because the aggressive, pseudo-intellectual, ‘liberal’ girl students are continuously amusing.” Like many college students, their rebellion was often enacted under vague and half-formed notions of the world. While students picketed for everything from academic freedom to the cost of tuition, they also fought against oppressive traditions like the onerous yearbook dedication page. In the 1961 Wistarion the staff dedicated the yearbook to “friendship,” declaring, “This is the year we are free from such shackles” of dedicating the book to a person. It was this kind of absurd rebellion that Toole found amusing and silly.

The influence of Judaism at Hunter and New York also intrigued and at times unsettled him. In the drafts of his poem “New York: Three Aspects,” he sketched three Stars of David and compared the entire city to a mixed metaphor of both a biblical ark and a bank. And many students were declaratory about their Jewish heritage. They had a robust Jewish identity the likes of which Toole had not faced in Louisiana. Their intense sensitivities toward anti-Semitism blended with their aggressive political statements tried his patience at times. Polites remembers, “[When] Ken spoke of his students at Hunter . . . I recall a somewhat derogatory note in his voice. Maybe it was that he thought them ‘pushy.’” Toole, in his own way, pushed back. Emilie Griffin remembers visiting one of his courses in May of 1961 when he wrote on the board, “Anti-Catholicism is the anti-Semitism of the liberal.” It was a line she would quote back to him years later in a letter, having never forgotten the provocativeness of the statement. Griffin identified Toole as a liberal, but she is quick to point out that the liberal way of thinking in New York City troubled Toole. He felt that New York liberals quickly cast a Southerner as a racist and a Catholic as a papist. As he saw it, while they railed against bigotry, they failed to understand their own prejudice.

In Louisiana Toole avoided declaring a particular political persuasion, preferring to observe and satirize people. But the North seemed to thrust him into political commentary. When it came to the South and the escalating social upheaval in the Southern states, combined with the brash comments he encountered in Manhattan, he could barely hold his tongue. Dalferes tells of one occasion when they went to see Birth of a Nation at the New Yorker Theatre. During intermission they overheard a conversation between a man and a woman. The woman remarked, “The movies take a grain of truth and blow it out of proportion.” The man replied sarcastically, “What truth is there in the South?” Unable to restrain himself, Toole interrupted the conversation and began a passionate tirade in the likes of Bobby Byrne. “During Reconstruction,” he bellowed as he began his sermon, recounting the injustices dealt to Southerners at the hands of the Yankee carpetbaggers and the policies of the federal government aimed at punishing the Southern states. Dalferes was as surprised with his eruption as the man and woman were. But she recognized, “It took guts to do that in New York at the time.” She eventually determined, “In New Orleans he was a liberal—but not in the North. He was Southern to the core.”

For as much as New York grated his social and political sensibilities, it also provided him opportunities to see artists he would not otherwise witness. It was one of the reasons he originally fell in love with New York. He had access to forms of entertainment available nowhere else in the United States at the time. And aside from the obvious Broadway productions, Toole loved a good concert. In New York he saw one of his favorite singers, Frances Faye. As Polites recalls,

He was a great admirer [of Frances Faye], and his admiration was infective.... He had seen her in performance at a nightclub during his New York days. He had all kinds of stories about her, how she fell off a stage during one performance and broke a leg, which he thought hilarious.

Her banter drew audiences, especially Toole, to her shows as much as her singing did. She was quick witted, an absolute parody of gender roles, and confident beyond measure. While no scarlet beauty or nightingale, she was a masterful satirist. At a time when sexuality and gender remained a cloaked and closeted conversation, she held a mirror up to society and made them all laugh at the reflection of the sexual complexities around them. In one of her most famous songs, “Frances and Her Friends,” she strings rhyming names together, twisting gender roles, and turning relationships into a string of lovers: “I know a guy named Joey / Joey goes with Moey / Moey goes with Jamie / And Jamie goes with Sadie. . . . ” This could go on in limitless variations, each verse ending with, “What a drag, what a drag / I’m not mad / I’m too hip to get mad.” In the gay community, Faye has been celebrated as a pioneer for her openness. But her audacity and fearlessness on stage attracted both gay and straight listeners. As the Washington Post reported of her concert on February 18, 1961, “Frances Faye hit the New York scene with the impact of a 10-ton truck smashing through a concrete wall.” Her shows were nonstop adrenaline-infused jazz sessions. She cranked out riffs on the piano, bellowed her lyrics, playfully changing lines here and there, adding jokes as she went along. It was precisely the kind of humor Toole loved—fast, witty, and unpredictable. And yet critics observed she achieved a balance of intensity and intimacy. Variety reports of her March concert in 1961, “She makes the big 750-seater an intimate room, turning the stint into one big house party.” Having started performing on stage when she was fifteen, she knew how to hold masterful control over her audience.

Much like Faye, Toole fostered his talents of quick wit, interpretation, and satire at an early age. He was attracted to this artist that projected her style: bold, raw, and unrefined. Polites observes, “It wasn’t necessarily the voice [he] admired, it was the style.” In other words, it wasn’t the aesthetic of what she created, as much as how she created it. So impressed with her, Toole once wondered aloud to Fletcher, “Is Frances Faye God?” As Toole lifted Faye on high as a deity of artistic creation, he reflected on his dream of becoming an artist who, like Faye, would burst onto the New York scene.

He began drafting “sketches” of a character he named Humphrey Wildblood, who would eventually become Ignatius Reilly. He left no detail of these sketches, although from what friends remember of his stories, they were likely short narratives, quick comical vignettes, a method of creation similar to his comics at Tulane. Since the earliest reference Toole makes to working on the book is described as “sketches,” it is no surprise that Confederacy is a picaresque, a series of episodes, akin to the method of storytelling he preferred. Here were the beginnings of Ignatius, drafted in New York City, the place to which he would send Ignatius at the end of the novel, exiling him from New Orleans.

Unfortunately, all that remains of these “sketches” is the name Humphrey Wildblood, mentioned in a letter. Were the sketches set in New Orleans? Were they set in New York? What did Humphrey Wildblood look like? Nobody seems to know. Perhaps they were sketches only in his mind, narratives crafted from observations and drafted in his imagination to pass the time on the subway between Columbia and Hunter. Whatever the case, his movement away from academics and toward a creative endeavor in the early months of 1961 mirrors the winter season of 1959 when he wrote “The Arbiter,” critiquing the role of the scholar-critic through poetry. In the winter of his discontent he makes his turn toward becoming a novelist. And New York, the epicenter of publishing, was an appropriate place to do it.

While he had yet to compose something he considered worthy of publication, he now entertained the life of a writer more seriously than the life of a scholar. And perhaps an attraction to the “literary life” in New York offered him some incentive. Along these lines, Polites recalls Toole telling him that he had become friends with the novelist James Purdy in New York. Purdy’s novel, Malcolm, had been published in 1959 to international acclaim. And Polites remembers Toole being “impressed knowing a published writer.” But Toole also “talked about how strange, almost weird, Purdy seemed to be.”

In 1960 Purdy moved to New York, so their encounter was possible. And Purdy could certainly speak to Toole about the struggle to find one’s own voice as a writer and the challenges of getting published. He had worked for years as an aspiring novelist until he sent his privately printed short story collection to poet Dame Edith Sitwell who jump-started his literary career. Undoubtedly, Toole could have learned a great deal from Purdy. But if they had been acquaintances, there is no record of it in the Toole Papers. And he never mentioned Purdy to Fletcher or Rickels. Like his supposed offer from Yul Brynner that he once bragged about to his friend Cary Laird, Toole may have been trying to impress Polites, which he often tried to do. Whatever the case, the story suggests that Toole wanted to see himself in the literary circles of New York. How he saw himself fitting into that scene, if at all, is unclear. He was far too straight-laced for the Beats. Purdy may have been a bit too offbeat for him. One thing became clear, though; he did not see himself traveling the long road to the PhD.

Perhaps that was just as well. As Toole questioned the point of his academic pursuits, the army called his number. With growing tensions in Berlin and Vietnam, Toole could no longer defer the draft. In June he packed his belongings in his apartment. The neighborhood that gave way to the raucous Cold War scenes nine months earlier, offered little excitement as he prepared his departure. Dalferes came to his apartment to see him off. To save money, he told Dalferes, he had sent his belongings on a bus and then would take a flight to New Orleans. He despised long rides on buses. Dalferes and Toole parted ways in Manhattan, and he quietly left the bustling metropolis behind.

Some people say that New York has a way of breaking people. The friends closest to Toole sensed that he saw the city as much of a convoluted cultural mélange as his own hometown. But Dalferes noticed he seemed restrained in Manhattan. She knew that he, “Loved to party. But he couldn’t do that in New York. He was more formal.” Ultimately, she resolved, “He didn’t feel comfortable there,” largely in part due to the cultural abrasiveness he found in the north. While Pat Rickels claims he wanted nothing more than to return to Columbia, Dalferes claims, “He preferred New Orleans. He just wanted the prestige of Columbia.” Perhaps Polites got it right when he concluded, “While New York obviously meant a lot to Ken, I suspect he may have had something of an ambivalent relationship with the city.” In that regard, it paralleled his relationship with New Orleans. From far away, the city glows in myth and memory. Distance reinvigorates the spirit of the place. But once returned, the reality of the city rarely achieves those expectations.

Since his undergraduate days, Toole had pondered the role of the writer in society. But critiquing a story or a poem is quite different from actually writing one. Therein lay the rub. As a master of mimicry with exceptional control over written and spoken language, he still struggled with the development of a narrative sustained over the course of hundreds of pages. When Emilie Dietrich returned to New Orleans for a visit, they spoke about writing. They exchanged some ideas as they tried to crack the code of composition, sharing in their ultimate dream of becoming fiction writers. After her return to New York, she wrote Toole excitedly, confessing that she had begun a promising writing project. In her letter she offers Toole advice, perhaps alluding to their previous conversations about the writing process. “I think it must be just that you have to be saying something that you really mean . . . not just dredging characters and situations up because they are charming.” She strikes at the heart of his struggles as an aspiring fiction writer. He had a knack to quickly identify the absurd and to mimic it. But how does one bring it all together to form a cohesive story with true meaning? This question would hound Toole for years.