Butterfly in the Typewriter

Toole loved his city, and he undoubtedly loved his parents. But having held a teaching position at two colleges and earning a series of promotions and commendations in the army, he aspired to something more than a small apartment with two aging parents as roommates. He must have had some inclination that such a living condition would be difficult, although he may have underestimated the stress of it. Whatever the challenges, he could take solace in his master plan. So, like Theseus entering the Labyrinth, Toole held his novel as the string to lead him out of the maze that New Orleans and life at home would inevitably become.

In the year ahead he would use his spare time to refine his manuscript for submission to publishers. And in that year his mother, overjoyed to have him back home, encouraged his pursuit. She recalled the day he returned and presented her his manuscript. She read the first chapter and told him it was “promising.” The next day she completed reading the whole thing. “It’s a masterpiece, son,” she told him. She was excited at the prospect of her son’s work, but she noticed something different about him. He seemed quieter, as if completely absorbed by his book. She would eventually find his restraint and retreat worrisome, but for now he was to begin his teaching job, and the Toole household would enjoy a boon to its anemic coffers.

A few days after his return home, Toole visited Bobby Byrne. The two former officemates chatted over coffee. Never mentioning the novel, Toole told Byrne about his new job at Dominican. As a staunch devotee to the Franciscan order, Byrne was horrified. He found the Dominicans ridiculous and potentially dangerous. He cautioned Toole that “that Byzantine institution” would surely ruin him. Toole likely dismissed the comment with his trademark half smile. What an Ignatian thing to say. Despite Byrne’s ill feelings toward the Dominicans, Toole had his plan that would ensure a short tenure at the college. And he retained his optimism as he began the school year.

The quaint college, a few blocks from Tulane and Loyola universities, offered him a warm welcome. While it did not hold the stature of its larger academic neighbors, the small school had a charming campus and rich traditions. Two towering palm trees marked the entryway to campus along St. Charles Avenue, and a brick pathway led to the main hall; a three-story building adorned with a cupola, onion-shaped dormers and a two-level arcade shading the huge sash windows. Toole taught in a classroom on the second floor. And among the faculty composed primarily of clergy, he quickly gained the adoration of his colleagues and students. The students were thrilled to have a smart, young scholar—who was also a New Orleanian—from the Ivy League teaching them. He left an impression of intelligence and gentility. In 1980 the Dominican alumni newsletter described him as

The gentlemanly English teacher who asked for [student’s] permission before removing his jacket on humid summer days in Dominican’s fan cooled classrooms.... Students will remember his polite Southern manners, his impeccably neat appearance, his dry humor, his insight into literature and his profound understanding of the absurdities of life in the 1960s.

Of course, his students at the time were unaware of his novel writing. He kept his two roles as teacher and writer separate. And while he would later comment to his friends about the drudgery of teaching, once he was in the classroom it appeared to his students that he enjoyed it, and they enjoyed him. Perhaps his most lasting devotees to his memory at Dominican are the three Trader sisters. As they recalled, Toole routinely entered class at the last moment. And at times he could take on that supercilious tone so evident in Ignatius Reilly (as well as Toole’s mother) that could be entertaining. He “ridiculed Reader’s Digest” and occasionally spoke of “legitimate theater.” He often commented on “the coming trend of making books into movies.”

He enjoyed the praise and attention at Dominican, but much like Hunter College, the job was a means to an end. And while most people had no idea he had written a novel, there were a few people that he trusted. In his first semester at Dominican, a senior named Candace de Russy caught his eye. And his mother, concerned about her son’s introverted behavior, encouraged him to invite friends to their home. Whether by chance or design, Toole and de Russy kept running into each other on campus, although it seemed to her that the young professor sought her out. Over lunch or coffee they would talk about literature. He was undeniably smart, but de Russy thought he “projected a kind of loneliness, even timidity,” even though he was always “proper and appropriate.” As their conversations became more frequent de Russy noticed there was a “remoteness” about him, as if he had difficulty sustaining a conversation. He would listen, and he could tell a great story, but engaging in an exchange of ideas became awkward and clumsy for him. For a moment, she thought he might be depressed.

One autumn afternoon Toole invited her back to his house to meet his parents. They strolled down St. Charles Avenue to Audubon Street. Thelma Toole greeted de Russy at the door and eagerly welcomed her into their home. She was introduced to his father, as he sat in a darkened room. He kindly waved but did not join them for tea. Over the course of the afternoon, it seemed to de Russy that Thelma was careful to create a pleasurable experience. It occurred to her that her invitation might have stemmed from Toole’s interests in dating her or from a mother’s hope for her son “to gain a more normal life.” It must have taken substantial trust on Toole’s part for him to invite home a student at the college where he taught. But de Russy, perhaps through her empathy for him, had gained his confidence, so much so that he talked to her about his novel.

What she previously identified as depression, she now recognized as an astoundingly deep immersion in his manuscript. She noticed that Toole acted as if his mind was split between reality and his book, not as if he couldn’t distinguish between the two, but because he had poured his soul into the novel. “The center of his existence had become his book,” she observed. “When he walked on campus, he looked straight forward, not making eye contact, and every once in a while he would kind of chuckle to himself as if something just struck him as absurd.” He discussed characters and scenes with de Russy, but sensing that more lay underneath his plot summaries, she attempted to draw out what troubled him. She gleaned from their conversations that he had “a consuming desire to have the book acknowledged and recognized. He was not egotistical, but it was something deeper. He believed in the exceptionalism of the book, but he had anxiety about it. It had very much to do with his identity and profound sense of self.”

So Toole continued editing for a few months after his return, until a guillotine that had been rising, slowly and silently for months, finally dropped. Back when Toole was settling into his home, editing his novel, and drinking coffee with Bobby Byrne, another man who was about to make the history books walked about the Crescent City. Another New Orleanian, Lee Harvey Oswald, was living in Uptown in the summer of 1963, two miles away from the Toole home. Oswald spent his days organizing a New Orleans chapter of the Fair Play for Cuba Committee and passing out pro-Castro propaganda along Canal Street. By November of 1963, Oswald had moved to Dallas, Texas, where he worked at the public school book depository. And on a sunny day in Dallas, as John F. Kennedy’s motorcade slowly rolled down the street with the president and First Lady waving to crowds from the back seat of a convertible, two bullets ripped through the president’s skull. Oswald was charged with the assassination. Three days later, as he was transported to the county jail, nightclub owner Jack Ruby sent a bullet of his own into Oswald’s abdomen. The shots echoed throughout the country. America stood paralyzed, just before hurling itself into the most turbulent decade of the twentieth century. And as Toole watched this tragedy unfold from his home in New Orleans, his months of editing and rewriting came to a halt. His fingers rested still on the keys of his Olivetti-Underwood typewriter, and all was silent. He later confessed, “The book went along until President Kennedy’s assassination. Then I couldn’t write anything more. Nothing seemed funny to me.”

By the beginning of 1964, Toole decided to submit his novel to a publisher. While most writers and agents would have sent a manuscript to several publishers, he selected one: Simon and Schuster. It was a house undergoing a transformation, in large part due to its star editor Robert Gottlieb. While Simon and Schuster had once focused on nonfiction and self-help books, Gottlieb ushered in fiction titles such as Catch-22 and the novels of Bruce Jay Friedman. Toole had an especially “intense personal reaction” to Friedman’s Stern. And when his mother later asked why he submitted the manuscript to only one publisher, Toole explained that Simon and Schuster was reputable and prestigious. He deemed that their books sold, while others collected dust on bookstore shelves. Toole wanted more than publication; he had an intense yearning to reach as many readers as possible.

Today, most large publishing houses acquire works through literary agents. But in the early 1960s Simon and Schuster not only accepted unsolicited manuscripts, it also meticulously documented submissions, considered the work, and then responded to authors. So the novel that carried the weight of Toole’s future traveled from the small apartment in New Orleans to New York, and it landed on the desk of Robert Gottlieb. In many ways, Toole could not have been more fortunate. Michael Korda, an editor under Gottlieb who eventually rose to editor-in-chief at Simon and Schuster, recalled Gottlieb’s fierce dedication to the art of literature. In Another Life Korda explains that Gottlieb approached his role as an editor like a midwife in the creative process—he could see both the big picture of the book and “how intricate changes might bring out the best in it.” And he was surpassingly industrious. He labored for years over Catch-22 with Joseph Heller. Even as the advent of the literary agent emerged among trade presses, he avoided schmoozing at martini-filled business lunches in midtown Manhattan restaurants, preferring that anyone interested in having lunch with him bring a sandwich to his office. In fact, the first time Bruce Jay Friedman arrived at Simon and Schuster to have a working lunch with Gottlieb, he was surprised to find the rising star of Midtown offering him a plate of raw vegetables to munch on while they went over the manuscript for Stern. And of the voluminous number of manuscripts that flooded Simon and Schuster every week, piling up on Gottlieb’s desk, a new humorous writer from New Orleans stood apart from the rest. Gottlieb’s assistant, Jean Ann Jollett, loved Toole’s manuscript and recommended it to Gottlieb. After he read it, Gottlieb wrote encouragingly to Toole.

In just over a year, Toole had gone from staring at a blank sheet of paper in a borrowed typewriter in Puerto Rico to catching the interests of the most dynamic editor in New York. Things were proceeding according to his plan. Next, editor and writer had to figure out their delicate dance. As Gottlieb knew, every writer is different, and Toole had no experience in publishing a book. Toole had been praised for his writing abilities all his life. When he was sixteen his college professor said he was ready to submit to an academic journal. And his professors at Columbia had little to critique about his writing. But New York publishers did not operate in the realm of grades or degrees. Toole was entering a world of both art and business, subject to market forces, although not driven by that measure alone. However noble the pursuit of publishing literature, at the end of the day it is a business. His novel not only had to be good, it had to sell.

In June of 1964 Toole made arrangements to go to New York and visit with Gottlieb, so author and editor could work together, presumably to address some issues in the manuscript. But Toole could make it only near the end of June when Gottlieb would be in Europe. It was the first misstep in this dance that would become increasingly awkward. Jollett wrote to Toole to warn him of the situation, hoping that he could make his trip earlier in order to meet with Gottlieb. She ended that letter asking Toole, “Is now the time for me to tell you that I laughed, chortled, collapsed my way through Confederacy? I did.”

Unfortunately, Toole and Gottlieb could not coordinate their schedules, so Gottlieb sent some of his editorial comments in a letter. His critique was direct. He took issue with Toole’s plot structure, particularly at the end of the novel. He admitted that Toole had created brilliant scenes and “wittily tied them together at the end.” But the “threads must be strong and meaningful all the way through.” His comments echoed Emilie Dietrich Griffin’s advice when she wrote to Toole in 1961 saying, “You have to be saying something that you really mean . . . not just dredging characters and situations up because they are charming.” Gottlieb reiterates, “There must be a point to everything you have in the book, a real point, not just amusingness forced to figure itself out.” After his criticism, he encourages Toole to keep working on the book, while suggesting some time away from the manuscript might be helpful. But he clearly states, “Please, no matter what, let me see the book again when you have worked on it again.”

While in New York, Toole visited Joe Hines, an English instructor he had met in Puerto Rico who lived on the West Side of Manhattan. They spoke of Toole’s venture into publishing that was now in limbo. Once Toole returned to New Orleans, Hines wrote to him,

Dear John,

It has now been some time since you returned to the land of the night-blooming jasmine. I wonder how your meisterwork is progressing. Have you finished and presented it for re-examination to Miss Jollett? I take a rather selfish interest in the book, since, upon its completion and publication, I will have some contact, however slight, with fame and notoriety; one needs a touch of megalomania to get by.

Hines spends the rest of the letter discussing a trip to New Orleans to visit Toole, who had told him of the “interesting and unusual” city. Later that summer, Hines had the benefit of having Toole as his New Orleans tour guide. During the visit, they took in the film Becket, the story of the thirteenth-century Saint Thomas à Becket, which left Toole questioning the reasons behind the saint’s “sudden conversion to goodness, religion, selflessness.” At a time when Toole was urged to think most deliberately about the reasons for his characters and their behaviors, he found the about-face of a famous religious figure puzzling. While the audience liked to see characters transform, rarely do people change so drastically. Toole posed the question to Hines, who responded that it must have been “the grace of God,” a response that Toole likely found unhelpful. Hines provided Toole a break from edits and rewrites, allowing time to talk to a friend and showcase his city.

In many ways New Orleans still gave Toole a sense of wonder as he spoke with his army friend and showed him around. After nearly a year back at home, preparing the revised manuscript to send back to Gottlieb for review, he still relished the quirkiness of his hometown. One evening in the summer of 1964 he met with Byrne and Fletcher at the Napoleon House. Fletcher had recently returned from Europe and like any globetrotter back in his provincial home, Fletcher was eager to share with his friends stories of his adventures. But he was “disappointed to discover that all they seemed to want to do was gossip about their uptown New Orleans neighborhood.” Toole was deeply invested in his city at the time, rewriting a novel about the people of New Orleans, the very people Byrne and he discussed. Let alone, Ignatius Reilly had nearly consumed his mind for well over a year, and here sat across the table one of the major inspirations of that character. Fletcher felt snubbed by his friends, but it must have been a productive evening for Toole.

In the fall of 1964, as Toole started his second year of teaching at Dominican, he sent the revised manuscript to Gottlieb and awaited his response. Still troubled by some parts of it, Gottlieb asked his close friend and literary agent Candida Donadio to read it. While Gottlieb was not trying to impose an agent on Toole, he knew that if he were to get an agent, Donadio, who represented Joseph Heller and Bruce Jay Friedman, would be the one for him. Both agent and editor agreed on some significant changes that needed to be made to Confederacy. In mid-December Gottlieb writes to Toole, summarizing their suggestions. They agreed Toole was “wildly funny, funnier than anyone around, and our kind of funny.” They praised almost every character in the story with the exception of Myrna Minkoff and the Levys. They concurred, “Ignatius is in trouble.” With directness, Gottlieb critiqued the character Toole had been developing for years, “He is not as good as you think he is. There is much too much of him.” Donadio and Gottlieb also agreed the book was too long. But the area that they found most disconcerting was its lack of “meaning.” Gottlieb writes, “With all its wonderfulness . . . the book does not have a reason . . . it is a wonderful exercise in invention, but . . . it isn’t really about anything.” Gottlieb seems at a loss as to how to direct Toole, at least through the medium of a letter. But, yet, he restates his dedication to him, claiming, “We can’t abandon it or you (I will never abandon Mr. Micawber).” While Gottlieb admits that the book could be “improved upon,” he also says it would never sell. He continues on a rather confusing explanation, “When Candida and I know something is basically for us, but not right, it is very difficult to have it right for other people in town on our wavelength; and the others are out of the question.” So what was Toole to do? He could try another publishing house, but Gottlieb, who had already dedicated much time to the novel, told him it needed a particular kind of editor. And Gottlieb was right. Publishing houses were not clamoring to release comic novels in the mid-1960s. They have always been difficult to place, but Gottlieb had edited some of the best in American fiction. From Toole’s perspective, this letter must have been difficult to swallow, as well as somewhat disorienting. Where did he stand in the midst of these messages? Gottlieb tells him that he could give up on the book but then tells him that is not a good idea. And yet the book was not really marketable; however, Toole shouldn’t despair. The letter fluctuates with Gottlieb’s stream of thoughts. And in the end it reads more like a personal letter than business correspondence. Having typed it himself, Gottlieb confessed he could not “dictate this kind of letter,” a letter from an editor searching for a balance between honesty and encouragement to help a young writer.

That same month, Toole received a letter from his friend Joe Hines. Having spent some time with Toole in New Orleans, Hines now addressed him as Kenny, instead of John. He discusses the works of Evelyn Waugh, Toole’s favorite writer, and then asks about the status of the book, the project that dominated Toole’s life:

One wonders how your masterwork is doing. When last I saw you, you expected to have the revision completed before the beginning of this semester and sent winging on its way to Jean [Jollett] so that she might laugh and chortle on every reading of each page. I wonder if it has been sent to “your publisher” and when it may see the light of day and the book store’s shelf.

But something seems to have changed for Toole over the holiday season. In late December of 1964, Toole retreated to Lafayette and met with his friend J. C. Broussard. Broussard saw a man drastically altered from the inflated ego he witnessed in the Sazerac Bar two years prior. Reporting the sad episode to Fletcher, Broussard writes,

Ken came for two days at Christmas and, under the influence, confided in me his deplorable state—a virtual incarceration (entre nous) with parents prematurely senile and giving full vent to a latent possessiveness. My advice to him, who is too young for such, was to escape after this year. One can tolerate the aged when they are really old and when the disparity in the age of parents and children is not so great.

Over the course of the evening, Toole did not discuss his correspondence with Gottlieb. He must have labored over the words of the man who held the key to his escape from his current situation, but instead with his guard down after a few drinks he spoke to Broussard about his parents. It is possible that the words of his mother lay heavy on his mind as well. According to Nick Polites, Gottlieb’s fluctuations between praise and critique drove Toole’s mother wild. During this period, Polites remembers making several visits to the Toole house, where he sat in audience to her rants. He recalls,

Whenever I visited, Ken’s mother would sit with us, and Ken would tell me of another letter from the publisher requesting more changes, and Ken’s mother would take over and rail in the most sweeping terms of “art” and “beauty” and “genius” and how publishers didn’t understand anything at all. And Ken would sit silent as his mother would swell with scorn. It was quite a performance.

From such testimony, one wonders whose work Gottlieb had criticized. Surely the editor discussed the novel, but by extension of the mother-son relationship, in criticizing her son’s genius, he berated her, as well. Thelma may have believed her tirades in the parlor defended her son’s honor. She likely detected that Gottlieb’s words fell hard on him, but her theatrics may have exacerbated the issue. Had Toole been receiving these letters away from home, in his own apartment, he may have been spared the protective tirades of his mother. Then again, he may have felt even more detached and lonesome if he had not had Thelma to share in his disappointment. And one can only imagine if Thelma performed with such vehemence in front of a guest, how she would have carried on when they were alone. Byrne sensed this startling disconnect between Thelma’s public praise of her son and their one-on-one interactions. In the 1995 interview with Carmine Palumbo, Byrne recounts how his aunt, who taught Toole in grade school, used to talk about Thelma bragging about her genius son. When Byrne told Toole of this, he looked puzzled, saying, “My mother spends all her time telling me how stupid I am.” Toole received sharp criticism from both Gottlieb and his mother, as he struggled to determine how to edit his novel. And from what Polites witnessed, Thelma amplified Gottlieb’s criticism, stirring a toxic mix. Some part of Toole must have wanted it all to end.

Toole decided to request Gottlieb return the manuscript. He was almost ready to give up. In January of 1965 he writes to Gottlieb, “The only sensible thing to do, it seems to me, is to ask for the manuscript. Aside from some deletions, I don’t think I could really do much to the book now—and, of course, even with revisions you might not be satisfied. I can’t even think of much I could do to the book.” Clearly, Toole was demoralized. And a worsening situation at home did not help matters. Yet, he had come too far in a remarkably short time just to walk away from it. His mother, who never settled for retreat, would not approve of him giving up. And perhaps Toole recognized that if he gave up on the book, any hope of changing his situation at home was impossible. Toole couldn’t hold his “stiff upper lip” for long. Without an appointment or a call announcing his intentions, Toole went to New York to speak to Gottlieb face to face.

His mind must have reeled during the long trip north. He had restrained himself in his replies, trying to maintain his composure. What would he say when he stood in front of the man who had called his work “meaningless”? But when he arrived at Simon and Schuster, he found Gottlieb was once again out of town. For the second time, he stood in the office of his would-be publisher after a full day’s travel, only to find Gottlieb away. As he spoke to Miss Jollett, a tide of emotion overwhelmed him. As he later explained, he was “bent with obsequiousness” as he “almost sank through the floor in between . . . silences, cryptic comments and occasional mindless (for it had left me) absurdities.” Then he blacked out. Moments later, returning to consciousness, he left a request for Gottlieb to call him, and he returned to New Orleans. He had suffered a nervous breakdown in the offices of Simon and Schuster.

Toole knew he had embarrassed himself. To Gottlieb in 1965, Toole was one of the hundreds of talented young writers with manuscripts that would pass by his desk in any given month. And the busy editor could carry on a conversation through letters without it intruding on his daily work. But now Toole had come to his place of business unannounced and created a disturbing scene. As a potential partner in an artistic endeavor, Toole had presented troubling, unstable behavior. The whole fiasco even took Toole by surprise. What had caused him to act so irrationally? What compelled him to lash out at the one person he had identified as his lifeline? It was the first incident indicating the paranoia and the despair that would consume him.

After such an episode, many editors would have justifiably walked away, cutting off all communication. But in late February or early March Gottlieb called, and Toole asked him to clarify some of his statements made in the December letter. During that conversation, Gottlieb made the suggestion that it might be time for Toole to work on another novel, which Toole interpreted as “an opening to withdraw with at least a little grace.” By this point, Gottlieb knew he was dealing with an incredibly sensitive, possibly disturbed writer, and he opened all possibilities to Toole. Perhaps a rejection letter would have made a clean break between editor and writer. But something about Toole kept Gottlieb’s interests. Perhaps recognizing Gottlieb’s willingness to overlook the episode in New York, Toole let his guard down. He wrote Gottlieb a letter detailing the story of his life and the story behind Confederacy. It was rare for Toole to be so open and candid about his personal affairs. He confesses, “I’ve been trying to think straight since speaking to you on the telephone, but confusion and depression have immobilized my mind. I have to come out of this though, or I’ll never do anything.” He also recognized that his own relationship to his work was withholding him. The intensity that he felt toward his novel, which de Russy noted in 1963, had increased. He writes to Gottlieb, “Whenever I attempt to talk in connection with Confederacy of Dunces I become anxious and inarticulate. I feel very paternal about the book; the feeling is actually androgynous because I feel as if I gave birth to it too.”

He goes on to address Gottlieb’s critique of the novel. He fully acknowledges, “I know that it has flaws, yet I am afraid that some stranger will bring them to my attention.” He admitted that the Levys were “the book’s worst flaw” and Myrna Minkoff may be “a debacle.” But he holds fast to Irene Reilly, Santa Battaglia, Patrolman Mancuso, and Burma Jones because “these people say something about New Orleans. They’re as real as individuals and also as representative of a group.” Clarifying his point, he states,

One night recently I watched again as Santa bumped around while Irene sat on a couch guffawing into a drink. And how many times have I seen Santa kissing her mother’s picture. Burma Jones is not a fantasy, and neither is Miss Trixie and her job, the Night of Joy Club, and so on.

Gottlieb had suggested the novel had no point. Here Toole explains, at the very least, the novel makes a statement about New Orleans, because it offers the real New Orleans. Toole understood that Gottlieb meant it needed more universal significance. But his “doubts [turned] into despair” when one of Gottlieb’s comments struck hard. Echoing the editorial criticism that haunted him most, Toole writes, “The book seemed to become about nothing.” Toole’s frustration seems rooted in his confusion over how to change the novel. He confesses he felt “somewhat like a bouncing ball,” never finding a clear path to gain Gottlieb’s approval. Still, he determines to continue on with the revisions, accepting some of the editorial suggestions:

This book is what I know, what I’ve seen and experienced. I can’t throw these people away. No one has ever done much insofar as writing about this milieu is concerned, I don’t think. Myrna and the Levys may only serve to hinder the book, especially in their being extraneous. If the Levys cause me such problems, they don’t belong.... What was very accurate in your commentary about the revision was your separating real and unreal characters.

In other words, I’m going to work on the book again. I haven’t even been able to look at the manuscript since I got it back, but since something like 50 percent of my soul is in the thing, I can’t let it rot without trying. And I don’t think I could write anything else until this is given at least another chance.

In fact, George Deaux—who taught at University of Southwestern Louisiana, formerly Southwestern Louisiana Institute, the year after Toole left, and who also worked with Robert Gottlieb throughout the 1960s when Simon and Schuster published his three novels—recalls a moment when Gottlieb appeared exhausted with a writer, perhaps after reading a confession like the one that Toole sent him. In passing, Deaux mentioned to Gottlieb that he enjoyed Fellini’s 8 1/2 in part because he “identified with the Mastroianni character.” Gottlieb’s response was “uncharacteristically irritable, almost angry. . . . He denounced Fellini for his neurotic self-pity and went on to rail against artists generally for their self-indulgence.” Deaux initially thought that the criticism was aimed at him, but he realized Gottlieb was too polite and too direct “to make gratuitous comments about my personality . . . through the vehicle of an Italian movie. I concluded that he must have had a bad day with a self-indulgent author other than me.”

Gottlieb took a few weeks to reply to Toole’s letter. He wrote a cordial response, thanking him for the personal history. It still rings with slight derision as Gottlieb attempts to describe why Toole has been unable to produce satisfactory revisions:

When someone like yourself is living off from the center of cultural-business activities, with only a thin lifeline to that center, through vague and solitary contacts, everything gets disproportionate, difficult to analyze, to give proper weight to.

It is like those odd people who turn up in New Zealand or Tanganyika or Finland, writing or painting masterpieces. They have their own power, but they read or look as if the artist has had to discover the forms for himself. They don’t have the assurance of worldliness and mutual interest and energy with others. So I can see that to you I (or Jean) is not merely a person, but a voice with more authority than it could possibly deserve. Not that I’m not good at my job, because I am and no one is better; but that I’m just someone, and a good deal less talented than you.

Much has been made of this passage as an indication of Gottlieb’s Manhattan condescension. And while there is some value in that interpretation, it also stands true that Gottlieb refers to himself when he writes “the thin lifeline.” Whatever he thought about an artist rooted to New Orleans, his main point is true to an editorial philosophy that he had long held and expressed forty years later in an interview with Charlie Rose when he states, “I think the cult of editing is far overblown.” Gottlieb seems to suggest that Toole might be trying too hard to please his editor, instead of receiving the comments and figuring out how to apply them to benefit the novel.

In closing the letter, Gottlieb leaves the door wide open for Toole:

You are a good writer and a serious person and are doing your job seriously and modestly and of course it isn’t easy. . . . A writer’s decisions are his own, not his editor’s. If you know you have to continue with Ignatius, that is of course what you should do. I will read, reread, edit, perhaps publish, generally cope, until you are fed up with me.

Please write me short or long at any time, if only to say that you’re working (or not). Or if you like, show me bits of what you’ve done. Or don’t; whichever would be more useful. Cheer up. Work. We are overcoming.

Toole found Gottlieb’s letter “calming.” And he wrote back to him with renewed vigor for the novel. He reasoned that the decade between writing The Neon Bible and starting Confederacy he had pent up “unused energies” that “came flooding into this book and created too great a concentration of emotion.” But now he recognized that editing a manuscript so bound up in passion sometimes requires some bloodletting:

What is most apparent is the need for a red pencil through a lot of it. There are hints in the book of developing themes and ideas, but they seem to be abandoned before they become consistent statements. I see a possibility of having the book say something that will be real, that will develop out of the characters themselves and what I know of them, that will not simply be a superficial imposition of “purpose.” The book as it is evades certain logical consequences of the nature of the characters themselves, and in this way wastes a character or two. But I do have ideas for the book, and I am beginning to work on it. I hope that I’ll be able to send you a re-working of the thing in the not too distant future; since I am able to “see” and “hear” these characters, I can always work with them . . .

I have rallied, have begun to work. And spring is here.

As the academic year of 1965 came to a close, nearly completing his second year at Dominican, Toole reflected on his progress, although surely disappointed that his plan was not coming together as quickly as he originally thought it would. He writes a letter on May 4 to both Fletcher and Polites,

Since both of you know my writing project, I must say that eight air mail letters and one hour-long distance call from Simon and Schuster later, I am still faced with revisions. Although I am “wildly funny often, funnier than almost anyone else around,” the book is too “intelligent to be only a farce.” It must have “purpose and meaning.” However, it is full of “wonderfulnesses” and “excitements” and “glories.” But they worked “more than three years on Catch-22.” If and when it does appear, it will be unbearably “significant,” I imagine. Also, I am like “one of those geniuses who turn up in Tanganyika or New Zealand.” Poor New Orleans. Suppose I had sent the thing in from Breaux Bridge . . . or Parks. Broken and leering toothlessly, I may yet be on some book jacket. Looking at this more constructively, I have been (and am) fortunate in having the book reach so quickly people who have given me a degree of confidence in what I’m trying to do; goodness knows they’ve extended much time and interest.

Toole still maintained his sense of humor, and he certainly recognized his remarkable advances in his pursuit of publication. But getting a book published was clearly more difficult for him than being in graduate school or in the army. And for someone to whom success came relatively easy, this challenge took an emotional and psychological toll. It seems the revisions wore on his spirit to the point they began to change his outlook on life. Somehow, in his mind, what he calls his “pretentious rambling” connected to the Gulf Coast. He continues,

All of which leads to something else, I guess. The Gulf Coast looks better when you’re not there. I was there recently; it looked much more appealing in undergraduate days.

Fletcher always sensed that his friend would have liked to live the literary life in New York. Expressing such spite toward the city, and such disappointment in the surrounding region of New Orleans, suggests Toole’s possible routes of escape were becoming limited. The passages were narrowing, and he was losing grip on the thread that would lead him out. When his New York friend Clayelle Dalferes visited him in New Orleans, he told her he never had intentions to leave New Orleans again. “It was the only place he felt comfortable.” And yet, in that same conversation when she asked how his job at Dominican was going, he dryly replied, “Teaching smells.”

And as the city put itself back together, it seems Toole renewed his hope for publication. He sent a letter to Gottlieb in early January of 1966. The letter no longer exists, but from Gottlieb’s response, Toole wanted only to maintain connection with him. Nine months had passed since Toole’s last letter, but he still had no revised manuscript to submit. Gottlieb replied,

Dear Mr. Toole,

I was glad to hear from you, particularly since a week or two ago—when the year changed—I had wondered how you were coming along. My interest in the book remains what it was. I liked a lot of it a lot; thought it needed much work; and have a small doubt that something so long agonized over is ever going to live up to (at least) your own expectations. I certainly want to read it again, when you’re through doing what you’re doing.

I don’t think your purpose in writing me was vague. Everyone needs to feel outside, professional interest in what he’s doing; we live on it. But you are not working in a void, even as far as New York publishing is concerned: at least this one editor is interested. And hoping that you’ve made the right choice in continuing with this book rather than starting something new. But that decision has been made; now to see what you do with it. Onwards. Best, Bob Gottlieb.

It had been more than two years since Gottlieb first read the manuscript, and he still remained open to it. Over the course of their correspondence, Toole received more compliments and criticism, more attention from a New York editor than many writers will ever receive. But Gottlieb never offered pure praise. He was known for being courteous and direct. And while Gottlieb has long been vilified as the one that ruined Toole, there was no way for him to understand the pressure building inside the Toole home. As evident in his replies, Toole was deeply impacted by Gottlieb’s criticisms. But it may have been difficult for Toole to keep a clear perspective on that criticism if boundaries between work and family, between his professional writing career and his relationship with his mother were not upheld. From what Polites witnessed on several occasions, Thelma ranted and raged but did not comfort her son with sympathy at a moment he may have needed it most.

Toole and Gregory became good friends, enjoying morning and afternoon walks to and from campus together. Gregory had lived in Paris where she studied sculpture under Antoine Bourdelle and befriended mythologist Joseph Campbell. Her artwork adorns buildings and public spaces throughout Louisiana. Her statue of Jean Baptiste de Bienville, the founder of New Orleans, stands proudly in the French Quarter. Nearing her mid-sixties, she had already led an exciting and successful career as a sculptor. And so the two artists, one famously trained by a master and recognized in her own day and the other a bright scholar and writer who suffered the woes of dejection all too common in the arts, must have had riveting conversations strolling under the live oaks of Uptown. In the afternoon they would stand at the corner of Hampson and Pine, talking for what seemed to be hours. They may have discussed her recent projects working toward a Louisiana statue at Gettysburg, or perhaps his attempts at publication. Or it might have become more personal, perhaps about his struggles at home. Whatever they discussed, Toole had found a friend with whom he could share the final moments of the day before returning to his parents for the evening.