How I Got a Novel Published and What Went Wrong
As I’ve mentioned in previous posts, in 1992 I was courteously asked to move on from the law firm where I was an associate and had to decide whether to stay in the profession or try something different. Instead, I pushed it off, living on savings while I took up such early mid-life crisis activities as learning guitar. Another lifelong goal I pursued that year was writing. Since boyhood, my dream of being an author – in 7th grade, after reading F. Scott Fitzgerald’s This Side of Paradise, I briefly signed school papers “H. Michael Sawikin” – had done battle with my desire for a stable career and financially comfortable life. It would’ve been surprising if, as the child of very anxious Holocaust survivors, I didn’t have the latter force strong inside me.
My first writing idea was to get into TV, which seemed to combine the creative and the practical, if you could land a staff job somehow. I bought a PC and screenwriting software and knocked out spec scripts for L.A. Law and Seinfeld. The latter was in its second season and not yet popular, but I loved it and thought, as an Upper West Side Jew, I shared its sensibility. I was able to get my Seinfeld script to the producers through a childhood friend, the great SNL writer Robert Smigel, and soon I received a call from one of them, Larry Charles. He said the script was funny, but he couldn’t pass it on to Larry David because the story was at the same time “too set up and not set up enough.” I had no idea what he was talking about, though in hindsight I can see that they were developing the interlocking-plotlines template that raised the show to genius level by its third season.
Charles suggested I give it another try. Clueless as I was about the wild improbability of an uncredited writer getting a call from a producer, instead of just thanking him profusely, my practical side made me ask whether, if I wrote a usable script, I could get a staff job. He said there were “so many people” ahead of me, it was hard to see that happening anytime soon. I decided to focus my efforts elsewhere, while of course Seinfeld and the Larrys Charles and David went on to make TV history.
I turned to an idea for a novel that had emerged from a short story I’d just finished, “The Great Judge.”1 The eponymous judge, Leo Fineman, was inspired by Irving Kaufman, most famous for sentencing Julius and Ethel Rosenberg to death in the 1950s. The story’s protagonist was Fineman’s clerk Rick Green, a 25-year-old Harvard Law (like me) and Columbia (also me) graduate. I knew what went on between Kaufman and the clerks he tormented because in 1985 I had worked across the hall for a senior judge named J. Edward Lumbard. (A blueblood WASP, Lumbard wore the first initial-middle name comfortably.)
In the short story, Green manages Fineman’s volcanic temper while inducing him to grant a habeas corpus petition for a prisoner he believes was wrongly convicted. As I wrote the story’s conclusion, I began to wonder what would happen to Green after he went to a law firm and whether in a novel I could show the life of an associate more accurately than I’d seen in fiction before. Also, my father, whom I’d given a cameo in “The Great Judge,” was enough of a “character” in real life that I was interested to see what he might do in the space of a full-length book. If I hadn’t had this foundation to build on, I probably wouldn’t have set out on the daunting prospect of a novel. This leads to my first tip for the aspiring novelist: start with a story or fragment and see if it wants to take you anywhere bigger.
Again, armed with the cluelessness that has blessed me my whole life, I seem to have assumed I could sell the book when it was done, despite never having published anything except one humor piece in the Village Voice, or attended any writers’ workshops, or knowing any writers at all. Or, and I don’t really remember, I just had to get the story out, even if I was writing for myself. This is my second piece of advice: write something that you need to say and that you would want to read yourself, not what you think is commercial.
As the plot took shape, I combined elements of law firms I’d worked at into the Dickensian-sounding Crank, Wilson & Shapiro. Two M&A transactions I’d been on — a hostile takeover of a Georgia textile firm and the LBO of a Wisconsin manufacturer — were the source material for the deal Green is assigned to and on which he insider trades, driving the action in the second half of the book.2
My father was dropped, undisguised, right into the book as Fievel Green, who becomes implicated in the insider trading. A childhood friend, with whom I’d reconnected in my 20’s, became the model for Rosen, the junior arbitrageur who corrupts Green. Two of my former girlfriends, one a Southern blonde and the other an observant Jew, inspired the women Green is torn between. The details of the insider trading investigation and Green, Rosen, and Fievel’s cat-and-mouse game with the SEC were all fictional (with advice from criminal lawyer contacts). Surprisingly, or not so much, as many novelists discover, readers have told me that the fully invented parts of the novel are the most believable.
Unlike the easygoing guy I am now, at the time I was bursting with hostility toward the legal profession that I felt had rejected me, toward Wall Street, toward organized religion and the UJA, plus any girlfriend who had hurt my feelings. My depiction of Irving Kaufman is particularly savage. But “anger is an energy,” as John Lydon once sang – it fuels art. As the book progressed, however, I found myself rethinking the source relationships, advocating for the characters they had inspired and making them rounder, while Green’s shallow initial perceptions and self-serving justifications are dismantled. Green himself does grow up and learn something by the end which would, come to think of it, have disqualified me for the Seinfeld staff, where the rule famously was “No hugging, no learning.”
A writing exercise I found useful in weaving together my three storylines – LBO, insider trading, and Green’s love life – was to draw a circle and place each character along its circumference, like numbers on a clock. I drew lines connecting every character with every other one and above each radius jotted a note summarizing their relationship – helping me see how it could advance one or more of the plot elements. While I won’t claim the book’s structure paid off as well as the “Soup Nazi” episode of Seinfeld, by the end I did catch all the balls I was juggling and get them back in their box. Larry Charles would’ve approved.
The novel makes some larger points, although I didn’t initially know what they were. When I started writing, all I had were some characters and a couple of story ideas. That’s my third tip, put best by Arthur Miller, who said that when he was writing a play and discovered what it was about, he wrote it on a strip of paper and taped it to his typewriter. You don’t have to start your novel with a message, in fact it’s better if you don’t – just tell an honest story and something will emerge.
I treated the process the only way I knew how, as a 9-to-5 job. I would shower, get dressed, then walk across the bedroom to my desk and write, with a break for lunch and maybe a run, until my wife came home from work, and I punched out for the evening. Most days I would start by listening to the then-new R.E.M. album Automatic for the People to get into an emotional and creative mood (the last three songs really work). After eight months, I had a draft and a title, Rick Green, Esquire. Now came the little matter of getting a publisher.
Here I had a stroke of luck, as my wife was a fiction editor at Good Housekeeping magazine alongside a woman named Phyllis Levy, a publishing legend. (Phyllis was partly the model for a character in Rona Jaffe’s breakout novel, The Best of Everything, about young career women in 1950’s New York.) Phyllis read my draft, loved it, and passed it on to an agent friend, Georges Borchardt. The idea that Borchardt, then representing important authors of literary fiction like Francine Prose and Louis Begley, might take on a plot-driven novel with intentionally mainstream appeal, thrilled me.
The first feedback I got via Phyllis was that Georges thought I had a “real voice” and if the rest of the book was as good as the beginning, we had something publishable. Within days, he’d agreed to take me on, and we were lunching at his customary corner table at Trattoria Dell’Arte. I felt I was joining the “literary community” and pictured a string of novels, perhaps some prizes. (Also, should I go back to H. Michael?) But it didn’t work out that way.
In part two I will tell how we got a publisher and what went wrong. I will touch upon anti-Semitism, although I won’t blame the book’s disappointing performance on that – well, maybe a little.
P.S. I’m the anti-Semite.
“The Great Judge” was the prologue to the original 1995 Simon & Schuster version of my novel, The Education of Rick Green, Esq., but I omitted it when I republished the book in 2017 on Amazon after the rights had reverted to me.
Interestingly, a subsequent litigation around the failed manufacturer LBO led a plaintiff’s lawyer to call me about incidents depicted in my novel. He had somehow figured out it was the basis for the deal, though I’d never told anyone. I said, you know, the book is fiction, but I must say the lawyer’s questions were on the right track.