Typewriters, Dictaphones and Kools: What It’s Like to Work for J.D. Salinger’s Agent

It was 1996 and Joanna Rakoff was 23. After abandoning her plan to become an academic, she found herself, like many other young liberal arts grads with literary aspirations, working as an assistant in book publishing.

Joanna Rakoff
Joanna Rakoff (photo credit: David Ignaszewski)

It was 1996 and Joanna Rakoff was 23. After abandoning her plan to become an academic, she found herself, like many other young liberal arts grads with literary aspirations, working as an assistant in book publishing.

Sign Up For Our Daily Newsletter

By clicking submit, you agree to our <a rel="noreferrer" href="http://observermedia.com/terms">terms of service</a> and acknowledge we may use your information to send you emails, product samples, and promotions on this website and other properties. You can opt out anytime.

See all of our newsletters

“There were hundreds of us, thousands of us, carefully dressing in the grey morning light of Brooklyn, Queens, the Lower East Side, leaving our apartments weighed down by tote bags heavy with manuscripts,” Ms. Rakoff writes in My Salinger Year, her new memoir that comes out next week about the year she spent as an assistant at Harold Ober Associates, a literary agency best known for representing J.D. Salinger.

One of Ms. Rakoff’s tasks was to respond to the steady stream of fan mail for the legendarily reclusive author. Ms. Rakoff was given a typed-up form letter from 1963 to copy, informing the fans that the author did not wish to get letters from readers.

The letters, many of them handwritten, were personal and passionate. There were old men who had served with the author in the war and young people discovering the hypocrisy of the real world for the first time. Ms. Rakoff went off script and began to write back, giving the fans her own advice and opinions, mediating between Salinger and his fans.

Although Salinger’s larger-than-life presence, or really absence, casts a shadow over My Salinger Year, the book is really about first jobs and navigating adulthood. Ms. Rakoff’s life had shifted. Instead of moving to Berkeley to be with her college boyfriend, she lived with a socialist would-be author in an apartment without a kitchen sink in Williamsburg, which was then in the early stages of gentrification.

“That time in your life is a really hard moment,” Ms. Rakoff told me over tea in her airy apartment in Cambridge on a recent afternoon. “You’re so clueless and don’t yet have your own sense of agency.”

My Salinger Year is a book that Ms. Rakoff, who mostly writes fiction and journalistic essays, had been asked to write for years. Memoir presents the challenge of examining one’s own life, something that Ms. Rakoff said doesn’t come naturally to her.

“There is the obvious fear in writing a memoir of realizing that the characters are real people and are going to read it,” Ms. Rakoff said. “But then there was also the fear of having to delve back into myself.”

Over the course of writing the book, her life seems to have shifted back, in a sense: Ms. Rakoff, now 41, left her husband and New York and got back together with her college boyfriend. They now live in Cambridge, where he teaches music composition at MIT.

“I am not a super reflective person. I don’t mean that I’m very superficial, but I don’t have the personality of writers who document their lives and feel very comfortable talking about themselves,” she said. “It was good to be able to have a moment to examine my life and be self-aware.”

Even by the standards of the publishing industry, where modernization is slow, Harold Ober was old-fashioned. In 1996, Ms. Rakoff remembered, many of her friends were working for dotcoms. Publishing houses, a few years behind, were embracing the Internet age. Not Ober.

Phyllis Westberg, the agency’s president and Ms. Rakoff’s boss (although both the agency and Ms. Westberg are unnamed in the book, Ms. Rakoff identified them in a 2010 Slate piece), used a dictaphone to correspond with editors and authors. Ms. Rakoff would listen to her boss’ voice on the miniature cassette tapes and, using a foot pedal to control the speed and a typewriter, transcribe the contents. Contracts were recorded on preprinted, color-coded cards that were folded in half and stored in fireproof cases around the office. When a check came in, the card was retrieved and brought to the accounting department. They entered the information on the card by hand and manually cut a check. Each agent circulated folders around the office filled with the week’s correspondences.

Midway through Ms. Rakoff’s time at Ober, the office got its first computer.

I was also Phyllis Westberg’s assistant. Like Ms. Rakoff, I was 23 and stayed for a little over a year. It was 2008, not 1996, but little had changed in a dozen years. The dictaphone and typewriter, outdated in the mid-90s, were still in use.

Also like Ms. Rakoff, I stared at the typewriter on my first day, wondering why it wasn’t working. Finally, someone showed me how to turn it on.

I did have a computer on my desk. But my boss didn’t. I was tasked with printing out my employer’s emails. I scurried around the office to find hardcopies of earlier correspondence related to the email and brought it to my boss.

As she smoked Kools at her office desk, she would dictate her responses. “Send it off,” she would say, gesturing into the ether, after I showed her a printed draft.

Although by then computers were a necessity, Ms. Westberg was wary of them and saw them as a distraction.

“Stop playing on your machine,” was a common refrain when she caught me using the Internet. “What is that, ‘SpaceBook,’” she would say, conflating social networks.

One of my jobs, and one of the few things that my boss approved of using the Internet for, was scouring eBay for people illegally selling Salinger stories that had run in The New Yorker but, as per the author’s request,  had never since been published. I sent cease and desist letters, informing the seller that he or she was violating copyright law.

One thing had changed: By the time I worked there, Salinger was completely deaf and didn’t call the office. Most interaction took place through the mail.My Salinger Year by Joanna Rakoff

Ms. Rakoff had a great deal of contact with Salinger during her time as an assistant at the agency. That’s because Salinger was working on something new.

After very publicly not publishing new material or allowing excerpts of his work to be included anywhere, the author decided that a story he wrote for The New Yorker in 1965 could be made into a book. Roger Lathbury, the publisher of a small academic press in Virginia, had written to Salinger eight years earlier to ask if he could print the story. After thinking it over for almost a decade, Salinger shocked everyone at the agency when he decided to take Mr. Lathbury up on the proposal. It made for some excitement in the mostly quiet office.

Mr. Lathbury began calling Ms. Rakoff with concerns and questions. There were a lot of details to work out. The contract that the agency drew up gave Mr. Salinger all the power and was very detailed in terms of specifics such as paper stock and binding. The project brought phone calls from Salinger, many of which were fielded by Ms. Rakoff. At one point, he even visited the office, the first time he had been back to New York in years. (He moved to Cornish, N.H. in 1953)

Ultimately, the project ended abruptly when Mr. Lathbury told a magazine about the book, losing the trust of the publicity-shy author.

My time at the agency started out slowly, until a Swedish humor writer wrote what was presented as a sequel to The Catcher in the Rye, sparking new Salinger drama. Salinger sued for copyright infringement and won.

Any Salinger-related news generated a great deal of publicity. Journalists whose bylines I recognized would call the office, most likely, I now realize, knowing that they wouldn’t get a quote but could write that the agency declined to comment. At the time, I remember wondering why the reporters were wasting their time. Surely Salinger and his agency’s policy of refusing to talk to the press were well-known.

The press phone calls stopped after that but it wasn’t long before they would begin again.

On January 28, 2010, Phyllis called me into her office and handed me a tape. There was no backup: no prior email correspondence, no colored cards with faded pencil marks, no contracts with yellowed edges. “I need this right away,” Ms. Westberg said solemnly. “And don’t tell the other girls about this,” she cautioned, pointing at the assistants.

The only thing I could imagine, as I walked back to my desk, was that the agency had been sold, disbanded or folded.

I put the tape in the player, put on my headphones and positioned my foot over the pedal. I learned the news as I typed: J.D. Salinger had died the night before.

I hurried to show Phyllis a draft of the announcement. After she gave her approval, she followed me to tell the others in the office that Jerry had died. She was very sad and the mood in the office was somber.

Following her instructions, I found the fax numbers for The New York Times and The Associated Press in the ancient Rolodex at reception. Since the contact information for the Times hadn’t been updated when the paper moved its headquarters to Eighth Avenue three years earlier, the AP beat the Times and broke the story.

The phone rang almost immediately and continued for days. It was a jarring sound in the usually silent office. My boss, grieving for her longtime client, momentarily brightened when flowers from Salinger’s publisher Little, Brown arrived. I realized that, to my boss, Salinger was more than a public persona. For her, the loss was personal.

Ms. Rakoff writes about a similar realization when recounting Salinger’s visit to the office:

“The obvious occurred to me: She truly liked Salinger. Adored Salinger. Her job–and I already knew this–was far more than a job to her. But so much of her work involved tending to the interests of the dead I hadn’t thought at all about what such devotion meant in terms of her relationship with the living. She was Salinger’s conduit to the world, his protector, his explainer, his mouthpiece. She was a part of his life; and he hers. She was his friend.”

The agency loyally defended Salinger’s privacy. During the time I worked there, the question I was asked most frequently when I told people where I worked was whether Salinger was still writing. Were there more books? Everyone had heard rumors. I deflected everything, explaining that even if my boss knew, she wouldn’t tell me.

Ms. Rakoff was worried about her old employer’s reaction when she wrote her earlier essays about her time at the agency. Former employees who discussed Jerry were spoken of with disdain. They had betrayed the mission of the agency.

“I was terrified that Phyllis was going to hate it because anything about Salinger is like a breech of privacy,” Ms. Rakoff said. “It had been a while since I worked there but I still felt inculcated in the agency culture.”

Ms. Rakoff didn’t attempt to interview her former boss. There is no way she would have given an interview. Both Ms. Rakoff and I could picture her, smoking as she talked about the audacity of an interview request.

I had managed to forget many of the odd details about the agency and the particular experience of working at an office that was frozen in time, whether in 1996, on the precipice of the digital era, or 2008 just before a global recession and the slow death of print. Ms. Rakoff’s descriptions brought it all back, from the Kools to the clicking of typewriters.

“I was such a child when I worked there,” Ms. Rakoff said.  “Part of what happened to me over that year was I started to see all the ways that the agency didn’t function.”

In the process of writing the book, Ms. Rakoff interviewed many of her former colleagues about their experience and finally understood some of the conversations she had overheard and letters she had typed. She was reminded of many of the every-day minutiae that so eerily conjured my own experience.

When I was hired at Ober, I asked my boyfriend at the time if he thought I should take the job. “No matter what,” he said, “working for Salinger’s agent will be a good story.”

Typewriters, Dictaphones and Kools: What It’s Like to Work for J.D. Salinger’s Agent