In the corner of my room, I have a bookshelf, with one row dedicated to books I have to read for English class. After they get their time to shine, they return back to the shelf to rot, dust collecting between the pages. I’m sure that this is an experience most high schoolers can relate to. I mean, how many times have you picked up “The Catcher in the Rye” after reading it freshman year? One or two times? I’ve never really read a book in English that I fully resonated with—one that I would want to reread. But Upper School history teacher Robert Kyff cannot say the same.
Mr. Kyff first picked up “The Great Gatsby” in a college English class. He fell in love with its uniqueness. “Passages in there that are just so eloquent and original,” Mr. Kyff noted. “I don’t think there’s a cliché in the novel.” You would think that one or two reads would be enough; three is kind of pushing it. But Mr. Kyff could not get enough. Every summer after first reading the tragic novel, Mr. Kyff finds time to reread the book. He says he’s read it around 50 times! Each time he picks up a detail he’s never noticed before; Mr. Kyff has never gotten bored of it. So he took his passion for the book and decided to write his next book on “The Great Gatsby.” Yes – his next book.
Mr. Kyff is a veteran author who has written five books. His books are composed of numerous writings from his “Word Guy” column in the Hartford Courant, in which he’s been publishing since 1992. His writing tends to focus on word origins, explaining his well-earned nickname “The Word Guy.” He also writes about word usage and pronunciation, occasionally making quizzes to keep his readers engaged. He has been writing this column for around 20 years and loves researching and writing outside of being a dedicated AP United States history teacher at KO.
The Word Guy self-published his first book, “Word Up!” in 2000, followed by his second book “Once upon a Word.” He has had numerous other books published since, including his most recent book, “Mark My Words.” Mr. Kyff described the writing process as easy; during the revision process, he only had to make minor changes and piece everything together. He said it was especially light compared to what it’s like writing this current book.
Mr. Kyff has been in the process of creating a book about the hidden aspects of “The Great Gatsby,” since spring of 2022. With his lifelong passion for English, history, and “The Great Gatsby,” writing a book to commemorate the novel’s 100-year anniversary seemed like a no-brainer to Mr. Kyff. The only problem: he was in uncharted waters. Mr. Kyff had never had to sit down and write a book from scratch; his other books were a collection of columns he had previously written. He had no idea the time it would take, considering he can finish writing 400-word columns in around four hours. So, he went to our librarian, Mrs. Solomon, for help. “He just mentioned it to me at the end of the school year,” Mrs. Solomon recalled. “And I said, oh, I have some secondary sources on ‘The Great Gatsby.’ He wanted to make sure everything he wrote was completely original. And I said, let me go into the secret stash of books that I have hidden in the storeroom. He took all the books, and he read them over the summer and…he was really excited about it.”
For those who have yet to explore the tragic novel in your English 4 class, the book follows the story of Jay Gatsby and his love for Daisy Buchanan. “It has a beauty to it and a sadness to it,” Mr. Kyff noted. “It’s about losing innocence and longing for the past, but also hope for the future.” As mentioned above, everyone at KO reads the book at the end of their sophomore year. Mr. Kyff actually sat in on a couple of sophomore English classes and listened to the points some students brought up – some of which he may be incorporating into his novel.
Mr. Kyff has been writing the novel for around two years now and is enjoying this new perspective on writing novels, though it has proven hard at times. When asked if he had any advice for young authors, Mr. Kyff responded inspirationally. “You have to be resilient, and you have to be persistent and disciplined,” Mr. Kyff exclaimed. “There’s a certain joy just in the creation, whether or not anyone else reads it.”
Mr. Kyff would like to publish his yet-to-be-named book by the 100-year anniversary of “The Great Gatsby” in 2025, but he is not against publishing it later. The Word Guy is looking forward to his book’s premiere but assured me that he doesn’t write for the money; he writes because he wants to spread his passion and knowledge, something that truly speaks to his pure character. Upper School history teacher Peter Jones describes Mr. Kyff best. “Mr. Kyff is one of the kindest, most thoughtful humans I’ve ever met,” Jones said, with a smile lighting up his face. “He cares deeply about people, his students, his friends, and his colleagues.” And it’s not just Mr. Jones that feels that way – Mrs. Solomon shared similar sentiments. “He is so kind, friendly, funny and generous,” she said with a laugh. “And he’s just a wonderful human being.”
Mr. Kyff left me with a metaphor, in which he compared himself to Gatsby. “I compare myself to Gatsby in a way, because he had this dream of marrying Daisy, his girlfriend from five years before,” Mr. Kyff explained. “And of course, it’s very difficult to fulfill that dream. So I had this dream of writing this great analysis of Gatsby, but it’s proven a lot harder than I thought.”
We wish Mr. Kyff the best of luck on the rest of his writing journey, and we cannot wait to read his new book!

