After four years of intense research and reflection, Upper School history teacher Rob Kyff has published “Gatsby’s Secrets,” a deep dive into the themes, characters, and prose of F. Scott Fitzgerald’s “The Great Gatsby.”
Mr. Kyff, who first read the classic in college, was captivated by its language and atmosphere. “I would read it every summer,” he said. “There was always something new I noticed.” Though he never had the chance to teach the novel during his decades as an English teacher, it remained a constant literary companion.
When the pandemic slowed daily life, Mr. Kyff finally had the time to act on years’ worth of informal notes. “The first thing I did was write down all the different themes and elements I wanted to explore – flowers, rain, cars, water, everything,” he said. “I ended up with about 150 categories.” He then dove into decades of literary criticism, compiling and categorizing insights from over 50 writers. In total, he amassed over 1,200 pages of notes.
Instead of organizing the book by chapter, Mr. Kyff structured it around broader topics that appear throughout the novel, such as humor, sports, and overlooked characters. One example is Michaelis, the Greek man who stays with George Wilson the night before Gatsby’s murder. “He really tries to help him,” Mr. Kyff noted. “I wanted to show characters like that from multiple angles.”
“Gatsby’s Secrets” also addresses deeper themes, including the ambiguity of the American Dream. Mr. Kyff sees Gatsby as both a tragic and inspiring figure. “There’s something admirable in how he keeps trying,” Mr. Kyff explained. “He’s completely committed to this ideal, even if it’s flawed.” Gatsby, Mr. Kyff argues, represents a blend of the materialistic and spiritual versions of the American Dream. “He uses wealth to pursue something higher, something almost heavenly,” Mr. Kyff stated.
The book was a collaborative effort, too, as some of Mr. Kyff’s own students and colleagues helped proofread the manuscript, giving feedback and catching errors. “They were a huge help,” he mentioned.
After struggling to find a literary agent, Mr. Kyff self-published the book through digital publishing, which made it available on Amazon. “It was very satisfying,” he said. “I felt like I was in contact with a great book–with great language–for four years.”
For students who’ve studied “The Great Gatsby,” “Gatsby’s Secrets” offers a fresh, multifaceted perspective on a familiar text. As Mr. Kyff puts it: “It’s like reading Shakespeare – you never really get to the bottom of it.”

