From crossword to crossplay: tracking relationship repair between The New York Times and its audience from 1942-2026

Journalism’s future is precarious. Longstanding business models based on advertising and print subscriptions have crumbled, and the internet-fueled influx of quasi-journalistic actors has threatened the field’s authority, legitimacy, and credibility. When faced with vulnerabilities to economic and cultural stability, news organizations often reach out to their audiences, hoping to repair a fractured organization-audience relationship. This dissertation zooms in on perhaps the most successful iteration of this: The New York Times’ puzzles, from crosswords to its most recent game, Crossplay. It details how the Times’ puzzle has been linked to institutional, industry, and media regime change, from the first crossword published in the wake of the Pearl Harbor bombing to the newspaper’s purchase of Wordle amid the COVID-19 pandemic. It also shows how the Games product’s immense popularity in 2026 is the result of the organization addressing, for the first time, economic and cultural capital together. Historically, the puzzle has been used to engage the Times’ audience in a strictly economic or cultural sense. For the first few decades of crossword publishing, the Times treated the puzzle with relative independence, growing its cultural capital exclusively. In response to strain in the 1960s, the Times began profiting off its puzzle products, namely through consumer products. Cultural value, however, remained under the purview of the crossword editor alone. This parallel development of cultural and economic capital continued until a leaked 2014 “Innovation Report” showed how, internally, the Times realized it could no longer ignore the dual threats to its cultural and economic stability. The Times created the Mini Crossword and Spelling Bee, hired additional editors, and established digital-first puzzle production processes. For the first time, the organization addressed the puzzle’s cultural and economic growth together. Measured by pageviews or digital subscriptions, the Games product has shaped the Times into one of the only profitable newspapers today. This research finds the Times’ recent success is largely due to three changes rooted in an appreciation for puzzles’ economic and cultural capital: (a) the embrace of technology in game design, (b) the hiring of diverse, creative puzzle constructors, and (c) the increased resources provided to create a formalized game development process. When the Times acquired Wordle in 2021, it may have seemed like “lightning in a bottle.” But the game’s enduring success is owed to the institutional scaffolding that integrated new technology into game development, that brought about more creative, diverse game constructors, and that provided ample resources for its workers to do their work. The Times, therefore, has improved its organizational-audience relationship through Games by addressing both dimensions of journalism’s contemporary vulnerabilities together. This research contextualizes newspapers’ historic audience engagement and relationship repair practices, considers the ways the industry misattributes “newness” and “innovation” to journalistic products at times, and reflects on why puzzles that have little to do with journalism have become so important to one of the most impactful journalistic organizations in the world.