Infinite Jest

A thousand-page novel set in a near-future North America, braided from three strands — a Boston halfway house, an elite junior tennis academy, and the search for a film so absorbing that anyone who watches it loses the will to do anything else. Addiction, entertainment and the exhaustion of irony are its subjects, and its length and endnote apparatus are part of the argument rather than incidental to it.

Why it’s on the list: One of the 25 books Tyler Cosgrove picked as the ones he would hand to someone with real leverage over American policy — the only novel on a list otherwise made of history and business.

Where I saw it: @tylercosgrove’s October 15, 2025 list of 25 books he offered to send to Jared Kushner.

Connections

• Literature — the frame this belongs in rather than any business thesis.
• Republic of Letters — the portfolio idea that covers reading fiction as its own kind of infrastructure.