Gambler

Why it’s on the list: The memoir of Billy Walters, the sports bettor generally described as the most successful in history — decades of line-shopping, syndicate building and information arbitrage. The betting chapters read as a book about edge and bankroll: how to size a position when you are right slightly more often than the market, and how to survive the stretches when you are not.

Where I heard about it

• @mastersinvest — on his “2025 Reading … so far” list, August 2025, in bold — his mark for “very good” rather than merely read. The full 46-title list is transcribed on 2025 Reading So Far… (tweet).

About this edition

Alongside the betting, the book covers a childhood in rural Kentucky, a long fight with alcohol, and an insider-trading conviction that was later commuted.

Connections

• 2025 Reading So Far… (tweet) — the list this came from.
• Risk — a career built on pricing it rather than avoiding it.
• Risk Management — bankroll discipline is the book’s actual subject.