Gambler

The memoir of the sports bettor generally described as the most successful in history: decades of line-shopping, syndicate building, and information arbitrage, alongside a childhood in rural Kentucky, a long fight with alcohol, and an insider-trading conviction that was later commuted. 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.

Why it’s on the list: Bold on @mastersinvest’s 2025 list, meaning the curator rated it very good rather than merely read.

Where I saw it: @mastersinvest’s “2025 Reading … so far” list, August 20, 2025, where it appears in bold. The full 46-title list is transcribed on 2025 Reading So Far… (tweet).

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.