According to @QCompounding, Jesse went bankrupt after bad advice, rebuilt multiple times, then in 1929 shorted into market euphoria, split orders across more than 100 brokers to conceal intent, and exited the crash with $100 million, underscoring a contrarian short setup with stealth execution in high-sentiment markets.

According to @StockMKTNewz, the S&P 500’s largest single-session losses include Oct 19, 1987 (-20.5%), Oct 28, 1929 (-12.3%), Mar 16, 2020 (-12.0%), Oct 29, 1929 (-10.2%), Nov 6, 1929 (-9.9%), Mar 12, 2020 (-9.5%), and Oct 18, 1937 (-9.3%) (source: @StockMKTNewz on X, Dec 28, 2025). The post presents these as part of the top 10 worst days in S&P 500 history, providing concrete reference points for historical drawdown risk sizing, stress testing, and volatility scenario planning across risk assets, including crypto (source: @StockMKTNewz on X, Dec 28, 2025).

According to @business, Andrew Ross Sorkin’s new book ‘1929’ re-creates the euphoria and mania that led to the most famous stock market slump in history, underscoring historical conditions that preceded a severe drawdown (source: Bloomberg @business, Oct 18, 2025). The linked Bloomberg coverage frames the book as a lens on today’s stock market, positioning its historical narrative as context for evaluating current risk sentiment and speculative excess (source: Bloomberg @business article link referenced in the post). For traders, this highlights the value of studying pre-crash exuberance when monitoring sentiment extremes and risk management in heated markets (source: Bloomberg @business).

According to Compounding Quality on Twitter, Jesse Livermore is renowned for making and losing one of the largest fortunes in Wall Street history, notably predicting the 1929 crash and earning $100 million before losing it all (source: @QCompounding, June 3, 2025). For active traders, Livermore’s disciplined approach to risk management and market timing remains relevant, especially in the volatile cryptocurrency markets where history often repeats itself. Understanding Livermore’s methods highlights the importance of capital preservation and trend following, key principles that apply to both traditional stocks and digital assets.