| Y/M/D | Description | Place |
|---|---|---|
| 1929/09/00 | While visiting Hollywood, Churchill invest half of his 22,000 pound ($1,650,000 in 2015) publishing advance in American stocks through E F Hutton. | |
| 1929/10/18 | Churchill's gains with E F Hutton doubled to $420,000 ($6.3 million in 2015). | |
| 1929/10/24 | Churchill visits the NY Stock Exchange. At the opening bell, share prices fell by an average of 11 percent. Bankers slowed the panic by authorizing the exchange to bid for large blocks of leading shares. The Dow Jones index closed down 2 percent. | New York Stock Exchange, New York City |
| 1929/10/25 | On the advice E F Hutton broker William Van Antwerp, Churchill purchases another $26,500 ($397,500 in 2015). | |
| 1929/10/28 | New York Stock Exchange loses 12.82 percent of its value. | New York Stock Exchange, New York City |
| 1929/10/29 | Dow Jones index loses another 12 percent, dropping $14 billion in value. During the course two trading days, $30 billion of the market's $80 billion value had vanished. | New York Stock Exchange, New York City |
| 1929/10/29 | At the close on Tuesday October 29th, the Dow Jones index has lost another 12 percent. During the course of two trading days, $30 billion of the market's $80 billion value has disappeared. | |
| 1929/10/29 | On his voyage back to England, Winston Churchill uses the ship's ticker tape to calculate his losses. The tape did not stop reporting the market crash until 7:45 pm. Churchill almost certainly lost more than $75,000 ($1,125,000 in 2015). | |
| 1929/10/30 | Carl Fisher loses his fortune in the Wall Street Crash of 1929 | |
| 1929/10/30 | Bernard Baruch feeling partially responsible, gives Churchill a $7,200 ($108,000 in 2015) personal profit he had made on a single share. | |
| 1929/12/00 | Dr Hollands loses the Hood house and other properties after the stock market crash of 1929. | Hood-Strickland House, Smithfield, NC |
| 1933/03/15 | The Dow Jones Industrial Average gains 15.34 percent of its value to close at 62.10. |
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