

You can gamble on whether a stock price will rise or fall. When going to war, stock prices for war companies rise because they are expected to get a lot of business, but if that call to war is suddenly canceled, then the stock price for that company decreases.
If he made a losing bet, one of two things happened:
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The value of the stock was going to drop way below the value it started at, so he would earn a large payout on that gamble.
-
He was funneling large amounts of money to other insider traders.




You can trade outside of trading hours by paying extra for the trade. When you do this, you can buy/sell only to others who have also paid extra. This means you have some extra control over who gets your shares and when. In addition, you can sell shares directly to other people anytime if you physically own them.