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One early reference to a trade involving nontraditional instruments and optionality appears in the Bible. Apparently, Joseph wished to marry Rachel, the youngest daughter of Leban. According to Frauenfelder (1987), Leban, the father, sold a (European style call) option with a maturity of seven years on his daughter (considered the underlying asset). Joseph paid the price of the option through his own labor. Unfortunately, at expiration Leban gave Joseph the older daughter, Leah, as wife, after which Joseph bought another option on Rachel (same maturity). Calling Joseph the first absolute manager would be a stretch. (Today absolute return managers care about settlement risk.) However, the trade involved nontraditional instruments and optionality, and risk and reward were evaluated in absolute return space.
ineichen

Gastineau (1988) quotes Aristotle’s writings as the starting point for options. One could argue that Aristotle told the story of the first directional macro trade: Thales, a poor philosopher of Miletus, developed a “financial device, which involves a principle of universal application.” People reproved Thales, saying that his lack of wealth was proof that philosophy was a useless occupation and of no practical value. But Thales knew what he was doing and made plans to prove to others his wisdom and intellect. Thales had great skill in forecasting and predicted that the olive harvest would be exceptionally good the next autumn. Confident in his prediction, he made agreements with area olive-press owners to deposit what little money he had with them to guarantee him exclusive use of their olive presses when the harvest was ready. Thales successfully negotiated low prices because the harvest was in the future and no one knew whether the harvest would be plentiful or pathetic and because the olive-press owners were willing to hedge against the possibility of a poor yield. Aristotle’s story about Thales ends as one might guess: When the harvesttime came and many presses were wanted all at once, Thales sold high and made a fortune.

Thus he showed the world that philosophers can easily be rich if they like, but that their ambition is /* unfortunately */ of another sort. So Thales exercised the first known options trade some 2,500 years ago. He was not obliged to exercise the options. If the olive harvest had not been good, Thales could have let the option contracts expire unused and limited his loss to the original price paid for the options. But as it turned out, a bumper crop came in, so Thales exercised the options and sold his claims on the olive presses at a high profit. The story is an indication that a contrarian approach (trading against the crowd) might have some merit.
This comes from chapter 1 [pdf] of Absolute Returns: The Risk and Opportunities of Hedge Fund Investing* (A. Ineichen).

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