I realize that I didn't explain this part fully. Any asset aside from cash is speculative - and is primarily determined by how much a person's willing to buy and sell it for.
So when AAPL is worth 500 billion or whatever in one day, it doesn't actually mean that AAPL can be converted into cash wholesale for $500 billion dollars - it means that for that particular day, the small percentage of trading involving AAPL shares determined that people were willing to pay for XX amount of dollar/share for the stock and multiply that by number of outstanding shares => we get the market's valuation of AAPL at that particular moment of the market's condition of supply and demand. However, in the hypothetical scenario in which Steve Jobs foundation owned 100% of AAPL and decided to have estate-sale, the market dynamics of dumping all shares of a stock onto the market is equivalent of oversupply of the stock to sell and not enough buyers, and therefore driving the stock price down.
So suppose in the "flight to safety" scenario, the equity market is shaky for whatever reason: unrest in middle east, euro crisis etc. The demand for equity is less, therefore what I paid originally for SPY (S&P500 tracking index) may be $100, but the highest someone who wants to buy it from me might be $80. But I sell it anyways because I'm driven by fear that the market's going to deteriorate further. With that money, I have only $80 worth of buying-power.
On the flip-side, as everyone's getting out of the equity market, they rush to the government bonds market as this is the safest investment. The demand for treasury bills suddenly goes up, therefore to buy your bonds; you have to be willing to buy them at a higher price than the next guy. So if I want to buy the same number of bonds previously of value $100, I have to spend now $120. So you see how now the bond market taken at wholesale is valued more.
So in your scenario, flight of safety goes like this:
Person 2: Sells equity of original value of $100 for $80 to person1
Person 1: Then has equity valued at $80 at the time
Person 2: Buys $80 worth of bonds from person 3 and now has Tbond worth $80
Person 3: Sells bonds of original value of $100 for $120; a portion of which goes to person 2