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He doesn't have to sell. He can finance the deal with debt backed by his newly risen stock as collateral. Then the debt is used to further inflate the price of the stock.

The flywheel metaphor is pretty apt.

It is us, index fund owners :clown:

Disclaimer: I also have a small amount of money in vanguard IRA

According to the image of the steps, Oracle’s share price is going up, presumably more than it would have without engaging in these steps. How can that cost index fund owners? They would be benefiting from the share price increase.

Ultimately, debt will fuel this. Oracle can't pay with cashflow.

Credit.