Options Trade Cost Steve Jobs $4 Billion

Jobs at the time was holding 15 million options at a strike price of $9.15, which means he could make money only if the shares rose above that level, plus another 40 million options with a strike price of $21.80.

The share price by early 2003: around $7.50.

Ouch.

So Jobs and the board reached an agreement. He would throw away all those apparently worthless options in return for 10 million actual Apple shares. (This information comes from the company's public filings. The prices have been adjusted to reflect Apple's 2-for-1 stock split in 2005.)

At the time, it looked like he was giving up nothing and getting $75 million in return. And, as he had rescued the company from oblivion, who would argue he didn't deserve it?

The company explained at the time that Jobs was not merely motivated by self-interest. "Mr. Jobs felt strongly that this would more effectively build shareholder value," it said in a public filing, "by reducing the company's overhang and by providing additional shares that could later be granted to employees whose contributions are critical to the long-term success of the company."

Indeed. Of course, the same would also have been largely true when Jobs had accepted the options in the first place.

Irony: The period when he made this decision, early 2003, was to prove the post-bubble low point for Apple stock. It was just before it began its monumental run.