By Philip Elmer-DeWitt
January 24, 2008

It may come as some consolation to the investors who lost their shirts as Apple (AAPL) shares collapsed over the past month that nobody lost more, at least on paper, than its CEO.

As the company’s largest individual stockholder, with 5,546,451 shares directly owned, Steve Jobs (were he paying attention) could have watched the value of his holdings drop from $1.126 billion just before Christmas to $771 million at Wednesday’s close, a paper loss of $354 million.

Over at Walt Disney Co. (DIS), where Jobs is also the single largest stockholder, the news is even more grim. The value of the 138 million Disney shares he owns (thanks to the sale of Pixar two years ago) fell from a pre-Christmas high of $4.588 billion to $3.935 billion yesterday, a loss of $652 million.

That’s a total hit of just over $1 billion in the space of a month.

Of course, these are just paper losses. Like any shareholder, Jobs doesn’t actually lose a penny unless he sells his stock at the lower price. But given the fact that his annual salary is once again a symbolic $1, this might not be a bad time for Apple’s board to start looking for another way to compensate its hard-working CEO. At least that’s how Fake Steve Jobs sees it:

I just called Peter Oppenheimer and told him to get into position with the options machine and be ready to begin firing on my order. We’re going to wait and see how bad things get today. I think this might be a golden opportunity for a handful of top insiders to make some quick money. Ideally we’d like to see the stock get down below $100. Keep your fingers crossed! Daddy needs a bigger jet. (link)

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