How much would Jobs have made if he had held on to those options?

His 10 million shares are now worth $1.2 billion. So he isn't hurting. (And he has made much more on stock in Pixar, which is now part of Disney ( DIS).)

As for those canceled options?

Try $5.6 billion.

Or ... $4.4 billion more than Jobs has made on the shares he took in exchange.

Jobs was not alone. Around the same time, in March 2003, others at the company were allowed to make a similar exchange. Many employees were holding bubble-era options that also seemed worthless because their strike prices were so high. So in March 2003, Apple set up a one-time program to let them swap these options for a smaller number of options at a lower strike price.

Bottom line: The exchange would benefit them so long as the share price stayed low. They would lose out only if it went to the moon.

Oops.

In total, the company canceled 20 million options (in today's terms). The move will have cost those employees, and saved shareholders, hundreds of millions of dollars.

All of which should offer at least a smidgeon of consolation to those who missed out on Apple stock. Why? Because it shows that four years ago, not even Steve Jobs, or other folks at Apple, dreamed the shares could possibly come this far.

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In keeping with TSC's editorial policy, Brett Arends doesn't own or short individual stocks. He also doesn't invest in hedge funds or other private investment partnerships. Arends takes a critical look inside mutual funds and the personal finance industry in a twice-weekly column that ranges from investment advice for the general reader to the industry's latest scoop. Prior to joining TheStreet.com in 2006, he worked for more than two years at the Boston Herald, where he revived the paper's well-known 'On State Street' finance column and was part of a team that won two SABEW awards in 2005. He had previously written for the Daily Telegraph and Daily Mail newspapers in London, the magazine Private Eye, and for Global Agenda, the official magazine of the World Economic Summit in Davos, Switzerland. Arends has also written a book on sports 'futures' betting.

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