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They've all held those jobs since Apple's Dark Ages (the late 90s)

Oppenheimer was brought in after the backdating scandal, when Fred Anderson was let go. Anderson actually had a big role in saving Apple under Gil Amelio, since he helped arrange a large bond issue which kept Apple from literally running out of money:

The paper also suggested selling convertible debentures, a type of bond, for around $500 million. To help the plan along, Amelio hired Fred Anderson as the new CFO to replace Graziano.

...

Amelio started working with Fred Anderson on preparing Apple's debenture sale. They were working an impossible schedule. Mike Townsend predicted that Apple would be insolvent by April. That left only two months for the sale.

Typically a company's senior executive would travel around the country making presentations to possible buyers for about three weeks and then set a deadline for buying about a month after the last presentation. Not only did Amelio not have that kind of time (if Townsend's predictions were true), he would not be able to leave the company for that long right after he joined it.

http://lowendmac.com/orchard/05/gil-amelio-apple.html



True, Oppenheimer became CFO of Apple in 2004, replacing Fred Anderson. But he's been with Apple since 1996, when he came on as controller for the Americas. In 1997 he was promoted to vice president and Worldwide Sales controller and then to corporate controller.




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