The Value of Planning Ahead

I'm curious as to why Osama didn't take the Assange route and tuck away some incriminating documents concerning his job history at the CIA somewhere, ordering someone to release them should he ever be caught or killed.
Even if we did capture him and put him on trial, its not like we'd do any but the most superficial of trials, sort of like the one Saddam got that was cut off before they could get to his complicity and work for the US government.

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