Osama wrote hundreds of memos, letters and video messages containing explicit and detailed orders for his lieutenants, along with personal, security-obsessed missives for his family members, declassified files obtained by ABC News show.
"Bin Laden was very hands on with al Qaeda's day-to-day operations but he seemed somewhat out of touch," a senior US intelligence official familiar with the documents commented.
Bin Laden himself explained how it worked in letters such as one in early 2011 to one of his wives, seeking her advice on how to exploit the news media to hype the triumph of the upcoming tenth anniversary of the 9/11 attacks.
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"I will also ask for the brother to buy SIM cards that you can use to communicate with me and your messages. What you write and tell me in terms of ideas, I will include in the statements," bin Laden told her.
"Of course you know how important they are and how we need to exploit [9/11] in the media as the embodiment of the victories of Muslims."
For years, former President George W. Bush and his advisers spoke of bin Laden as "hiding in a cave" and dodging missiles from CIA drones.
One senior Bush administration official said in a 2004 speech that bin Laden "spends most of his time trying to figure out how 'they're going to come for me' and 'is this going to be the day?'"
While most of the tranche of files found at his hideout in Pakistan have not yet been cleared for public release, officials said most of the massive archive from hard drives and hard copies curiously are dated after 2009.
The documents also reveal that as far back as the mid- 2000s there were fears from some in al Qaeda that some in the group's Iraq franchise were attempting to split from the "core" organisation based in Pakistan.
Years later, those concerns would prove prescient as al Qaeda-Iraq (AQI) evolved into ISIS and publicly turned on its parent group, the report said.