Reuters and ABC Television were given exclusive access to the documents, which were translated from Arabic and declassified by U.S. intelligence agencies.
They were part of a second tranche of documents seized in the operation and have been declassified since May 2015. A large number have yet to be released.
One document, a hand-written note that U.S. intelligence officials believe the Saudi militant composed in the late 1990s, laid out how he wanted to distribute about $29 million he had in Sudan.
One percent of the $29 million, bin Laden wrote, should go to Mahfouz Ould al-Walid, a senior al Qaeda militant who used the nom de guerre Abu Hafs al Mauritani.
"By the way, he (al-Walid) has already received 20,000-30,000 dollars from it, bin Laden continued. "I promised him that I would reward him if he took it out of the (Sudanese) government."
Bin Laden lived in Sudan for five years as an official guest until he was asked to leave in May 1996 by the then-Islamic fundamentalist government under pressure from the United States.
Another 1 percent of the sum should be given to a second associate, Engineer Abu Ibrahim al-Iraqi Sa'ad, for helping set up bin Laden's first company in Sudan, Wadi al-Aqiq Co, the document said.
Bin Laden urged his close relatives to use the rest of the funds to support holy war.
"I hope for my brothers, sisters and maternal aunts to obey my will and to spend all the money that I have left in Sudan on jihad, for the sake of Allah," he wrote.
He set down specific amounts in Saudi riyals and gold that should be apportioned between his mother, a son, a daughter, an uncle, and his uncle's children and maternal aunts.
In a letter dated Aug. 15, 2008, and addressed "To my Precious Father," bin Laden asks that his wife and children be taken care of in the event he died first.
It was unclear to whom bin Laden was writing, as his natural father, Mohammed bin Laden, died in a 1967 airplane crash. U.S. intelligence officials were not immediately available to comment on whether he may have been referring to his step-father, Mohammad al-Attas.
"My precious father: I entrust you well for my wife and children, and that you will always ask about them and follow up on their whereabouts and help them in their marriages and needs," he wrote.
In a final wistful paragraph, he asks for forgiveness "if I have done what you did not like."
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