Excerpts from documents apparently seized from the Saudi-born jihadi's residence in Abbottabad, Pakistan, where he was killed by US special forces in May 2011, suggest a man somewhat different from the stereotype of a pitiless terrorist leader.
They show someone willing to forsake an Islamic state in Egypt -- surely one of his cherished aims -- if the price was the welfare of the population.
In one of the 17 documents released by the US-based Combating Terrorism Center (CTC), Bin Laden cites the challenges facing Egypt's would-be Islamist rulers.
"Before building a Muslim state, the Islamic Group [Gamaa Islameya] could have thought about food security for the Egyptian people," it is claimed Bin Laden wrote in one memo, referring to the Islamist organisation involved in the assassination of former president Anwar Al-Sadat.
The group had the stated aim of establishing an Islamic state in Egypt and planned to seize control of government buildings, institutions and media outlets. But the Al-Qaeda leader claims their plans overlooked vital issues related to Egypt's economy and food supply.
"If God had willed for the Islamic state to be born in Egypt, it would have not probably lasted more than a few weeks," wrote Bin Laden, explaining that international sanctions would have led to starvation due to the country's then reliance on American wheat.
At that time, Egyptians relied on 150 million loaves of bread per day, Bin Laden claimed.
"So, what would happen when Egypt could no longer import wheat from its major supplier, the United States?" he asked, adding that Egypt's wheat reserves were only enough for two weeks' worth of food and that its government had abandoned plans to make the country more self-sufficient.
"How long would the public tolerate having to go without [bread]?" he asked. "That has nothing to do with whether the public liked or disliked the Islamic state. A dangerous shortage of food causes death and people do not want to see their children die of hunger."
The US's release of these comments comes just weeks before Egypt's first post-Mubarak presidential elections. Islamists are among the top contenders, including leading light of the Muslim Brotherhood, Mohamed Mursi, and ex-Brotherhood member Abdel-Moneim Abul-Fotouh.
Bin Laden concluded that, unlike Somalia or Afghanistan, where people had humble needs and could depend on agriculture and livestock, Egypt could not survive the "unconventional weapon" of economic sanctions.
"The Afghan population is considered to be outside the modern-state system, and unlike Arab populations," he wrote.
In early May, the Combating Terrorism Center at the US's West Point Military Academy released 17 declassified documents captured during the Abbottabad raid the previous year.
They consist of electronic letters and draft letters authored by several Al-Qaeda figures, including Osama Bin Laden, and totalling 175 pages in the original Arabic.
The CTC website warns of possible problems with its English translations, and recommends the documents be read in the original language.
The earliest document is dated September 2006 and the latest April 2011.
The preface to CTC's study, published on its website, admits that in contrast to his public statements that focused on the injustice of those he believed to be the "enemies" of Muslims, namely "apostate" Muslim rulers and their Western "overseers", the focus of Bin Laden’s private letters is Muslim suffering at the hands of their jihadi "brothers".
He advises them to forswear domestic attacks that cause Muslim civilian casualties and focus on the United States, the "desired goal".
Bin Laden's frustration with regional jihadi groups and his seeming inability to exercise control over their actions and public statements is perhaps the most compelling story in the declassified papers.