He has been a guest at the White House, served as one of the CIA's chief assets in its war against the Soviets in Afghanistan and was once referred to by Congressman Charlie Wilson as "goodness personified."
But today, Jalaluddin Haqqani presides over the most defiant insurgent network threatening Afghanistan.
Blamed for Tuesday's audacious assault on the U.S. embassy in Kabul, and a surge of similarly spectacular attacks, the Haqqani network has emerged as the most potent and unpredictable force in the decade-long war in Afghanistan.
"They are expanding their frontiers. They run purely on intimidation and violence," said Matthew DuPee, an Afghan security specialist at the Naval Postgraduate School in Monterey, Calif.
"They are going to be the primary threat for the foreseeable future. … Kabul will be a primary target."
The Haqqani network is a group of roughly 3,000 fighters based out of North Waziristan in Pakistan and three of Afghanistan's eastern provinces. Al-Qaeda's connection to the insurgency in Afghanistan is found within its ranks in the form of a small number of fighters.
Although they represent a small slice of the insurgency, their Iraq-style attacks on high-profile targets such as the U.S. embassy have transformed the nature of the conflict.
They have been implicated in practically all of the recent brazen assaults in Kabul. They have claimed responsibility for attacks on India's embassy, bolstering assertions that they act as an agent of Pakistani interests, which in turn protect them.
Mr. Haqqani, a revered mujahadeen commander during the U.S.-backed war against the Soviets, is now elderly, frail and thought to be suffering from lupus based on a noticeable tremor in his last videotaped address broadcast in 2008.
Hailing from a Pashtun tribe from Paktia province, he has carved out a sanctuary for himself in North Waziristan, where he lives in a sprawling mansion, regularly attends the local mosque and oversees a trucking and warehouse business, as well as cross-border smuggling operations.
The United States has targeted the Haqqani base with failed drone strikes while increasing pressure on Pakistan to crack down on the family. But besides the arrest of Nasruddin Haqqani – a minor figure – in December of last year, the family has enjoyed relative immunity from Pakistani security forces, elements of which reportedly view them as a way of wielding influence in Kabul in any kind of political settlement to the conflict. Pakistan has denied supporting the Haqqanis.
Even when he was younger, Mr. Haqqani held multiple allegiances. While on the CIA payroll, he is reported to have helped protect Osama bin Laden, who at the time was mustering his own forces to overthrow the Soviets.
Mr. Haqqani allied himself with the Taliban just before the movement swept to power in Kabul, serving as both a military commander and minister in the Taliban government.
After the U.S.-led invasion of Afghanistan, Mr. Haqqani rejected an offer from President Hamid Karzai to serve as his prime minister and at one point topped the CIA's 'hit list' along with Mr. bin Laden.
He withdrew to North Waziristan, where he expanded his network, recruiting from the ranks of Afghan refugees and Pakistani madrassas in the tribal regions.
As Mr. Haqqani's health fails, it is understood that he has transferred command of the network's military operations to his son, Sirajjudin, who is in his mid- to late-30s and is considered more of a hard-line Islamist than his father.
"The son has picked up right where the father left off," Mr. DuPee said.
The Haqqani network's original goal – to regain full control over its traditional bases in Khost, Paktia and Paktika provinces – has morphed into something more ambitious, analysts say.
In part, they've leveraged the diminishing influence of the Taliban's Quetta Shura to assert a broader claim on Afghanistan. And while the Taliban has softened its tone in recent years – asserting, for instance, that girls should be allowed to go to school – in an attempt to win loyalty among Afghans, the Haqqanis rule by fear.
"Their pool of fighters has stayed the same for years, but they are trying to assert their control in much bolder ways," Mr. DuPee explained.
Their attacks have become signature: A breach of a security perimeter by insurgents disguised as security forces, or as women, followed by the storming of a high-profile target.
Formally at least, they identify as part of the Taliban movement. They are loyal to its spiritual leader Mullah Omar. When they issue a statement, the Haqqanis use letterhead embossed with "The Islamic Emirate of Afghanistan," further indicating an alliance with the Taliban.
But the prospect of a peace deal with the Taliban has caused Afghan and Western leaders to overstate the distinction between the two.
Ryan Crocker, the U.S. ambassador to Afghanistan, on Wednesday played down the attack on his embassy, shifting the blame away from the Taliban who have claimed responsibility for the attack.
"The information available to us is that these attackers [are]part of the Haqqani network; they enjoy safe haven in northern Waziristan," Mr. Crocker told reporters in Kabul.
Mr. DuPee says such a distinction does not reflect the reality that the Haqqanis' influence is growing within the Taliban movement.
"There's an acute attempt [on the part of Western and Afghan officials]to separate this group from the Taliban proper, which they want to engage, because the prospect of peace with a movement that included the Haqannis would be too unpalatable for everyone," he said.