"Bin Laden has to feel as though things are beginning to close in on him," said Cloonan, who has been in touch with people who have met bin Laden in the past. "I believe that he knows that his days as the iconic leader of the Jihad movement are really numbered."
"Anytime we have a successful strike like this, his paranoid has to increase," said Cloonan of bin Laden. "The number of people he trusts will shrink even more and there will be a lot of chit chat among jihadists, particularly in that region, about where the system broke down and who gave up information about Mehsud."
There had been a $5 million bounty on Mehsud. There is a $25 million price on bin Laden's head.
The lethal drones will continue to roam over Pakistan's skies in search of their next targets, and some names are already getting penciled in on their "to-do" list.
Already, possibilities for Mehsud's successor -- and possible targets for the drones -- have been identified:
Hakimullah Mehsud, one of Mehsud's deputies and the head of the Taliban in Khyber, Kurram and Orakzai agencies.
Wali ur-Rehman, who has helped control access to Mehsud and acted as a messenger between the Taliban chief and his deputy commanders along the Afghanistan-Pakistan border.
The strike on Mehsud may also have an effect on others considering assuming leadership of jihadist movements.
But among the people who may be vying for the most left empty by Mehsud's killing are individuals who are likely to question whether they want to put themselves at risk, said Cloonan.
"When you take out the head of the Taliban in Pakistan there is going to be a succession battle," he said.
"But some of these warlords are going to start thinking to themselves, 'Am I next?'" said Cloonan. "Even if we think from our side that these people aren't human, at the end of the day there are some people there who really don't want to die."
To locate those people and begin negotiations with them in an effort to gather information about bin Laden and the Afghan Taliban would be a huge feat, according to Cloonan.
"We have to force these people into some sort of negotiation process because we cannot, it's impossible, for us to take out every leader of the Taliban," he said.
"We ought to drive a wedge between them," Cloonan said of the rising Taliban leaders in Pakistan. "Ultimately the game is to work out some sort of agreement that would be the worst thing for bin Laden."
ABC News Nick Schifrin in Pakistan contributed to this report