"Nobody really knew who these were going to, why they were being produced, what the real driver was - other than they were what Kevin wants us to work on," said one former employee.
Company records and interviews show Chalker consulted with and received advice on some of his proposals from then-CIA employee Denis Mandich, who worked as an agency liaison to Silicon Valley.
Those projects included a multibillion-dollar proposal in 2014 to have Global Risk Advisors invest in tech startups on Qatar's behalf, pitched as a way to block the sale of potentially sensitive technology to its Persian Gulf rivals.
It's unclear from company documents if that project moved forward and Mandich later left the agency and joined Global Risk Advisors to become one of Chalker's top lieutenants. Mandich's attorneys did not respond to questions about his work for GRA.
Global Risk Advisors also created a detailed security plan in 2014 to install a surveillance system in Qatar that could track mobile phones in the country "with extreme accuracy" and allow analysts to "isolate individual conversations and listen in real-time," according to internal company records that include a draft contract.
Project Berlin
That plan, dubbed Project Berlin, also suggested creating a World Cup 2022 mobile phone app that could record users' location and movements.
Chalker indicated in internal company documents that Qatar gave preliminary approval to Project Berlin but it's unknown whether it was ever implemented.
Chalker's efforts at boosting Qatar's ties with the US included an effort to set up a face-to-face meeting between top officials at the CIA and Qatar's prime minister.
One Qatari official told Chalker that such a meeting help would provide a "golden stamp of approval" for Chalker's various projects, company records show.
But those records show Chalker's initial efforts to broker such a meeting failed despite his boasting of having unparalleled access to the highest levels of the Qatari government.
The CIA declined to comment.
Other company records showed Global Risk Advisors pushed to have oversight and control of Qatar's US lobbying efforts, saying it could manage those efforts more productively.
A March 2017 proposal called "Project ENDGAME" said Qatar's enemies were seeking to inject the country into proxy fights involving its "allies" such as the Muslim Brotherhood, an Islamist group backed by Qatar.
In response to that threat, the company boasted in internal records that it had "developed an approach to a close contact of the congressman" who sponsored legislation that year to designate the Muslim Brotherhood as a terrorist organization. "Developed an approach" is intelligence jargon for seeking to recruit a potential asset.
Dominate the information battlefield
That congressman, Florida Republican Rep. Mario Diaz-Balart, said he was unaware of such efforts and that he's continued to sponsor similar legislation in the years since.
"The allegations that a former CIA officer is actively trying to influence an important national security bill on behalf of a foreign country are deeply disturbing," Diaz-Balart told AP.
The "Project ENDGAME" proposal also warned that President Donald Trump was "unpredictable" and his inner circle was being co-opted by the UAE's well-connected ambassador in Washington, Yousef Al-Otaiba.
The proposal suggested Qatar obtain "total information awareness" into Otaiba and his US allies and then spread damaging information through friendly media outlets.
"Now is the time to once again seize the initiative to dominate the information battlefield," the proposal said.
In April 2017, Chalker and a Qatari government official signed a letter of intent that said Global Risk Advisors would provide Qatar with "enhanced tracking and monitoring, intelligence collection, predictive intelligence, information operations" and other spy services for $60 million over three years. Other records show a Gibraltar-based company owned by Chalker began receiving seven- and eight-figure payments from Qatar shortly afterwards.
No direct evidence
Anonymous hackers began leaking selectively curated copies of Otaiba's emails in June 2017. Those emails included potentially embarrassing messages showing Otaiba's close relationships with top US officials and significant influence at some think tanks.
There's no direct evidence linking Global Risk Advisors to the release of Otaiba's emails. Chalker has categorically denied playing any role in a hack-and-leak operation, and no former Chalker associates who spoke with the AP said they saw the company engage in such activities.
The hackers' targets in the Otaiba leaks included a former Defense secretary, former high-ranking diplomats and intelligence officials, and two think tanks that had been critical of Qatar and were specifically named in the "Project Endgame" pitch document.
Hacked emails
After going dormant for several months, the hackers released a new round of Otaiba emails in 2018 focused on Tom Barrack, a close Trump adviser who is currently on trial for allegedly working illegally for the UAE and whose hacked-and-leaked emails form part of the Justice Department's case.
Former Trump fundraiser Elliott Broidy has accused Chalker and Global Risk Advisors in an ongoing lawsuit of overseeing the Otaiba hack and leak on Qatar's behalf as well as a similar operation targeting Broidy that began in early 2018. Chalker's lawyers have called the lawsuit "baseless."
Chalker associates say he has shifted his focus away from Global Risk Advisors in recent years to a quantum computing cybersecurity company he formed with Mandich called Qrpyt, which has signed a technology licensing agreement with the Department of Energy's Oak Ridge National Laboratory.
-Suderman reported from Richmond, Virginia. Investigative reporter James LaPorta in Wilmington, North Carolina, contributed to this report.