Former federal prosecutor Eric Friedberg conducted the first court-approved email wiretap nearly 20 years ago while investigating an international conspiracy to sell fraudulent cellphones.
"It was entirely novel. Even email was new," he says. "CompuServe, the provider, had no way to comply. They had to build a new port."
But today, Friedberg, an Internet intelligence pioneer who describes himself as "extremely pro-law enforcement," is among a growing number of former national security and law enforcement officials who are questioning the current scope of the National Security Agency's data-gathering programs.
"There's a legitimate public policy debate about whether it's worth a societal cost of having a permanent record of every person's telephone calls for a long time in a single place," says Friedberg, who grapples with this. Sometimes, he says, people's freedom "is protected by the difficulty that law enforcement has in obtaining records. If they can look at anything at the push of a button, abuses are more possible."
Last June, a series of news reports based on classified documents provided by former NSA contractor Edward Snowden began documenting government surveillance programs that included spying on friendly foreign leaders, analyzing email and Internet use, and gathering phone records of millions of Americans.
The disclosures triggered protests, congressional hearings and dozens of recommendations to limit broad sweeps of data. Last week, President Barack Obama adopted some of those, calling for an end to government control over vast amounts of phone data. Instead, Obama said, the telephone service providers or a third party should keep the bulk records, "with government accessing information as needed."
But he didn't go nearly as far as a consortium of former NSA staffers and intelligence agents had recommended in their own January letter to Obama asking him to dramatically limit government surveillance.
One of those former staffers, Thomas Drake, says it is a "heavy burden" to have broken new ground with digital-surveillance software and techniques decades ago only to see those tools now being used to collect email, Internet use, credit card and cellphone data from innocent Americans as part of a system he considers unconstitutional.
"I wake up at night in a cold sweat just thinking about what's been unleashed," he says.
Drake was part of a team in the late 1990s that developed a system to collect and analyze billions of electronic records to identify potential terrorist plots. But unlike current practices, he says, the system created back then would have kept U.S. citizens' data private through encryption that could be unscrambled only with a judicial order.
The system was never used, he says. Instead, the NSA adopted a more invasive intelligence-gathering program, much of which became public knowledge through Snowden's leaks.
In their recommendations, the former spooks urge the administration to have the Foreign Intelligence Surveillance Court, which oversees the NSA's secret surveillance programs, make all its rulings public. They also want to outlaw secret searches and see effective whistle-blower protections for national security employees.
Obama said that some FISA rulings are being declassified and that some additional restrictions will be imposed on what can be searched. With regard to whistle-blowers, however, Obama said individuals who publicly disclose classified information may endanger the nation.
Drake, who started working for the NSA as a contractor in 1989 and a staffer 2001, disclosed an electronic espionage program that he saw as invasive in 2002. He was indicted under the Espionage Act, but the felony charges were dropped before trial. He was found guilty in 2011 on a lesser charge and sentenced to a year of probation and community service.
Another team member, William Binney, who left the NSA with Drake, has no remorse about his 30 years of intelligence work and technological advances at the agency. He blames officials for overstepping the bounds.
"I don't feel bad about it," he says. "The technology side was something I had to work on in order to solve foreign threats. That's like saying you would never have invented the pistol because it might be used to kill people."
By no means are all former intelligence agents troubled - or taken aback - by the recent disclosures.
"Anything that surprised me? No, not really," Tim Sample, a former CIA analyst who worked on Capitol Hill with the House Permanent Select Committee on Intelligence, says with a laugh.
"I am very confident and comfortable with the fact that everything has been done within a legal framework that was approved by the executive branch, the legislative branch and the judicial branch."
And even Friedberg, who was at the forefront so many years ago with that first email content grab, follows up on his misgivings about privacy with concerns about security: "On the other hand, given the heightened need to try to prevent terrorist attacks - instead of reacting to them after they succeed - it may be necessary to conduct these very broad data collections to enhance intelligence agencies' ability to connect the dots in advance of the bad guys acting."