The first time Adis Medunjanin tried to call Robert C. Gottlieb in mid-2009, Gottlieb was out of the office. Medunjanin was agitated. He had to speak to an attorney. Gottlieb’s assistant told him Gottlieb would be back soon. When Medunjanin spoke to the lawyer a little later, he was told he might need legal representation. He thought he might be under investigation.

Over the next six months and in forty-two phone calls, Medunjanin sought legal advice from Gottlieb. When he was arrested in January 2010 on charges that he tried to bomb the New York subway, it was Gottlieb who defended him, receiving security clearance to review government documents pertinent to the case in the process.

Gottlieb was preparing Medunjanin’s defense when a federal officer in charge of information distribution e-mailed him that there was new classified information he needed to review at the US Eastern District Court in Brooklyn. “I went over to the Brooklyn Federal courthouse, went up to the secured room, gained entry with the secret security codes, opened the file cabinet that is also secure and in the second drawer was a CD,” Gottlieb told me. On that CD were recordings of every single one of his forty-two phone calls with Medunjanin before he was taken into custody and indicted on January 7, 2010.

Such calls are normally sacrosanct under the principle of attorney-client privilege, the ability to speak confidentially with your lawyer. But a leak to The Guardian last summer of National Security Agency (NSA) procedures that are supposed to protect privileged calls showed that some attorney-client privileged calls are not subject to internal rules that detail the instances when a wiretap should be turned off. A later version of the procedures declassified by the NSA last August contains the same language.

These “minimization” procedures, as they are known, are the rules and regulations for wiretaps under the Foreign Intelligence Surveillance Act (FISA). They tell NSA agents when they can listen, and when they have to turn the tap off, when they can record and when they should not be recording. There are rules for which kinds of communications can be monitored—for example, domestic communications are off limits, although communications from agents of foreign powers and suspected terrorists don’t count as domestic—and there is a section that provides for the protection of attorney-client calls.

Section four of the declassified 2011 guidelines is the part of that document that governs wiretapping attorney-client calls. At first glance, it seems quite clear: when the agent realizes that he or she is monitoring an attorney-client communication, “monitoring of that communication will cease and the communication will be identified as an attorney-client communication in a log maintained for that purpose.”

But given a second reading, section four doesn’t apply to all attorney-client calls. It provides only for the minimization (and protection) of the calls of “a person who is known to be under criminal indictment in the United States”—someone who has already been charged under US law. This is because indicted persons have a Sixth Amendment right to counsel. People who aren’t indicted don’t have this right, and so their calls are not minimized. When I asked an NSA press officer, Vanee’ M. Vines, how attorney-client privilege was protected, she referred me to the Department of Justice. I left several messages, but the DOJ never contacted me back.

“The invocation of National Security trumps other rules,” Joshua Dratel, a veteran New York lawyer who has litigated over thirty terrorism cases told me over the telephone. Dratel says that calls subject to attorney-client privilege are not covered by the NSA’s minimization.

“These are calls that are covered by the privilege that are not covered by that kind of minimization,” he added. “FISA is 24/7, there’s no real minimization; in a practical sense it doesn’t exist. In all the FISA cases I’ve legislated, I’ve had no minimization.”

* * *

Attorney-client privilege is often called one of the most “ancient” principles of US law, and lawyers view it as one of the most sacred. “It’s one of the oldest principles underlying our system of justice,” says Ellen Yaroshefsky, the director of the Jacob Burns Center for Ethics in the Practice of Law at Cardozo School of Law in New York City. “Without it you can’t allow a lawyer to do their job in providing their client with adequate and serious representation.”

Alexander Abdo, a lawyer with the American Civil Liberties Union (ACLU), insisted in a telephone interview that the bond between lawyer and client had to be protected. “It really comes down to trust—clients need to trust their lawyers. If they can’t trust their lawyers, they can’t do their job,” he said.

There are exceptions to the rule. Attorney-client communications may be monitored in the case that authorities believe the attorney and client are engaging in crime or fraud. Lawyers doing dirty work for mob bosses were famously wiretapped in the 1990s. More recently, a FISA warrant was used to reveal that Lynne Stewart, a human rights lawyer, was passing messages on behalf of a client convicted of terrorism. In 2005, a court found she was doing so in violation of special administrative measures (SAMs) imposed by court order upon her client and sentenced her to twenty-eight months in prison. In 2010, an appeals court ruled that her previous sentence was too light and resentenced Stewart to another ten years.

Under a standard Title III wiretap, used in domestic cases, minimization must be used on all privileged calls—pre- and post-indictment—unless there is the suspicion of criminal activity. Non-pertinent information should also be minimized—and destroyed. But as Marjorie Cohn, a former president of the National Lawyers Guild and a professor at the Thomas Jefferson School of Law in San Diego, told me, even this stipulation is stretched by federal agencies. “As long as it’s reasonable not to minimize, they don’t have to minimize.”

That said, defenders of the policies argue that wiretaps can be an essential tool to catch terrorists. Najibullah Zazi, the man who fronted the subway-bombing plot that involved Medunjanin, was caught because his emails to handlers in Pakistan were intercepted by federal agents. Norm Abrams, an emeritus professor of law at the University of California, Los Angeles told me that it was a complicated balancing act. “I think that it’s important to give Government special tools,” he said. “But we don’t want to lose our civil liberties.”

* * *

I met Robert Gottlieb early on a September morning in his office in the Trinity Building in Downtown Manhattan. He has grey combed-over hair and explains things slowly and in detail, like a patient schoolmaster. Among the legal certificates and degrees on his walls hangs a picture of Abraham Lincoln and a poster from his unsuccessful 1985 campaign for District Attorney of Suffolk County that reads: “Bob Gottlieb convicted international terrorists. No one in Suffolk County is going to push him around.”

He still doesn’t know why he was given access to the wiretaps of his supposedly privileged calls. The prosecution certainly didn’t deem them pertinent to the case, and although they were declassified, they were never presented at Medunjanin’s trial. Gottlieb listened to every single one of the recordings at the Brooklyn court. He was shocked.

“I listened to call after call holding my breath to see and to hear what I said in these conversations. It turned out that I was very careful and very circumspect,” he said, but he was angry that his privilege had been violated and that the law, as he saw it, had been ignored. The judge denied Gottlieb’s request that the government disclose its application to the FISA court for a wire-tapping warrant. “Everybody is harmed when government ignores law because that weakens the foundation of law that ultimately must and should be applied fairly and strictly in every situation to every individual. So if you are willing to chip away and to weaken the law when it suits your governmental purpose, then everyone in the future is victimized by government violations of law.”

Gottlieb isn’t the only attorney defending suspects involved in the 2009 subway plots who was wiretapped. Lawyer Ron Kuby defended Ahmad Wais Afzali, an imam who was tried for providing material support to the subway plotters. He told me over the telephone how he learned he was wiretapped for the entire first day of communications with his client. And though he was never told under what authority he had been listened to and recorded, he explained, “the only act that would authorize it is the act that must not be named”—FISA.

Kuby was asked to come to the Joint Terrorism Task Force’s headquarters in Chelsea (“this really cool office in this really hip neighborhood,” as he described it, with only a hint of sarcasm in his voice). After a wait, he was called upstairs to a conference room, and the tapes of three conversations with his client were played back to him with law enforcement agents sitting in the room. He still doesn’t know why this happened, because the tapes were—as in Gottlieb’s case—never introduced as evidence.

Afzali had called Kuby for legal advice. All the time, he was being listened to by government agents.

“The DOJ’s guidelines are so fucking narrow that they apply only to those who have been indicted,” said Kuby. “Since he was not indicted, they did more than just listen. Saturday morning we agreed that we would have a press conference on Sunday. The FBI chose to preëmpt that conference by arresting him on Saturday evening.”

“It’s beyond concern,” he added, “This is ongoing legal advice in an incredibly volatile situation in which the DOJ has a big stake, but they just didn’t give a fuck.”

* * *

A case that is often cited when people talk about attorneys who’ve been wiretapped is the Al Haramain case. In August 2004, attorneys Wendell Belew and Asim Ghafoor—lawyers for the Saudi charity Al Haramain—were presented with evidence by the Treasury Department, which was leading the investigation, that calls with their client were being wiretapped under the Bush government’s warrantless Terrorist Surveillance Program (a program now officially discontinued, and discreet from FISA). “It was not the usual kind of information we were used to getting from the Treasury,” Belew told me over the telephone. And while he continues to be bound by court order not to disclose the documents’ details, it was widely reported in the media at the time that the agency involved was the NSA.

“We were not allowed to use the documents themselves,” Belew said of the civil case Al Haramain later brought against the US government. “The government took back copies of those documents from everybody who had them,” and the court eventually dismissed the case.

The Bush program ended in 2007, after a public and press outcry. A year later, the FISA Amendments Act of 2008 expanded the executive ability to wiretap and granted retroactive immunity to the telephone companies that participated in the warrantless wiretapping program. Critics like Daniel Ellsberg, the Pentagon Papers whistleblower, rallied against the act, saying that without the ability to bring civil suits against the private telephone companies, citizens would not be able to find out what the government was doing. But lawyers continued to believe their communications with clients were once again immune to government snooping. FISA court oversight, it was assumed, would protect privileged conversation.

But so little has been disclosed that it’s difficult to have public oversight, and so little information has made its way before a judge. “It’s not an area where there’s much recent law,” said Norm Abrams, the UCLA law professor. “We don’t have any court decisions.” He explained, for instance, that FISA doesn’t mention the attorney-client privilege.

But complications arise because most attorneys—notwithstanding being presented with evidence that they had been tapped like Kuby and Gottlieb—would never know, and may never even suspect they had been recorded. For example, Reuters revealed that the Drug Enforcement Administration was using information gleaned from NSA wiretaps to prosecute drug dealers. They then used a technique known as “parallel construction” (a frequently employed technique in law enforcement) to use other evidence in the investigation to scrub any mention that the wiretap took place. As one former DEA agent told the journalists, “It’s just like laundering money—you work it backwards to make it clean.”

* * *

The day the FISA Amendments Act was ratified, a case was brought by Amnesty International (in which The Nation and its contributing journalists Naomi Klein and Chris Hedges were plaintiffs) that asserted, among other things, that wiretapping was being used in all kinds of situations where conversations should have been privileged. The suit was dismissed earlier this year.

Alexander Abdo, one of the ACLU lawyers on the case said it is hard to litigate on cases where lawyers have been wiretapped because the government refuses to acknowledge the taps. “It’s very difficult to prove that it’s happened and it’s very difficult to get them to admit in court that it’s happened,” he added. He said wiretapping was a legitimate fear, and attorneys have changed their practices to meet the needs of an era where the government might be listening to their every call.

And it isn’t just people involved in the ACLU case who are concerned. Dratel, the terrorism lawyer, confirmed that he and his colleagues had changed their communication strategies. They now use encryptions and turn their cellphones off at meetings. “We’re taking all these precautions which ten, fifteen years ago would have seemed suspicious. Now they’re part of a legitimate fear and way of doing business,” Dratel told me. “It’s like some Ocean’s 12 film.”

That may all be changing now in the wake of Snowden’s revelations. At the end of October, the Justice Department notified a defendant for the first time that information being used against them at trial came from warrantless wiretaps, and legislation was introduced that would make judicial oversight and debate on State wiretapping more feasible. Senator Ron Wyden—who did not want to comment directly on the attorney-client issue—told me that new bipartisan legislation he had worked on would allow people to challenge wiretaps in court. “The Supreme Court’s Amnesty v. Clapper ruling made it nearly impossible for law-abiding Americans to prove that they have standing in federal court to challenge secret government surveillance,” he explained in an e-mailed statement.

* * *

Another case, ACLU v. Clapper, was filed last summer after a document leak that showed Verizon metadata were being logged by the NSA and focuses on metadata, which can contain information covered by attorney-client privilege. Metadata do not contain the content of calls or other electronic interactions; they are merely the information that a communication existed, where it originated and at what time it took place. But Patrick Toomey, one of the ACLU staff lawyers on the case, said that the records that the calls even existed were covered by the attorney-client privilege.

“One of the many revealing things metadata can convey is the context of calls based simply on who calls the ACLU and where they’re calling from,” Toomey told me over the telephone. “This is the equivalent of privileged data.”

Where the law stands on this and other issues of attorney-client privileged speech is complicated, partly because it’s not a subject that has been legislated upon. What is privileged and what is not? Where does the privilege apply, and where can it be protected? Are intelligence officials law enforcement officers or something else entirely?

Norm Abrams, the UCLA professor, told me “the law isn’t simple” on whether the information conveyed by targeted metadata collection is privileged. On the other hand, he did not believe that the mass collection of metadata—simply the storing of such information in a database with millions of other e-mail traces—violated privilege. And while he would welcome more legislation by Congress, he didn’t think that a House as divided as the current one would be able to pass any such legislation.

I asked him what he thought the reaction of the government would be if such a case did make it to the courts or in Congress. “I think the government would probably make an argument that they could do things under FISA which they couldn’t do otherwise,” he said. “Given the fact that FISA modifies the otherwise applicable Fourth Amendment rules—the argument that FISA may also overcome the Fourth Amendment and attorney-client privilege, it’s not implausible.”

Cohn, the Thomas Jefferson Law professor, insisted that any type of government surveillance on such privileged communications is a violation of the law. “The attorney-client privilege,” she added, applies “any time a client is consulting an attorney as an attorney.”

Robert Gottlieb also takes a strong line on the issue. Less than a year after his client had been convicted, the memory of the case, and the illegal wiretap still animated him. Outside his office, the bells of Trinity Church pealed through the bright, blue September morning. For Gottlieb there is no confusion and no debate. The government, he said, must not violate the attorney-client privilege.

“The time that we really test ourselves to see whether we really believe in this country’s principles arises in the most serious cases and if you can’t protect the constitutional rights and the sacred principles that underlie our entire system of law in serious case then it is in danger, even in minor cases, depending on the whim of the officials who are in power. That’s not the way this country was formed to operate,” he said, tapping the table. “The only thing that should be done is that government should be told in no uncertain terms by the courts, by Congress that you may not violate the attorney-client privilege. End of story.”