CIA lawyer John Rizzo ’69 was in his office at headquarters in Langley, Virginia, on September 11, 2001, when word came that planes had struck the Pentagon and the World Trade Center towers. Another plane was said to be on its way to an as yet unknown target in Washington, perhaps Capitol Hill, the White House, or the CIA.

After an order went out to evacuate the CIA compound, Rizzo walked over to his top-floor wraparound windows and looked out on the parking lots. Hundreds of employees rushed to their cars. CIA headquarters is designed to be extremely difficult to enter. It’s not much easier to exit. The backup at the parking lot exits stretched far back. Rizzo figured it would take him hours to get out.

Instead, Rizzo chose to stay in his office. He watched the carnage unfolding in New York on his TV. Rizzo, who had been at the CIA for almost thirty years, sensed that everything was about to change in Washington, and that the CIA would likely play an aggressive role in rooting out whoever was responsible for these attacks and in making sure none would follow. Sitting at his desk with a yellow legal pad, he began writing down a legal framework for the agency’s role in capturing, detaining, and interrogating suspected terrorists. To what lengths could the CIA go, he wondered, without breaking the law?

“I was blue-skying,” Rizzo says. “How far could we push the envelope?” He thought about secret prisons, so-called “black sites” scattered around the world. He didn’t think the American public would accept the presence of terrorists in American jails, and the agency couldn’t just hand terrorists to other countries.

Some six months later, Rizzo learned about another way the CIA was responding to 9/11 that he says he could never have imagined. A group of agents gathered in his office wanted to employ “enhanced interrogation techniques,” or EITs—unusually harsh methods of extracting information from prisoners. The list included psychological humiliation, dousing naked prisoners with freezing water, insult slaps, blows to the abdomen, sleep deprivation, cramped confinement, stress positions, and even waterboarding. By this time, the entire national security apparatus of the U.S. government was focused on preventing the next major terrorist attack on American soil. “It was not if,” Rizzo recalls, “but when there would be another attack.”

As acting head of the Office of General Counsel, the top lawyer at the agency, it was up to Rizzo to decide if the EITs were permissible under American and international law. They sounded to him a lot like torture. But a month earlier alleged Al-Qaeda leader Abu Zubaydah had been arrested in Pakistan and brought to a secret prison. Agents in the field were convinced that he knew about a planned second attack on the United States. He refused to talk. CIA agents told Rizzo they couldn’t make any progress unless they were given authorization to employ EITs.

Rizzo had been through enough CIA scandals over the years to know this was bound to cause trouble. “I could have said, ‘This is too crazy, this is too risky. Prudence dictates we don’t even go down this road,’” he says. “And I could have made it stick.”

But Rizzo did not say that. Instead, after conducting his own research into the matter, he asked for an opinion from the U.S. Department of Justice. Eventually, the issue was picked up by Deputy Assistant Attorney General John Yoo, who, along with Assistant Attorney General Jay Bybee, wrote what would become loosely known as the “Torture Memos,” a series of legal opinions that set the legal limits for how far the CIA and the defense department could go in the interrogation and treatment of terrorist detainees. The memos offered detailed legal justification for most EITs.

One of these top-secret memos dealt specifically with the proposed interrogation of Zubaydah. “It appears you have conducted an extensive inquiry to ascertain what impact, if any, these procedures individually and as a course of conduct would have on Zubaydah,” Jay Bybee wrote in a letter addressed to Rizzo. “You have consulted with outside psychologists, completed a psychological assessment and reviewed the relevant literature on this topic. Based on this inquiry, you believe that the use of the procedures, including the waterboard  . . . would not result in prolonged mental harm. . . . Thus, we believe that the specific intent to inflict prolonged mental [harm] is not present, and consequently, there is no specific intent to inflict mental pain or suffering. Accordingly, we conclude that on the facts in this case the use of these methods separately or [as] a course of conduct would not violate Section 2340A [the U.S. legal code against torture].” The CIA now had the green light the agents were looking for.

One of Barack Obama’s first actions as president was to rescind by executive order all the justifications for torture contained in the Torture Memos. No one knows how history might have been changed had Rizzo told the agents who first approached him about the EITs that the techniques were illegal. There were already top-level officials in the Bush administration discussing the use of harsh interrogation techniques. But Rizzo still believes that he could have shut down the EIT program by telling the agents who came up with the proposal that it was illegal torture. “I had the experience, credibility, and influence to have made that call,” he later wrote.

Instead, Rizzo, a loyal CIA agent whose long career reflected his passion for and loyalty to the agency, ensured that his name would become permanently linked to enhanced interrogation, a link that would eventually end his career. “Mostly my conscience is clear,” Rizzo says today. “I’m content.”

Rizzo lives in an elegant townhouse in the Georgetown section of Washington, D.C. In the living room are a plush beige sofa, a softly ticking grandfather clock, and an Oriental rug. A sunroom is filled with plants. The odor of cigar smoke is notable, thanks to a smoking habit Rizzo picked up at Brown. These days he smokes three or four imported cigars a day.

At the agency, unknown to him, he earned the nickname “Beau Brummell” after the nineteenth-century British dandy. When I visit him, he’s dressed in a gray cashmere jacket with a white handkerchief; a striped, collarless dress shirt; and black loafers. “I enjoy clothes,” he says. “Sadly, they are the closest thing I have to a hobby.” A light white beard fringes Rizzo’s face. He is soft-spoken, congenial, and, even as we get into the nitty-gritty of EITs, he remains calm and relaxed. He says he’s an optimist: “I’m a glass-half-full kind of guy.”

In January, Rizzo published Company Man: Thirty Years of Controversy and Crisis in the CIA, a memoir about his agency career, which began in January 1976. He has witnessed every major CIA scandal since that year, from Iran-Contra and the outing of double agent Aldrich Ames to the intelligence failures behind 9/11 and the never-found weapons of mass destruction in Iraq. He concedes that Company Man, which the agency vetted, might give a reader the impression that “it was just one shitstorm after another.” Rizzo himself was an exemplary company man. He was never implicated in any of the tempests, and as a senior agency lawyer he was often called to investigate the day’s mess or to smooth over relations with an infuriated Congress.

Company Man contains no bombshells. It doesn’t seek to settle any scores. Instead, it is an honest, low-key telling of Rizzo’s behind-the-scenes role in bringing the CIA back from the brink and in making sure it complied with the country’s laws. Rizzo comes across as a dedicated civil servant who loved his job and held his colleagues in high regard. Up until the last few years of his career, it’s an amazing tale of political survival within an agency that has often operated on the legal margins, even occasionally overstepping them.

The reviews of Rizzo’s book were mostly favorable, though he was also criticized for going too easy on his former colleagues. About Ollie North, a central figure in the Iran-Contra scandal, Rizzo writes, “He was very smart and always willing to listen. His energy level was nothing short of phenomenal.” Rizzo is protective of George W. Bush, whom he believes never knew about EITs being deployed on prisoners, even though in Bush’s own memoir, Decision Points, the former president admits to authorizing EITs, which he defends. (The chain of communication, Rizzo claims, ended with Vice President Dick Cheney.) “Company Man falls short,” journalist Fred Kaplan wrote in the New York Times, “because Rizzo is so enamored with the agency, and so defensive about its critics, that he seems unaware of his own blind spots.”

In conversation, though, Rizzo is willing to admit to blind spots. He displays none of the hubris or self-righteousness that characterizes many former Bush administration officials who continue to defend the use of EITs. Rizzo argues that the EITs were legal and did not constitute torture, but he recognizes that it’s an issue on which reasonable people may disagree. When asked to justify his decision in favor of EITs, Rizzo says, “What if Abu Zubaydah said afterward, ‘See, I knew all about it [a second attack] and you guys couldn’t get me to tell you.’ Thousands of innocent people would be dead, and I would have known it was partly because I had scrubbed the whole idea.”

Rizzo also says that as general counsel his job was more narrowly focused than determining the morality of such techniques as waterboarding. “No one ever raised questions of morality,” he says. “The imperative for me as a lawyer was, first of all, is it legal? And if it was legal, how do I ensure that the agency was protected?”

Rizzo also emphasizes that waterboarding was hardly widespread. It was, he said, a method of last resort: “Keep in mind waterboarding was only done on three detainees, and we had over 100 prisoners. Torture is usually done on a more systematic basis. The three guys all seem to be in fine fettle [today]. I don’t think even some years removed that anyone subjected to waterboarding or even sleep deprivation has suffered any permanent physical or psychological damage.

“I’m reconciled to living with this for the rest of my life.”

Rizzo grew up middle-class in Worcester and then Wayland, Massachusetts. His father worked in a department store. In his book he describes his childhood as “very happy and very uneventful.” At Brown, he joined Beta Theta Pi. During pledge week, he was told to carry cigarettes around in his pocket, but his father smoked cigarettes and he’d developed a distaste for them, so he started smoking cigars instead. Beta Theta Pi members had a reputation for being wild, wealthy, and preppy. This is when Rizzo’s Beau Brummell began to emerge.

A political science major, Rizzo took a class with Professor Lyman Kirkpatrick, a former reporter for U.S. News & World Report, who became the inspector general and executive director of the CIA. Despite being wheelchair-bound due to polio-caused paralysis, he was a charismatic, imposing campus figure who inspired in Rizzo a desire to work in government. When Rizzo later applied to join the CIA, Kirkpatrick was the first person he thought of. “He had a subconscious influence on me,” Rizzo says.

Rizzo steered clear of politics, even when faced with the growing campus opposition to the Vietnam War. He says he just wasn’t interested, even though the war triggered his law school application. “In all honesty,” he says, “I applied to law school because I didn’t want to get drafted.” Rizzo was called for an induction physical anyway and was utterly surprised when he flunked it due to a kidney stone attack.

While in law school at George Washington University, Rizzo interned at corporate law firms, which he didn’t like. After graduation, he took a job at the U.S. Department of the Treasury but found it bureaucratic and boring. Around this time, Senator Frank Church began holding committee hearings after a 1974 New York Times article reported that the CIA had for years engaged in illicit and covert operations. Rizzo figured the agency might need some legal reinforcements, so he sent over his résumé. “It was a shot in the dark,” he says. The CIA had never needed many lawyers before because so few laws limited its operations. The Church Committee hearings changed this. The agency’s Office of General Counsel doubled in size from nine to eighteen lawyers, one of whom was Rizzo.

Rizzo loved his new job. The issues he was working on were momentous. “It’s like being admitted to this really exclusive club that no one on the outside can really understand,” he says. “It was cool.” He could tell his friends he was a lawyer at the CIA, but nothing more. Even with his wife he was forbidden to talk openly about his work. “You’re inside a bubble,” he says. The result is tight-knit camaraderie at the office, but sometimes at the expense of forgetting you are accountable to the public.

Rizzo owes much of his longevity at the agency to his ability to stay above the political fray. He saw himself as first and foremost a civil servant and attorney. He never registered as a member of either political party. He says he always voted for the incumbent in presidential elections. If the incumbent wasn’t running, he’d vote for the candidate from the incumbent’s party. The only exception was in 2008, when he voted for Obama over John McCain.

The affable Rizzo seems to have gotten along with everyone. The harshest criticism in his book is aimed at Bill Clinton, not because of his policies, but because he was disrespectful toward the CIA. When in January 1993 a Pakistani man shot and killed two CIA employees in their cars outside the Langley compound, Clinton sent Hillary to the scene rather than go himself. Rizzo writes that this was “the most hurtful snub I witnessed in my entire career.”

In all likelihood Rizzo would have spent the last years of his career as official head of the CIA’s legal office, instead of acting head, and would have retired from a long, successful, and widely admired career. Then along came Abu Zubaydah.

In March 2006, President Bush nominated Rizzo to become the CIA’s permanent general counsel, an appointment that requires Senate confirmation. On June 19, 2007, Rizzo testified before the Select Committee on Intelligence in a sober dark suit and bright yellow tie. His wife, Sharon; his son, James; and his sister, Nancy, sat behind him.

The senators pounded him with questions about his role in approving EITs. Did he think the enhanced interrogation techniques used by the CIA were humane, Michigan Senator Carl Levin asked him.

“Yes, sir,” Rizzo answered.

West Virginia Senator Jay Rockefeller asked whether Rizzo agreed with the Bush administration that torture occurred only when there was “serious physical injury such as organ failure, impairment of bodily function, or even death.”

“I did not, certainly, object,” Rizzo replied. His only objection, he later told the committee, was that he thought the administration had gone “overboard” in its acceptance of what constituted torture.

Near the end of the hearing, California Senator Dianne Feinstein made explicit what many of the senators thought privately. “I happen to have a very strong belief that the legal foundation on which torture was based was deeply flawed,” she said. “And I mean, if you were part of that legal foundation, it’s very difficult for me to vote for you.”

Over the next several weeks, Rizzo lobbied senators on the committee, but he clearly didn’t have the votes. He withdrew his nomination in late September. In retrospect, he says, “I was naïve. I thought I would not be politically controversial. I was not a political appointee. I was a lifer.”

Two years later, Rizzo retired. “How many of us,” he says, “know what the first paragraph of our obituaries is going to read? I know what mine is going to read.”

Lawrence Goodman is the BAM’s senior writer.