I shared my own Brennan-humility story. Brennan retired in 1990. I was a third year law student at the time. I sent the Justice a copy of the ABA Journal, featuring his photo on the cover, and asked if he would autograph it for me. Brennan complied, along with sending a note saying that he was "flattered that [I] should want it." Yeah, that's humility. I showed the letter to Chertoff and it brought a smile to his face. He told me he still has the letters Brennan sent him on the birth of his children.

Latham & Watkins And The Visit To Death Row

Even before entering the profession Chertoff was experiencing things few others had. He was in Scott Turow's section at Harvard Law School. Chertoff doesn't need to read One L. He lived it! He shared with me a story of a debate over property rights that spanned two classes. Chertoff was at the center of it. The story made its way into Turow's legendary memoir of the school's grueling first year.

Following his clerkship Chertoff made the not uncommon pivot to Big Law -- taking a position at Latham & Watkins where he handled a variety of litigation as well as death penalty appellate work.

The firm represented three death row inmates in Arkansas, successfully having their death sentences overturned. A young Associate Chertoff visited the Cummins Unit Prison in Grady, Arkansas, to meet with a death row client. The gravity of it lingers in the air as Chertoff recounted the trip and how unusual it was. . [I couldn't help thinking: "Toto, I've a feeling we're not in Cambridge anymore."]

But Chertoff's time doing criminal defense work would be short-lived. The U.S. Attorney's office was in his sights. In 1983 he joined the office for the Southern District of New York. At the time, Rudy Giuliani was at the helm and the future New York Mayor was focused of organized crime. This led to Chertoff serving as lead prosecutor in the famed Mafia Commission Trial, which brought down the heads of New York's five crime families. Following a three month trial, the eight defendants were convicted on all 151 counts for all manner of RICO and extortion charges. The bosses received 100 year prison sentences. Chertoff went on to serve as the U.S. Attorney for the District of New Jersey, taking over from would-be Supreme Court Justice Samuel Alito.

While Chertoff would return to his old firm a decade later for a seven-year stint, doing white collar criminal defense work, his career trajectory was clearly public service.

September 11th And The Patriot Act

Chertoff had just started the head of the criminal division for the Department of Justice when September 11th hit. He described having one of those "big old car phones" and learning from his Deputy that planes had hit the World Trade Center. Chertoff headed to the Robert Mueller-headed FBI office. One the way he learned about the plane crashing to the Pentagon.

He was now in the thick of it, being "present watching on a video conference as the order was transmitted to shoot down the fourth plane." Chertoff said he remembers thinking "I never thought I would live to actually see something like this outside a move." After that, "the whole day was about figuring out who did it, who was on the plane, who were the hijackers and then what's going to happen next. We went into overdrive."

Just six weeks after the terrorist attacks, President Bush signed the "Uniting and Strengthening America by Providing Appropriate Tools Required to Intercept and Obstruct Terrorism Act of 2001" into law. The so-called Patriot Act was designed to give the government greater authority in tracking and intercepting communications.

Chertoff was involved in its drafting, offering the perspective from the Attorney General's Office. At the time, the nation was still shell-shocked and fear over the possibility of another attack was wide-spread. I suggested to Chertoff that, under such circumstances, any security provisions, possibility preventing a repeat, would have been passed. Perhaps, he told me. But was quick to explain that Attorney General Ashcroft did not "want to push the envelope and take advantage." Instead he wanted to "pick things that we've talked about for years that we think are important to do, get the technology updated to what's going on in the internet age [and] avoid the seams and lines that prevent us from sharing information."

May It Please The Court

In 2003 Chertoff, with aspirations to be a judge, began nearly two years of service on the Third Circuit Court of Appeals. His aspiration was to be a judge. It was "now or never," he told me. So after a career trying cases, Chertoff found himself facing the other direction in the courtroom.

It was a wholly different experience. "A way to be contemplative," he explained, "after the frenetic behavior over the last year and a half with trying to deal with constant threats." And boy was it ever. Chertoff good-naturedly recounted being asked by the Clerk's office if he could handle an emergency matter. Sure he said. "I'll stay as late as you need." But he was confused. They were checking his availability in case something came up in the next few weeks. "I thought 'wow this is a different [situation] … from you've got 20 minutes before something blows up and you've gotta stop it.'"
But Chertoff still yearned for action and wanted every case assigned to him to be argued. The more experienced judges, he explained, needed to quell his enthusiasm for the courtroom, pointing out that not every case needed to argued. "Well, let's not go wild here," they cautioned. Chertoff soon came around to seeing what they meant.

The President's Cabinet

Chertoff said he was content with the life of an appellate judge. But, in 2003, the call from the White House came. Chertoff was tapped to serve as President George W. Bush's Secretary of the Department of Homeland Security. Chertoff had 218,000 employees under him. If DHS were a city, it would be just about the hundredth largest in the country. Frenetic was back.

DHS is a massive organization. Is it just too big?, I wonder. Chertoff needed less than a second to say "no." The concept of having centralization of security related functions "makes a lot of sense."

But what about FEMA? What does disaster response have to do with keeping the bad guys out of the country? But that also makes sense, Chertoff said: "To really do security you've got to do response too." Not to mention, he explained, FEMA does not have a lot of assets. So it benefits from the ability to use the assets of the Coast Guard and Customs and Border Protection in rescues.
Chertoff headed DHS during Hurricane Katrina and has taken criticism for FEMA's response to the handling of it. Is that hard to hear? "You learn you have to take criticism," Chertoff told me. "I will say that when we started down the road to Katrina the rule was that state and local government are the first responders and the federal government supports. I don't think they ever had a circumstance where the Mayor was just holed-up in a hotel room and didn't do anything and the Governor was checked out too. They didn't order the National Guard and they didn't have a plan to evacuate people. So all of a sudden it was dropped in our lap with about a day to figure out what to do." But despite this explanation, Chertoff said he "understands politics and it was an opportunity to take shots at Bush. And it was probably ill-advised for him to take that picture in the plane."

Chertoff took the opportunity to say that the Coast Guard rescued 30,000 people – "a huge accomplishment." He also pointed out that the handling of the Katrina response led to creating a plan and capability for future hurricane response.

Exploding Data: Cyber, Privacy, Data And The Loss Of Autonomy

These days Chertoff's focus is risk management and cyber security. He heads the near ten year old Chertoff Group, which provides a host of services in the area. For example, Chertoff explained that this includes advising companies in the financial and utility sector on "what are the cyber and physical risks. Since you can't cut yourself off from the cyber space if you are a commercial enterprise, how do you organize your strategy to secure your key assets in such a way that allows you to conduct business. But that doesn't open the portal to people getting into the things that could fatally damage the business."

Four Star General Michael Hayden, former Director of the CIA and former head of the National Security Agency, has his office down the hall. I walked past legendary CIA man Charles Allen's office. There is some serious business going on here. Indeed, they know their security. My effort to steal the cool visitor badge, for a souvenir, was unsuccessful. I was nabbed at the front desk. I had to settle for a pen from the jar in the waiting room. Not the same.

As the former head of DHS Chertoff naturally has a wealth of knowledge on the subject. That Chertoff wrote a book about it is not surprising. But his recently published Exploding Data - Reclaiming Our Cyber Security In The Digital Age is much more than the tale of lost privacy that we experience on account of sharing so much of our personal data.

As Chertoff described it, our fear, of George Orwell's 1984 coming true, has been realized. But not for the reasons we anticipated. We worried that Big Brother "might force his way into our home," Chertoff said. But that's not necessary. "We are currently rolling out the red carpet to welcome him."

In Exploding Data, Chertoff takes a more unique approach to the subject. That our sharing of personal data has led to a loss of privacy is too narrow of a description of the risks we face. "That ship has sailed," Chertoff told me.

What is now at stake is a loss of autonomy. "What we should care about," Chertoff cautioned, "is when people use the data for a purpose other than what we intended. . . . At some point the data can be used to really manipulate or even coerce you." "Soft totalitarianism," he called it.

Chertoff shared an actual story of someone going through a divorce and emailing with their lawyer. On account of the right of the email provider to monitor emails, in an automated fashion, the soon-to-be divorcee began receiving ads for a dating site. "Wow!," Chertoff said. "If when I was in the government, I had, without a warrant, monitored email traffic between someone and their lawyer, I'd be in jail. . . . That was one of the stories that made me think people don't really understand what's at stake with the data."

But isn't this just the price of using all of this wonderful new technology?, I suggested. No, Chertoff replied: "If I want to use your data for a purpose other than the original purpose, I have to ask your permission. Maybe I have to pay you for it. If I'm going to make money using your data, which is the new gold, maybe you should be compensated for it. But you should have a right to say 'yes' or 'no.'" Chertoff offered one possible solution. "Maybe a service you get, if you are not willing to let them use the data, they'll say 'then were going to charge you a fee,' like a pay wall with a newspaper. The point is to give people a real choice and not simply force them to surrender what turns out to be the most valuable thing they have."