Glenn Gerstell will be the first to tell you that he has enjoyed exceptionally fortunate timing throughout his career. But as he reflects on almost four decades of wide-ranging accomplishments at Milbank, and his current role as General Counsel of the National Security Agency (NSA), it’s clear that Glenn has always had a talent for anticipating trends – and preparing himself for challenges – in order to end up in the right place at the right time. Glenn Gerstell retired from Milbank in 2015. For current information see his website.
Quoting hockey great Wayne Gretzky, Glenn observes that one of Milbank’s strengths as a firm has always been to “skate to where the puck is going to be, not where it has been.”
This foresight has been a defining theme of Glenn’s career as well, and at the NSA, he has taken on a role that is a culmination of his expertise, including law firm management, international experience, and a deep background in telecoms and technology.
As a young lawyer joining Milbank in 1976, Glenn was inspired by Milbank partners like statesman John McCloy and former Attorney General Elliot Richardson, whose exceptional careers mixed private practice and public service. “I always knew that I wanted to have some involvement in government in some way, but I also wanted to get a solid grounding in becoming a good lawyer with a traditional Wall Street practice,” he says. Early in his career, he got that grounding in Bankruptcy, which gave him a valuable perspective on how people and businesses react to and handle crisis situations, before moving on to a wide range of transactional work.
From Washington to Asia
As a 4th-year associate, Glenn was asked to move to the firm’s new Washington office, where he had an “extraordinary opportunity” to work with, and learn from, the firm’s newest partner at the time, Elliot Richardson – with whom he eventually argued a successful case before the U.S. Supreme Court, a highlight of Glenn’s career.
As the business world became increasingly globalized, Glenn found himself skating ahead of the puck as he was tapped to go to Milbank’s new Singapore, then Hong Kong, offices just as the Asian “tiger economies” began taking off. In the late 1980s and early 1990s, demand for the firm throughout Asia was incredibly high. Glenn recalls: “This was a remarkable time; there was an explosion of work in all areas. We had clients literally pleading with us to take their work.”
Around this time, Asia also began experiencing the privatization wave in telecoms that had already swept through the U.S. with the breakup of “Ma Bell.” “The World Bank went around the region encouraging Indonesia, Thailand, Malaysia, and others to unlock the tremendous value in what, for many countries, was their biggest asset: the telephone company,” Glenn says. As a result, “country after country turned their telephone company into a private sector vehicle with lots of legal work flowing from that,” and Milbank was at the forefront of this trend. Returning to Washington as a partner, after eight years in Asia, Glenn then brought this experience to the Latin American countries beginning to ride their own telecom privatization wave, including the privatization of Brazil’s giant Telebras in 1998.
Glenn reflects that his Milbank experience was enhanced along the way by his work with mentors such as Richardson as well as Judge William Webster and Frank Musselman, who inspired his own management style. “Frank used to have a saying that there are two ways to get things done: One is to be really nice and the other is to be really nasty. And then he’d pause for a second and add with a grin, ‘And they both work.’ Obviously I have chosen the former; Frank was a real master at getting people to do his bidding in a nice way. You never realized you were doing his bidding; you just did it because it seemed like the right thing to do. That is good leadership.”
Bringing his leadership experience to a legal team at the NSA that serves a global agency of more than 40,000 people, Glenn has taken on one of the more challenging and complex positions in government service. He joined the NSA in mid-2015 immediately following his retirement from Milbank – moving directly into a spy agency that is at the heart of an intense public conversation about counter-terrorism, individual privacy rights, and surveillance practices. Glenn notes that “because the Agency regards adherence to the law as an absolute foundation stone of everything it does, the General Counsel’s position is an important and prominent one. So I have the honor and responsibility of working directly with not only the Agency’s Director but also Congress, the White House staff, and the heads of other intelligence agencies.”
The NSA has two broad missions, foreign intelligence and information security, including cyber-security. The latter is becoming increasingly important, Glenn observes, as it can relate to everything from protecting the Department of Defense’s global network to the President’s nuclear command communications systems. While it’s no surprise that questions concerning the legalities of security and intelligence gathering regularly come across his desk, the General Counsel also handles all of the other issues that arise in an organization of this size, including massive government contracts, human resources, real estate, litigation, patents, and more.
Mission-Driven
While the NSA’s legal office differs greatly from a corporate law firm – it is essentially a military organization, with strict hierarchies – it also employs a very high caliber
of professionals, Glenn says. Perhaps defying stereotypes about government employees, “There is a tremendous level of technical expertise here,” he notes.
“At this agency, everyone is mission-driven; they truly want to be here. They probably could be making lots more money working at Facebook or Microsoft, but they’re here because they believe they are doing something important – and they are.” Teamwork is essential for getting things done, he adds, which reminds him of the collaborative approach of his colleagues at Milbank.
“I’m incredibly lucky to have had a rich, rewarding Milbank career for 39 years and then to get to follow up with another equally fascinating opportunity to do public service,” Glenn says. “The NSA operates at the intersection of two of the most significant things the federal government is doing today: counter-terrorism and cyber-security.
It’s just a terrific opportunity, and an incredible privilege and honor to be here.”
