Donald Rumsfeld was a complicated man. A two-time Secretary of Defense and a brilliant leader of Searle, he was an impressive man. While he was well-known as a Congressman and high-level government official, he became famous as the architect of the second Iraq war and the invasion of Afghanistan. 

I met Rumsfeld, who died earlier this week, a few times between his CEO days and government service when he was a senior partner at William Blair, a Chicago investment firm. His office was in the LaSalle Bank Building, as was mine. On occasion, I would arrive at the elevators for the upper floors just when he did. The 39 floors from the lobby to his office seemed like an eternity. 

Rumsfeld had a stare that made you think he was judging you, even if he was not. When he had a subordinate with him, the scene was different. He had no qualms about providing very direct feedback to these young men and women about their performance at the recently concluded business lunch.

These chance meetings were enough to make me curious about who he really was. One of my board members at the time knew him as head of the Office of Economic Opportunity during the Nixon Administration, where he created a name for himself as a rather liberal Republican. Another acquaintance remembered the fact that Rumsfeld, as a young Congressman from Illinois, had been co-sponsor of the Freedom of Information Act. A third person, a tough Democrat operative from Chicago, described him as the smartest Republican in the House. Hearing these stories made our vertical commutes together somewhat easier and his “mentoring” of junior staff started to make more sense.

Years later, I met Rumsfeld at a NATO Summit. Much to my surprise, he remembered me from those elevator rides, our infrequent interactions at the Attic Club on the top of our building, and various sessions at the Chicago Council on Foreign Relations. He was polite for a bit, then laid into me for a session that we had done at a side conference to the Summit. I have been criticized more sharply by many others, but the sharpness of his look left a mark on me for many years.

Don Rumsfeld was part of a generation of leaders who had acquired their chops the hard way: by serving in the military even if they went to Princeton. Yes, he had an Ivy League degree, but he also had the stuff of a tough, Midwesterner who could throw a punch when it was necessary. His tough-guy persona was real, but so was his sincere belief in government transparency and real compassion for the poor. 

My fleeting interactions with him over 30 years were enough to give me a sense that he was a special person filled with commitment and not afraid to be wrong. Let us remember him for, and try to emulate him in, that commitment and fearlessness.