“Are you serious?”
I was about to ask R. James Woolsey Jr. that question before catching myself. He was always serious when the subject was national security. We will come back to that question.
Woolsey, director of Central Intelligence from 1993 to 1995, died on July 21, at the age of 84. The many tributes that followed rightly celebrated an extraordinary career in public service. They recounted his service to presidents of both political parties, his work in intelligence, diplomacy, arms control, energy security, and his lifelong contribution to the defense of the United States.
All of that deserves remembrance.
Yet public office alone does not explain a life. Offices are held. Principles endure.
I first met Woolsey during my earliest experience in government service. Neither of us could have imagined that what began as a professional acquaintance would become more than two decades of conversations, interviews, emails, telephone calls, collaborative writing, and friendship.
We were never the sort of friends who watched football together on a Sunday afternoon. Our friendship rested on something different: a shared interest in history, strategy, and the enduring questions surrounding the security of the American Republic.
Looking back, I realize those conversations shaped my own thinking more than Woolsey probably knew.
One of our earliest discussions occurred while I was researching what became my first book, “Crusading Realism.” We were discussing the strategic landscape after the collapse of the Soviet Union when Woolsey repeated an observation he had first made publicly in 1993.
“We have slain a large dragon, but we now live in a jungle filled with a bewildering variety of poisonous snakes. And in many ways, the dragon was easier to keep track of.”
I have quoted those words countless times over the years because they captured an enduring truth. The Cold War had ended, but history had not. The threats confronting the United States would become more numerous, more diffuse, and often more difficult to recognize.
Terrorism, rogue regimes, cyber warfare, revisionist powers, and emerging technologies replaced a single, identifiable adversary. Woolsey understood that before many others did.
He thought in decades rather than election cycles. He looked for enduring patterns rather than temporary headlines. That was one of the qualities I admired most about him.
I saw that same quality during a lunch we shared in Chicago.
Woolsey recalled attending a White House meeting following the events that became known as Black Hawk Down. As he remembered it, the discussion quickly centered on public relations—how the administration should explain events to the American people.
Finally, Woolsey interrupted.
“What are we going to do about the situation on the ground in Somalia?”
Silence.
Woolsey smiled as he described the room. It reminded him of a high school football team standing beneath the stadium lights after a difficult loss. Everyone stared upward. No one wanted to meet anyone else’s eyes.
Later, someone suggested Somalia might become a democracy.
Woolsey interrupted again.
“What are you talking about? This is a country run by violent clans.”
Again, silence.
Again, according to Woolsey’s recollection, the discussion returned to public relations.
I leaned back and asked him, “Are you serious?”
He looked at me with that slight smile I came to know so well and answered simply,
“Yes.”
That story remained with me because it explained Woolsey better than any résumé ever could.
He always began with reality.
Not politics.
Not messaging.
Reality.
Over the years, I came to understand that this was not simply Woolsey’s approach to Somalia. It was his philosophy of statesmanship. Strategy begins by understanding the world as it actually exists, not as we wish it to exist.
One of the conversations I remember most vividly took place while we were discussing what became our joint Washington Times article on the Obama administration, Iran, and the constitutional treaty process. The immediate subject was the administration’s handling of the Iran nuclear agreement, but, as was often the case with Woolsey, the conversation quickly moved beyond the issue of the day.
He was interested in the larger strategic consequences. Woolsey never believed Iran’s revolutionary character had fundamentally changed or that diplomatic agreements alone could transform its long-term ambitions.
Looking at events in the Middle East today, I cannot help but think back to that conversation. Woolsey was not attempting to predict headlines. He was identifying enduring strategic realities.
The same was true of Russia. Even as much of Washington shifted its strategic attention toward China, Woolsey repeatedly warned against allowing Russia to become yesterday’s problem. He believed Moscow remained a determined revisionist power whose ambitions had not diminished simply because public attention had shifted elsewhere. On this point, history has been remarkably kind to Woolsey’s judgment.
One of our last communications came only a month before Woolsey’s passing. We were discussing a new project related to spacepower. Woolsey was someone whose curiosity remained undiminished. He was still asking questions, still exploring new strategic frontiers, and still thinking about where the next challenge to American national security might emerge. Retirement had never become intellectual retirement.
Years earlier, when I interviewed him about the newly established United States Space Force, he immediately looked beyond satellites and launch vehicles toward the larger strategic implications.
“As long as we’re number one and can—with whatever combination we have of aerial vehicles, space satellites, other planets, whatever combination we have control over—that gives us control of unexpected parts of space and space follow-on.”
That answer was quintessential Woolsey. He instinctively thought strategically before he thought bureaucratically or technologically. His mind always gravitated toward the larger implications.
The public will rightly remember Woolsey as director of Central Intelligence.
I remember the man.
I remember his quiet smile and his dry sense of humor, often delivered with such understatement that you had to pay attention to catch it. Despite occupying one of the highest offices in the United States government, he carried himself without pretension. There was no need to remind anyone who he had been. His ideas spoke for themselves.
I remember how generous he was with his time. No conversation ever felt rushed. No sincere question was dismissed. He challenged assumptions, recommended books, drew upon history, and expected those around him to think seriously because the issues themselves were serious.
There was also something reassuring about Woolsey. He possessed a quiet confidence born not of arrogance but of preparation. He had done the reading, wrestled with history, and thought deeply about the strategic problems confronting the nation. You always left a conversation feeling you had learned something.
Like every consequential public servant, Woolsey accumulated admirers and critics alike. That is inevitable for anyone who spends a lifetime making difficult strategic judgments. Whether one agreed with every position he took ultimately misses the larger point. He never tailored his conclusions to the political fashion of the day. He followed history, evidence, and strategic logic wherever they led.
As I write these words, I cannot help but think of another generation now rapidly passing from the scene. I was privileged to know several remarkable men shaped by the Cold War, among them Ambassador James Lilley, Peter Pry, and Woolsey.
They often disagreed, sometimes vigorously, yet they shared an understanding that public service was a vocation, not merely a profession; that history remained the indispensable teacher of strategy; and that preserving the American Republic required both wisdom and strength.
America will continue to produce intelligence officers, diplomats, generals, professors, and public officials.
Whether it continues to produce statesmen like Woolsey is a far more consequential question. He was important to America; his death saddened me; it should sadden Americans.
Woolsey once observed that after slaying the dragon, we entered a jungle filled with poisonous snakes. More than three decades later, that observation seems even more relevant than when he first made it. He spent a lifetime helping America recognize the difference.
That is how I will remember him.
