Exclusive—Michael Dulak: Reframing the 9/11 ‘Failure of Imagination’ 25 Years Later

Today, as I join fellow service members, civilians, and senior leaders in the Pentagon Center Courtyard for the 25th Anniversary 9/11 Pentagon Observance Ceremony hosted by the Secretary of War, we will gather to pray, remember, reflect, and honor the victims and heroic first responders of that tragic day. Yet, as we stand on this hallowed ground a quarter-century later, remembrance must be coupled with renewed vigilance.

The most important finding of the 9/11 Commission remains our most urgent warning: our greatest vulnerability was not a shortage of raw intelligence, but a profound “failure of imagination.” What America witnessed that fateful morning demonstrated once again how our enemies will exploit the boundaries of our conventional thinking—operating freely within the sanctuary of the unthinkable.

To secure our nation for the next 250 years, counterintelligence (CI) must adopt a new commandment: Never underestimate the audacity of our enemies. We must overcome our cognitive blind spots, reject the illusion of shared logic, and actively anticipate how our open society’s legal and civic frameworks can be weaponized against us.

A New Commandment for Counterintelligence

Former CIA Chief of Counterintelligence James Olson codified the “Ten Commandments of Counterintelligence” in his seminal book, To Catch a Spy. His directives—such as “Be Offensive,” “Know Your History,” and “Never Give Up”—are foundational doctrine for CI agents navigating the “wilderness of mirrors.” They are irrefutable, forged from hard-won victories and devastating losses. Yet, an eleventh commandment is required for the modern era: Never Underestimate the Audacity of the Enemy.

The sky glows orange as the sun rises over the damaged side of the Pentagon with the U.S. Capitol behind it in Washington, DC, on September 13, 2001, days after a hijacked airplane crashed into the Pentagon. (LUKE FRAZZA/AFP via Getty Images)

Our adversaries target national defense information with predictable constancy. Today, the homeland is a contested environment. The frontline is no longer just a battlefield overseas; it is in the Pentagon, at every U.S. military installation, and in the direct messages and social media feeds of every service member, civilian, and contractor. Foreign adversaries are using sophisticated online targeting and social engineering to extract data, feed media leaks, and spark unauthorized disclosures.

As adversaries weaponize our open society, we must build upon Olson’s teachings. While we are trained to follow a strict orthodoxy of verification to avoid paralyzing paranoia, we are repeatedly blindsided. This is not due to a lack of data, but a profound cognitive blind spot: we simply cannot believe the enemy would go that far.

The Historical Cost of Cognitive Blindness

A failure of imagination—the inability to conceive of an unprecedented threat—has repeatedly altered American history. For CI professionals, underestimating the enemy’s audacity is a mortal sin.

In 1941, U.S. intelligence officials failed to detect Japanese consulate-based espionage operations in Honolulu which contributed valuable intelligence to the planning and execution of the surprise attack against Pearl Harbor.

Similarly, U.S. counterintelligence during the Manhattan Project suffered a catastrophic failure of imagination by focusing strictly on Axis infiltrators rather than anticipating that a wartime ally would recruit atomic spies. Consequently, ideologically motivated physicists like Klaus Fuchs and Theodore Hall easily bypassed security frameworks undetected because officials could not conceive that brilliant, idealistic scientists would willingly compromise atomic secrets.

Fast forward to February 2001, the U.S. counterintelligence community discovered that FBI Special Agent Robert Hanssen had spent two decades exploiting fundamental flaws in the Bureau’s security architecture. The FBI’s internal trust system was built on an assumption that proved catastrophic: it could not conceive that one of its own counterintelligence officers would betray the United States to Russia and the former Soviet Union for pure financial greed.

Seven months later, the devastating attacks of September 11, 2001, occurred. The official 9/11 Commission Report explicitly identified a collective “failure of imagination” and a breakdown in interagency communication. While critical intelligence existed, we failed to envision that Al-Qaeda terrorists would exploit U.S. flight schools to weaponize commercial aircraft as guided missiles to strike the symbols of American military and economic power.

The Illusion of Shared Logic

Our most dangerous vulnerability is “mirror-imaging”—the assumption that the enemy’s risk calculus mirrors our own. We implicitly rely on Western norms to constrain our thinking, asking if an operation is too resource-intensive or difficult.

But our adversaries do not play by our rules. By assuming they will act “reasonably,” we create a sanctuary of the unthinkable. The enemy operates precisely within this sanctuary, exploiting the gaps where our logic dictates an action is too risky or brazen to attempt.

Weaponizing the Open Society: The Long Game

Our adversaries view the legal and civic frameworks of our open society as attack surfaces.

Consider the potential to penetrate our defenses through the strategic weaponization of U.S. military naturalization. Under Executive Order 13269, non-citizens serving in the armed forces during designated conflicts are eligible for expedited naturalization. For those with no ill intent, this rightly rewards honorable service. To an adversary, it is a glaring vulnerability. CI must imagine the audacity of a foreign intelligence service deliberately dispatching a trained operative to enlist, rapidly acquire citizenship, secure a security clearance, and manufacture a well-placed spy or saboteur.

Even more chilling is the prospect of the generational sleeper agent. The Supreme Court recently reaffirmed that children born in the United States to parents temporarily or unlawfully present are citizens at birth under the Fourteenth Amendment. For foreign intelligence services, this is a constitutionally protected charter for long-term infiltration.

Imagine a pregnant proxy of a foreign intelligence service arriving to give birth on U.S. soil. The child—a U.S. citizen—is immediately relocated abroad to be raised and indoctrinated. Two decades later, holding an unassailable U.S. passport and possessing no derogatory database footprint, they return to attend a U.S. university, obtain a STEM degree, and enter the defense industrial base or the intelligence community. This is the logical extension of a committed adversary willing to patiently weaponize our Constitution against us over decades.

First responders who were on the scene of the September 11, 2001 terrorist attack on the Pentagon salute above a large U.S. flag draped on the side of the Pentagon during a memorial ceremony on September 11 2006, in Washington DC. (MANDEL NGAN/AFP via Getty Images)

The Cognitive Shift

To counter this asymmetry, CI professionals must treat “improbable” scenarios as actionable hypotheses. If an operation seems too complex or long-term for the enemy to execute, it must immediately be elevated as a viable threat vector.

Complacency and hubris are the ultimate allies of audacity. When a nation believes its perimeters are impenetrable and its laws immune to weaponization, it ceases to look for the unconventional threat. We must actively imagine the worst possible scenario—because our adversaries are already busy planning it.

Michael Dulak is the Director of Counterintelligence & Identity Intelligence in the Office of the Under Secretary of War for Intelligence & Security. He has over four decades of counterintelligence experience. The views expressed in this article are solely those of the author and do not reflect the official policy or position of any government agency.