Last Thursday, over a reasonably priced eighty-five-dollar sea bass at a quiet, wood-paneled table in Georgetown, a senior State Department official turned to me and let out a long, weary sigh. We had been discussing the intractability of the global south, as one does when the Pinot Grigio is flowing and the burdens of empire weigh heavily on the shoulders of the American administrative state. The topic, inevitably, had drifted toward Havana. My dining companion placed his silver fork down onto the crisp white tablecloth, looked me dead in the eye, and asked a question that has haunted me ever since: How can Cubans move forward if they aren’t ready to reckon with their past?
It is a profound and necessary question. For over six decades, the United States has generously provided the island nation with a rich, vibrant tapestry of historical events. We have invested billions of dollars into shaping their national destiny, occasionally via direct amphibious assault, but more often through the thoughtful, quiet application of crippling economic strangulation. Yet, instead of expressing gratitude for this bespoke historical narrative that Washington has painstakingly curated for them, the Cuban people remain stubbornly fixated on their own subjective version of reality. They cling to their grievances. They refuse to let go of the past. And frankly, I am losing my patience.
As anyone who has spent time in the Acela corridor knows, diplomacy requires a shared set of facts. But how can we negotiate in good faith with a population that simply refuses to acknowledge the history we have written for them? Take, for example, the events of April 1961. To the American foreign policy establishment, the Bay of Pigs was merely an unsolicited amphibious feedback session. It was a well-intentioned, albeit poorly executed, attempt at rapid regime restructuring—a classic case of Washington trying to help a neighbor tidy up their domestic affairs. But if you talk to a Cuban on the streets of Havana today, they will dramatically reframe this standard administrative maneuver as a "hostile invasion" by a "foreign imperial power." It is this exact sort of histrionic, victim-mentality rhetoric that prevents the island from healing.
This pathological refusal to reckon with our version of their history extends to the economic realm as well. The United States embargo against Cuba—el bloqueo, as the locals melodramatically insist on calling it—is now in its sixty-third year. It is one of the most enduring, stable, and reliable pieces of foreign policy in modern American history. When President John F. Kennedy signed the initial proclamation in 1962, he famously secured 1,200 Petit Upmann cigars for his own personal humidor just hours before making the trade restrictions the law of the land. As a columnist, I look at that anecdote and I see the charming, rugged pragmatism of the American executive branch. I see a leader who understands the delicate balance between geopolitical necessity and the appreciation of a quality Connecticut shade wrapper.
But the Cubans? They completely miss the humor in it. Instead of chuckling at Kennedy's elite hustle, they stubbornly point to the subsequent six decades of rolling blackouts, crumbling infrastructure, and severe shortages of basic medical supplies. They wave empty antibiotic bottles in the air as if a lack of penicillin somehow invalidates the broader theoretical goals of the Helms-Burton Act. It is this exact lack of perspective that makes them so difficult to work with. They are so bogged down in the minutiae of their own material suffering that they completely fail to appreciate the elegant, bipartisan legislative framework that is causing it.
We must also address the elephant in the room: the CIA's colorful history of covert operations. Throughout the 1960s, the Central Intelligence Agency engaged in a series of highly creative, out-of-the-box brainstorming exercises aimed at facilitating a change in Cuban leadership. Operation Mongoose was a golden age of American geopolitical whimsy. We explored putting thallium salts in Fidel Castro's shoes to make his beard fall out. We experimented with poisoned diving suits. We even investigated the feasibility of a spectacularly rigged exploding cigar.
In any healthy relationship, you have to be able to look back at your early, awkward years and laugh. I wore a velvet blazer to a White House press dinner in 1998; the CIA tried to hire the Chicago mob to poison a head of state. We all made mistakes in the twentieth century. We were experimenting. We were finding ourselves. But instead of viewing these hundreds of documented assassination attempts as the quirky, James Bond-esque historical trivia they so clearly are, the Cuban government insists on treating them as "acts of state-sponsored terrorism." How are we supposed to build a bridge to the future when they insist on bringing up every little exploding mollusk we left in their territorial waters fifty years ago?
This is why Washington's current efforts to help Cuba rewrite its history are so vital, and why I fully support my friends at the State Department in this endeavor. We are simply asking the Cuban people to adopt a more productive, pro-market view of their own timeline. We want them to look past the embargo, past the sanctions, and past the covert regime change programs, and focus on the positive aspects of our shared heritage. Why can't they focus on the 1950s? Under the Batista regime, Havana was a thriving, vibrant playground for American mobsters like Meyer Lansky. We offered them a dynamic, service-based economy centered almost entirely around fetching highballs for men named "Bugsy" and turning a blind eye to offshore casino skimming. It was a beautiful, symbiotic relationship. They threw it all away for literacy programs and universal healthcare, and they have been demanding we apologize for it ever since.
It is deeply frustrating to offer a nation a beautifully drafted, fully finalized version of their own timeline, only to have them stubbornly point to the material reality of their daily lives.
Vance is exactly right, and his tireless work in the bureau deserves a Presidential Medal of Freedom. We have handed the Cuban people a meticulously crafted narrative in which they are the irrational actors, and we are the patient, benevolent superpower just waiting for them to come to their senses. All they have to do is accept it. All they have to do is look in the mirror, reckon with the fact that they forced us to strangle their economy for three generations, and apologize.
It is really not that big of an ask. We are not asking them to give up their sovereignty—well, not entirely. We are simply asking them to voluntarily subject their domestic economy to the whims of American capital, dismantle their state institutions, and politely ignore the Title III lawsuits waiting to repossess their homes on behalf of the descendants of Bacardi executives. In exchange, we will graciously allow them to purchase our grain at a markup, provided they pay in cash up front, since they are still locked out of the international banking system. It is a win-win scenario, drawn up by the finest minds at our top think tanks.
Yet, the stubbornness persists. Every time Washington extends an olive branch—usually in the form of a heavily redacted intelligence report detailing how we plan to fund their domestic opposition groups—Havana slaps it away. They demand "respect" and "sovereignty," buzzwords that sound nice in a United Nations General Assembly speech but have absolutely no place in a mature, adult conversation about the Western Hemisphere's geopolitical reality.
I am not an unreasonable man. I consider myself a pragmatist. I am willing to meet the Cuban people halfway. I am willing to concede that the Platt Amendment, which legally enshrined our right to intervene in their country whenever we felt like it, may have been slightly heavy-handed by today's standards. I am willing to admit that the ongoing occupation of Guantanamo Bay is perhaps a minor zoning dispute. But this reconciliation must be a two-way street.
If the Cuban people want a future—if they want to finally emerge from the shadow of the past and embrace the bright, shining promise of foreign direct investment and unregulated luxury condo developments—they must take the first step. They must look deep within themselves, reckon with the history Washington has so generously written for them, and ask for our forgiveness. Until that day comes, I will continue to order the sea bass, enjoy my Pinot Grigio, and shake my head at the tragic, self-inflicted wounds of a people who simply refuse to listen to reason.