Gambler-in-Chief: The Declining Value of Strategy in Trump’s World

By Adin DobkinOctober 1, 2017

Gambler-in-Chief: The Declining Value of Strategy in Trump’s World

Gambling and War by Justin Conrad

JUSTIN CONRAD examines pigeons in the closing pages of his new book on military strategy, Gambling and War, and it somehow fits. The birds were at the center of a classic 1947 study by B. F. Skinner, in which pigeons were first starved and then fed at random intervals. They began to form superstitions: turning around in particular directions, tossing their heads in the same manner, or reaching toward a particular corner of the cage. In other words, they put meaning where none existed with the hope of bringing about a desired result. Their meaningless “strategy” for the sake of feeling good was presumably a comfort to their bird brains.

I read Gambling and War shortly after digging through digitized stacks of letters and memoranda from those who were there when World War III didn’t begin between the United States and the Soviet Union. This seems like the only meaningful, if entirely unsatisfying, way of describing the Cold War: by what it wasn’t. By what it almost became. Decades of peering over the edge — as if the premise of civilization itself jilted us — only to be pulled back by our better, cooler-headed halves.

A particular thread from the conflict kept pulling me back. It was a lesser-known story from the Cuban Missile Crisis — an event that’s been indelicately compared to the exchanges between President Trump and his young counterpart in the hermit kingdom of North Korea, with its threats of “fire and fury,” the state of being “locked and loaded,” and the blunt declaration that we are “on the brink of nuclear war.” Though I don’t agree with all the claims about the similarities between these two events, I still came back to those days in 1962 while reading present-day headlines. Not because of the details, but rather because the story I researched does away with one of our more persistent myths about wars and their making — one that Conrad demolishes over the course of Gambling and War.

The story followed a small group of Soviet submarines that floated in the Sargasso Sea, a featureless, gyrating body of water off the East Coast, while John F. Kennedy and Nikita Khrushchev postured in their respective corners of the globe. When Kennedy addressed the nation on October 22 and implemented the blockade of Cuba, he knew the submarines existed. He, or his advisors, even knew their approximate locations. What they didn’t know was that each submarine carried a single nuclear torpedo — its explosive power roughly equivalent to that of Little Boy dropped on Hiroshima 17 years before. And in all but one scenario, it was the captain of the submarine with the authority to launch that weapon.

Some days later, nearing a climax more appropriate for a Tom Clancy paperback than the deliberation over the starting date of a nuclear winter, one of the submarines was caught in a storm of depth charges. The charges didn’t have the power to destroy the sub, only signal it to come to the surface, but it matters little as that was information the submariners lacked. Over the preceding hours, carbon dioxide in the submarine had reached near-deadly levels due to a prolonged dive. The captain, Valentin Savitsky, saw two choices: he and his crew could quietly suffocate underwater, or he could follow his orders and go out with the proverbial guns blazing — after all, if the depth charges were any measure, war had already begun. Considering the circumstances, it’s not surprising that he gave the order to ready the torpedo for launch.

Then, war didn’t begin. The submarine held its fire.

We’re trained to first credit the heads of state. How, through reason and power, they saw humanity tipping over the edge and raced forward, grabbing our arm. If we’re generous, we might even give some credit to Captain Savitsky. Perhaps his mind’s eye looked back toward family and friends at home who would live, or die, with the repercussions of his actions. In more recent months, we’ve looked around at the tableaux that pop up with the prompting of cable news only to find an absence where that prescient guardian rests.

In the case of the Cuban Missile Crisis, Savitsky’s submarine had an extra passenger aboard, a higher up from the unit, who began a heated discussion with Savitsky after hearing the order. After some time, and with the input of the political officer aboard the ship, the captain’s decision was vetoed. Had that additional commander not been aboard Savitsky’s submarine, well, one’s mind wanders to 1,000 bleak presents.

There are a few reasons why, I believe, this story hasn’t entered our political canon. For one, we only learned about it some 50 years after it occurred. Most of the sailors who took part in it were gone and the world’s attention had shifted to newer threats with which it could whet its appetite for fear. Even in the best of circumstances, we have significant issues with understanding history. However, I couldn’t help but think there was a second reason why it never caught on. Instead of hinging upon heated hallway discussions with leaders and advisors, last-minute calculations from craniums in government labs, or even a comparatively low-brow game of chicken between two personalities, it was one of basic chance.

In a way, this last statement is simply framing. Hallway discussions, last-minute calculations, and games of chicken include the same chance that decided those events in 1962. However, rather than recognizing the role that chance plays in even our most dire situations, we grasp for someone to mold those events into the familiar landscape of strategy. The more dire the consequences, the more we poke and prod in our efforts to form a jumble of words and actions into a recognizable shape. Our pundits have been all too happy to fill this order. What’s more, they’ve found a seemingly universal totem through which they can distill their lessons: chess.

A cursory Twitter search yielded instances of the commentariat using chess to describe: Barack Obama, Mitt Romney, James Clapper, Joe Biden, Bernie Sanders, Hillary Clinton, and failed “Meats” student Rick Perry, whose mere existence on the same dimensional plane as a chessboard is surprising, to say nothing of his alleged use of one. And that’s just US leaders. Stretching further back, one stumbles upon deliberative games between Truman and Stalin, Bismarck and Pope Pius IX, and Napoleon and Cornwallis, to name only a few.

However, nowhere does the skeleton threaten to break through the hastily applied skin more than when the actions and words of President Trump have been molded by pundits in an effort to stay ahead of shifting goalposts and explain away counterproductive actions. In doing so, supporters, anti-anti-Trumpers, and the “let’s hear the other side”-rs have contorted themselves into positions that would make the director of The Exorcist blush. As the consequences become more dire, they manage to shout, “Well, perhaps he isn’t playing chess, but surely he’s still two moves ahead of Kim Jong-un,” while their necks jerk at gruesome right angles.

It’s not unnatural that we’ve grasped for strategy where none is to be found, particularly when “fire and fury” is what’s being offered by our leaders, something recognized by Conrad in Gambling and War. Still, he asks us to look at world leaders not through a wholly strategic lens, but through one including chance. Even in ideal circumstances, an actor on the global stage will have a distribution of probable outcomes of what might occur given his or her actions. Instead of “anticipating the moves of one’s adversaries, developing countermeasures, and implementing carefully prepared strategies,” like what’s found in the game of chess and shaped to fit the handshake of Trump or the trolling of Putin’s foreign ministry, the decisions surrounding war come down to recognizing the cards held, considering the hand of one’s opponent, determining the likelihood of victory, and deciding how much one is willing to lose over the course of the game. Otherwise, we’re all pigeons.


One enters Conrad’s game room and looks around. The center table lacks the merry-go-round of roulette, the quilt of craps, or the half huddle like blackjack. Instead, it’s the simple, oblong shape of a poker table. Two men sit on either end with cards in hand, each watching the other. The one on the left wears an orange tint with a sheer curtain of hair that wafts over his forehead. The other is a pudgy young man in a high-collar suit. His hair is shaved closely on the sides and rises to a sort of ploof upon his head. He keeps a pair of glasses in his hand should the need for intellectualism arise.

In Conrad’s model, this first stage of the game revolves around a few components. One is the fact that each player only knows what’s in their hand and later what’s on the table. This imperfect information is the source of deceit they’ll use, but also the very reason they both keep playing. After all, if you knew your opponent’s cards ahead of time, one of you would never enter a losing game. There’s a third person at the table, too, different from the two men. They might be an older, formally dressed man or women wearing a uniform. Every time you try looking straight at them, they seem to disappear into the background. In this silent dealer lies the dual core of gambling as a model for world events: probability and strategy. Players are bound to the table. They might ultimately be responsible for their actions, but they’ll never be the source of a winning hand. Ultimately, that honor goes to the dealer.

So the game advances. In the first round of betting, the players only have their two cards. It’s here where they have a single shot to push off the course of war before it begins. Perhaps they signal their credibility in a show of force or a deployment of troops to a border. Maybe they try to divert their opponent’s attention, knowing they have a lesser hand but hoping that opponent will decide to force conflict elsewhere, at another time. No matter the specific cards, it’s here where each player is most optimistic. Otherwise, they never would’ve entered the game and bet the blind. As it is with war. Each believes the terrible cost to be worth the outcome. In all instances, one will be wrong.

Once a player joins the game with the blind, the only thing to do is play. Each of Conrad’s gamblers have a few important tools at their disposal: bluffing, a measure of credibility, and a store of resolve. It is in the first where actors with lesser capabilities can match a superior player by appearing larger or more resolute. The second allows for their actions to have weight — the costly bet in the middle of a hand that signals to the other it might not be a bluff. It’s built up or worn down over the course of multiple bets. Both randomness in a player’s actions as well as reliability factor into this equation. Finally, resolve. The metric that even the most skilled player has only a slight glimpse of. It’s the private line of credit, or the watchful spouse, of their opponent. In the case of the world stage, the leader’s people. It determines how they play over the course of the match as well as when they’ll leave the table for good, or for now.

Conrad’s model is disappointing. When an outcome is ascribed to chance, as it often does in the course of millions of decisions that are made in a complex endeavor like war, it frustrates us. We want, we need, to understand. When we hear someone saying, “Why didn’t we go to war with the Soviet Union during those days in 1962? Well, the chance was there; it just so happens we didn’t,” it shakes our belief in leaders and replaces their power, or at least a portion of it, with a cold and abstract statistical measure: x > 73 percent, y ≈ 52, (z, 21).

But that doesn’t mean it’s not a useful, or indeed the correct, manner of engaging with the actions of leaders. With this in mind, we begin paying attention to the players at table. The brash, ocher man and his younger opponent with the equally funny coif. We look at their shifting stacks of chips, the beads of sweat on their foreheads, the intense concentration on their cards, as if willing the suit of their queen to shift from clubs to spades. We stare at the older man’s scotch-taped tie and try to pick out if he’s the bull in the china shop that scares off the storekeeper, only to change into a thief once he’s gone. Or perhaps he’s the type to slip in unnoticed in order to take measure of his opponent before the other knows anything about him. Each time we think we’re on the edge of understanding, he throws our impression out the door.

While the model of poker includes both strategy and probability, that does not mean that an individual needs to make use of both. There’s always a gambler in the casino who’s just there to play the odds, grab a few drinks, and, if he’s lucky, manage to stay in the black the rest of the night. It’s here, in this wing of the casino, where we find our president.

President Trump’s actions are driven by a number of motivations: a desire for positive coverage, the abstract, ephemeral notion of ratings, and a need to be personally well liked (if not professionally), among others. He is not, however, driven by a strategy, or perhaps even a coherent worldview. Despite the contortions of his followers, there is little evidence the president’s shifts stem from anything more than personal whims and vanity. In fact, if anything, the president seems disinterested in developing such a strategy, particularly in matters of foreign policy where he prefers to delegate responsibilities outside of pageantry to “his generals.” However, this doesn’t mean that the world ceases to size him up. The gambler still plays the game against opponents, even if he doesn’t pay attention to anything outside of his hand.

What then to make of this lack of strategy, particularly when the stakes are so high? Or, more acutely, is no strategy sometimes better than a bad one? I went back and forth on this idea. I think it’s important that government officials and citizens recognize that uncertainty plays a more profound role in shaping world events than the rare chess master and doing away with the complicating factor of strategy, if only for a moment, helps distill this lesson. We also know better than believing poorly developed strategies have a zero bound, particularly if they’re coupled with interventionist tendencies.

As it relates to Conrad’s model, an element stands out when trying to wrap one’s mind around this lack of strategy: the concept of credibility. This constantly shifting notion exists before the game even begins and gradually rises or falls with each action of an individual. It plays an important role both when making honest statements or attempting to deceive. And it’s here where we start to reach the core of the problem with having no strategy. To the Trump administration, words, even actions, have little meaning.

With each word uttered or action taken (or not), the pit of credibility grows more insurmountable. At times, the Trump administration has even trumpeted this idea, though admittedly using different words. “Why should we telegraph where, when, or how we’re going to act,” they seem to ask. If this sense of surprise was accompanied by their positive claims being followed to a T, there still might be hope. Instead, the form of specific actions, or whether any action will take place at all, is unknown until it happens. Other times, it simply disappears into the ether. Some opponents may try to keep the public’s attention on this fact for a day or week, but it’s almost always in vain. There’s always another crisis to occupy one’s attention.

But now, again, we’ve started walking toward that roof’s edge. I could continue discussing credibility, the United States’s place on the world stage, and what it would take to replace it, but in these circumstances, it matters little. All rest a few paces back with a leader cognizant and attentive of such things. Instead, in the meantime, we wait and remember that the world turns on both strategy and chance. A vacuum exists where the former should be. In this environment — closer to interventionism than not, a jumble of words and actions defining world events, and a host of unpalatable leadership traits existing in Washington, DC, all the parts of Conrad’s equation, save chance, are washed away. Should this frighten us? Absolutely. Even if an ace high is sometimes all it takes to win a hand.


Adin Dobkin is a writer based in Washington, DC.

LARB Contributor

Adin Dobkin is a writer and journalist. His work has been featured in The Atlantic, Foreign Policy, and elsewhere. He currently lives in Washington, DC.


LARB Staff Recommendations

Did you know LARB is a reader-supported nonprofit?

LARB publishes daily without a paywall as part of our mission to make rigorous, incisive, and engaging writing on every aspect of literature, culture, and the arts freely accessible to the public. Please consider supporting our work and helping to keep LARB free.