Lieutenant, you are looking at the only Starfleet cadet who ever beat the no-win scenario.” – Dr. Leonard McCoy, Star Trek II: The Wrath of Khan

Nested deep within the Star Trek canon is the Kobayashi Maru, the training simulation all Starfleet Academy cadets must encounter prior to joining the fleet. The scenario is designed to push future officers to the edge of their limits, testing leadership ability under duress, ethical decision-making, resilience, and, inevitably, humility. From the small screen to the big screen, from scores of novels to decades of comics, the Kobayashi Maru conveys a singular concept: that at some point in our lives, we must contend with the “no-win scenario.”

Unless you’re James T. Kirk, who – while seemingly marooned within the bowels of the Regula planetoid in the 1982 film, Star Trek II: The Wrath of Khan – reminded us, “I’ve never believed in the no-win scenario.” Rather than face certain defeat and humiliation in the Kobayashi Maru scenario, he reprogrammed the simulation. “I changed the conditions of the test… I don’t like to lose.”

Where is all of this leading? Ukraine is Putin’s Kobayashi Maru.

Putin’s No-Win Scenario

Russia’s 2022 invasion was supposed to be a quick operation to capture Kyiv, topple the central government of Ukraine, and install a puppet regime friendly to Moscow. According to a March 2022 report from the Institute for the Study of War, Russia’s main effort was intended to envelop Kyiv from the west while supporting efforts would close the encirclement from the northeast and the east. On paper, it was a brilliant plan.

From the outset, Putin’s gambit badly underestimated Ukraine while at the same time overestimating his own military’s capabilities.

Within a month of invading, Russia was forced to concede the Battle of Kyiv, withdrawing the scattered remnants of its forces and refocusing on completing the occupation of the Donbas region. Russian formations, seemingly incapable of conducting combined arms maneuver, were decimated by outmanned, outgunned, and outnumbered Ukrainian forces.

The losses mounted for Putin’s forces. By the close of 2023, intelligence reports suggest that the invasion has cost Russia 315,000 dead and wounded, roughly 87% of the total with which they began the war. Among those losses were at least 16 Russian generals and one admiral, and the resulting impact on leadership cascaded across the entire force. Equipment losses have been equally staggering, with Moscow losing a reported 6,257 tanks, 9,067 artillery systems, 11,621 armored combat vehicles, and 331 military aircraft. While Ukrainian losses have also been staggering, Russia has not been able to overcome its own ineptitude on the battlefield to translate those losses into an advantage.

reprogramming the sim

After eight months of early brutal losses, Putin recognized the situation for what it was and committed to a punitive expedition, putting civilian infrastructure in his reticle. If he couldn’t break the will of the military, he’d break the will of the people. His forces targeted schools, hospitals, markets, and residential areas. They have routinely staged attacks on power plants and utilities; in one day alone, they launched 43 cruise missiles – 36 of which were shot down by Ukrainian air defenses – against energy infrastructure.

The humanitarian toll has been brutal. At least 10,000 civilian – and more than 560 children – have been killed and another 18,500 injured. An October report prepared by the Congressional Research Service exposed the systematic moral assault on the people of Ukraine by Russian forces, detailing alleged war crimes ranging from sexual violence and widespread abduction (and relocation) of children to abuse of prisoners of war and intentional attacks on the civilian population. No fewer than five mass grave sites have been subsequently discovered in areas previously held by Russian forces.

When that didn’t break the will of the country, he resorted to mercenaries and even violent criminals who exchanged their freedom for almost certain death in a futile war (and those who managed to survive continued where they left off before being sent to prison). These decisions didn’t improve the situation at the front and Moscow continued to bleed forces, losing an average of nearly 500 men per day in a war that was supposed to last three days.

What will Putin do next?

As Ukraine approaches the anniversary of Russia’s invasion, one question persists: What will Putin do next?

To answer that question, you have to understand Putin. First, he doesn’t like to lose. And his grip on power—as strong as it may seem to us—depends on him not losing. He’s tried to “change the conditions of the test,” but nothing has worked. His vaunted military reforms of the past decade have ultimately made his army weaker rather than more formidable. Second, he’s not hamstrung by a sense of morality. He’s not afraid of the United Nations or the International Criminal Court; he knows no one outside his own borders will ever hold him accountable. That makes him an especially dangerous opponent, someone who will go to any lengths possible short of nuclear war—we hope—to achieve his goals.

There are indications that Putin plans to see his invasion through, fighting on for at least five full years. If his sights are limited to Ukraine—something that remains a matter of some debate—then he will likely attempt to disrupt NATO’s ability to provide uninterrupted support to Kyiv, using a focused influence campaign to sow political discord and chaos. He’s already seen firsthand how susceptible the West is to such efforts, and experience with election interference in the United States during the 2000 presidential race provides a ready template for the future.

That influence campaign may already be ongoing. According to Kremlin documents, Russia is already actively working to subvert French support for Ukraine, “promoting political discord in France through social media and French political figures, opinion leaders, and activists.” In the United States, “Russian interference in the 2022 mid-term elections has had serious consequences for Ukraine.” And Russian disinformation has become a focal point for NATO, as the treaty organization has made a concerted effort to debunk the false narrative intended to create instability and opposition for their support of Ukraine.

One thing is certain: with another U.S. presidential election looming, the Olympics on the horizon, and the sovereignty of Ukraine hanging in the balance, 2024 is going to be a wild ride.


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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a co-founder and emeritus board member of the Military Writers Guild; the co-founder of the national security blog, Divergent Options; a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal; a member of the editorial advisory panel of Military Strategy Magazine; and an emeritus senior fellow at the Modern War Institute at West Point. He is the author, co-author, or editor of several books and is a prolific military cartoonist.