All the Ways Ukraine Can Win (or Lose)


Many people agree that America’s decline began with reality TV. Ever since The Bachelor and The Jersey Shore hit, Americans have pretty much withdrawn from community events so that they can watch bimbos argue over whether it is okay to bang on the first date or if it is okay to take the smush room for two straight Saturdays.

It got so bad that we even elected a reality TV star president in Donald Trump.

But our national fixation on unscripted TV hit a whole new level of depravity this past week due to the fact that millions of us are now hooked on Twitter videos of 25 year old Ukrainian soldiers and 21 year old Russian soldiers attempting to kill each other in a war. It is 100% cringe. Honestly, I feel like The Squid Game is on live TV. We are devouring this war like it’s March Madness, but with guns.

The saddest part? The best reality TV shows always have a winner. And that means a loser too.

So as we get used to the notion that a serious war is happening in Europe, it’s time to ask the question of — how will it end? Who will Vlad Putin give the final rose to?

Our friends over at Polymarket recently posted a prediction line on this subject. It’s fascinating and also tricky.


This question is even more interesting from a bettors’ standpoint, because the war in Ukraine can go in a lot of directions and on a few different timetables.


First, let’s summarize the way that Zelenskyy can be desposed:

SURRENDER. Right now everyone in the Fake News Media (FNM) is cheering hard for Ukraine and applauding the fact that untrained civilians are arming themselves to fight. However, this bugle blowing is morally gross. Vlad Putin is 100% going to use these civilian militias as a reason to target everyone outdoors in a puffy jacket for artillery bombardment.

The point is that everyone is acting very brave right now, but sh*t is about to get genuinely awful. And as more and more of today’s “heroes” become tomorrow’s dead, there’s a reasonable chance that Zelenskyy will surrender.

Why let so many die if there is no hope of victory?

CAPTURE. Zelenskyy is making a bigger deal about staying in Kyiv than LeBron made about leaving Cleveland. This comes with the massive drawback that the Russians can encircle the city and eventually capture him. This is a virtual certainty if he stays in the capital much longer.

Let’s be real about it, the Ukrainian army 100% does NOT have the horses to break a siege unless they can con Joe Biden into lending them a carrier battle group for a few days.

DEATH. Russia has tons of cruise missiles, airplanes, and artillery pieces with very shady morals guiding them. Zelenksyy would not be the first Ukrainian head-of-state that Russians have attempted to assassinate. Also, as said above, expect to see saturation bombing of Ukrainian cities, including whatever place Zelenskyy takes his afternoon tea.

But the perils above also understate the number of outs Zelenskyy and his government have.

First, wars take a while.

The fastest conquests in the modern era are measured in weeks, not days. It took George W Bush about 1 month to make the Iraqi army into his personal prison b*tch detachment in 2003. It took Hitler about 6 weeks to conquer France. Both of these were absolute debacles for the defense, which isn’t what we’re seeing in Ukraine.

The only conquests that moved faster were ones where the defenders realized that they had a lower chance of victory than Zac Effron does of winning an Oscar, like Czechhoslovakia in 1968 and Kuwait in 1990.

So a surrender around the April 22 resolution date would give Putin a little extra time compared to the fall of Baghdad and Paris. In a way, that makes sense because the only things Russia does better than the USA is hockey, alcoholism, and cyber crime.

Second, the defense tends to win as long as they just don’t quit fighting.

Afghans and Vietcong did not beat imperial powers because of their superior technology and prowess. They beat them because they were willing to fight indefinitely and stomach brutal losses until their occupiers lost interest.

In the context of this bet, Ukrainian forces continuing to resist through April is not hard to imagine.

Third, Zelenskyy and his government could always flee Kyiv.

If there is one thing I know about war’s losers, it is that they tend to be sore losers. For example, Charles de Gaulle fled France after it fell in 1940, and just because he had a radio, a funny hat, and a posh apartment in London, people believed him whenever he said that he spoke for his nation’s legitimate government.

In 1949, after Mao took over China and made it more communist than San Francisco, Chiang Kai-shek’s government dee-deed to Taiwan. The UN continued to recognize his regime as the legitimate China until 1971.

This plan is an option for Zelenskyy. And should he evacuate to a safe location outside of Kiev, while Putin installs a pro-Russian anti-christ pope leader in his old throne, it sets-up a rules conflict on Polymarket. As written, the resolution source could be the UN or Ukrainian government websites — and those could be written by very different authorities.

So, the endgame is…

It doesn’t look like Putin can achieve a bankable strategic victory in Ukraine, at least as long as the locals hate him so much that they’ll drop their barista smocks and pick-up Kalashnikovs, but there’s no way that Ukrainian forces can hold Russia off indefinitely. All credible sources have said that Putin is about to turn it up to 11 on them, and that’s bad news for a Ukrainian military that can barely handle the Russian advance at its current easy listening volume.

Will the Russians win the battle? Absolutely.

Will they win the war? Maybe in the short term, but that’s it.

Can Zelenskyy last another 6 weeks? That’s a question of odds. I like them under 49c.

For those of us watching reality from our couches, this war is a geopolitical elimination challenge. Will Ukraine survive and receive tribal immunity from NATO, or will Putin snuff out its torch with cruel inhumanity?

Stay turned, my friends, for the answer.


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