How Long Can Ukraine Hold Out?
After being hung out to dry by NATO and America, Ukraine’s brave defenders are giving Putin’s forces a solid kick in the teeth.
NOTE: Originally published on Medium 2/28/2022.
The women and men of Ukraine’s fighting forces have proven Ukraine is a free country — more of one than America, to be honest.
So Slava Ukraini! Heroiam slava! Слава Україні! Героям слава!
Trouble is, as much as I dearly wish for Ukraine to win, Kyiv is still badly outmatched in this fight. A partition of the country between free and occupied zones appears likely if ceasefire talks fail, as I’m afraid they will.
EDIT 12/22/22 — Ukraine is more than holding on, it’s winning. The first defensive line more than held, and the counterattack this summer was fierce. However, the question of the future remains, because support for Ukraine become shakier by the day.

Putin is in dangerous waters now. His own rhetoric about “denazification” has trapped him.
But the bear is mighty powerful. And Russia’s forces have been holding back much of their firepower. Once that changes… more heroes will be born.
Would that they did not need to be.
Even heroic resistance gets ground down over time. We’ve only witnessed the first wave of this invasion, and when the Russian second echelon strikes with full force, things are gonna get even bloodier.
Ukraine’s basic military problem remains: outnumbered and outgunned, over time the weight of Russian firepower will take an awful toll.
Ukrainian forces desperately need an influx of high-tech modern supporting equipment, particularly air defenses and combat aircraft. Otherwise, once Russian forces adapt to the level of resistance they are facing — and clearly did not expect to — Ukraine will be ground down in the most brutal way.
The initial days of the conflict have been a surprise for many observers because of how inept the Russian attack appears to have been.
Most, including myself, anticipated a more limited, focused attack on the east for the exact reason Russian forces have failed to seize Kyiv already, despite that craven political hack Joe Biden insisting for weeks the city would fall in 1–2 days, all but telling Putin to go ahead and take it.
Modern warfare is a difficult business. Pundits love to shout “blitzkrieg!” whenever tanks get used and repeat tired old myths about combat drawn from World War 2 movies.
Real war is about organization above all else. Germany crushed France and Britain in 1940 mostly because radios were in almost every German vehicle. They could talk and coordinate better than their opponents, allowing them to move faster than predicted and so surprise their targets.
Putin’s forces were not organized properly for the kind of combat Ukraine’s tough defense has forced them into. Based on years of Russia-watching and studying the social dynamics powering conflict it seems clear that Putin either acted on bad intelligence or let his own propaganda cloud his judgment.
It appears the initial invading forces were told they would meet little opposition — this would be a simple march to Kyiv to topple a government its people wouldn’t fight for.
A number of Russians allegedly captured have indicated they had no idea they were invading Ukraine. While this could be just what they’re told to say and without independent verification we have to assume that most of what Kyiv says is propaganda, even if well meaning, Russia’s opening attacks were oddly weak given the stakes.
Russia could have launched an absolutely overwhelming missile assault on day one designed to shatter Ukraine from top to bottom. 2000 missiles, not 200. Instead, Russia’s opening salvos were clearly designed to try and cut Ukraine’s military leadership off from the bulk of its forces but not shatter the country or the entire Ukrainian military.
Putin appears to have bet that Ukraine would collapse just like Afghanistan did. After all, Joe Biden spent months insisting Kabul wouldn’t fall to the Taliban then it went down in a matter of days. If Putin truly believes Zelensky is an American puppet, Afghanistan proved to the world there was a decent he might simply flee the country to save his life.
Heh, about that :)
Just like when America invaded Iraq in 2003 — the model Putin appears to have used as part of his “see, I’m as tough as the Americans” message — the invaders wanted an intact country to rule through a puppet.
But this bet has turned out to be incredibly bad, especially given that Putin had a much better path to divide his opponents and slowly strangle Zelensky’s government. Putin could have continued to exploit divisions in NATO over how far to support Ukraine, instead he’s managed to convince Germany to rearm.
When Germany decides the time has come to start boosting military spending and the rest of Europe cheers, you know the world has changed.
The danger of a country being run by a powerful leader is that humans tend to tell powerful people what they want to hear. This easily leads to a groupthink feedback loop where obvious truths wind up ignored.
Classic case that isn’t Iraq in 2003: the failed Bay of Pigs invasion Kennedy launched to overthrow Castro in Cuba 60 years ago.
Putin could have simply miscalculated — no one is infallible. Even the clever ones are prone overstep when they scent weakness.
But equally likely is that he and his clique came to believe in a mythical version of reality driven by Biden’s abandonment of Afghanistan and a desire to prove Russia can do regime change better than America.
Almost a week into this war, calculations are now shifting. The not even veiled threat of going nuclear if NATO intervenes is a sign Putin is scrambling to adapt.
He knows this is now set to be a long, difficult war. Even if Kyiv falls and Ukraine pulls back to defend its western half, it’s not gonna end.
An animal with no avenue of retreat is the most dangerous kind. And Putin can’t go back now — barring a miraculous ceasefire both sides observe, so he is likely to intensify every aspect of the attack.
Russia had always assembled too few troops to occupy Ukraine outright. The plan was clearly a swift regime change operation that would give Ukraine’s army a new political leader who would use it to tamp down resistance on Putin’s behalf.
Evidence of this can be seen in the way Putin’s attack first focused on major urban centers like Kharkiv and Kyiv instead of bypassing them and laying a siege until their mayors were forced to negotiate a surrender. That had to be an attempt to simply seize power while Ukraine’s government was cut off and reeling from the first wave of attacks.
Russia thought paralyzing Ukraine’s government and negating much of its air force and major air defenses would leave ground units isolated and willing to surrender. That was wrong — but Russian forces still badly outnumber Ukraine’s.
This explains why Russian forces near Donbas have not pushed forward as expected. A major chunk of Ukraine’s army remains entrenched in the east, pinned in place by the threat of attack, a move intended to make it easier to get to Kyiv without wiping out forces Putin hoped might follow his orders.
Clever — but too clever by half. The shock of coming under widespread attack stoked Ukraine’s sense of identity, and so Ukraine has fought back. The anger is so high now that Putin faces a blood-drenched insurgency if he tries to hold too many major cities.
Putin’s ambitious plan to seize Ukraine at a stroke has failed. Even if Kyiv falls and Zelensky is killed or imprisoned, a Ukrainian identity has been born as a consequence of this war that will not be extinguished.
Someone, perhaps a general, will rise to succeed him. Ukraine will almost certainly fight on unless Russian demands are limited to Donbas and Putin gives up the dream of regime change.
Putin has likely recalculated. He’s shaking his nuclear spear to remind NATO to keep out. Now he’s likely to move to split Ukraine apart, surrounding cities and cutting them off, encircling Ukraine’s main fighting forces.
This is where Russia’s immense reserves of combat power relative to Ukraine’s come into play. As bold as Ukraine’s defenders have been, Russia has still only moved something like half to two thirds of its forces into Ukraine. Up to half of Russia’s attacking forces have not yet engaged in direct combat, and right now they’re pushing through areas Ukraine doesn’t have the forces to defend.
And though Ukraine’s government and those who hope to see it survive aren’t admitting it openly, it is likely that Ukraine is suffering proportionally as many casualties as it inflicts. Both sides are likely losing 1%-2% of their combat forces every day they fight. Over time Russia will take more casualties — but it has more blood to shed.
A good rule of thumb is to take whatever kill claims one side asserts and divide by three. Figuring out exactly what happened in a given incident is nearly impossible without a full investigation, as when a jet gets shot down or tank gets blown up multiple people see and report it.
American media reports are also heavily biased in favor of Ukraine right now, while Russia keeps mum about most of its losses. But the simple fact that Ukraine has held off heavy Russian attacks in the northeast while Russian forces are swiftly advancing in the south implies Russia is slowly finding gaps to exploit, as their doctrine generally suggests.
Over time this is going to start getting more and more lopsided. Ukraine’s best forces are in the east, fighting hard for Kharkiv but facing flanking attacks as Russian second echelon forces find holes along the edge of their positions. In the north, Ukrainian forces have held ground near Chernihiv and Sumy, but breakthroughs near Konotop mean they are in danger of being cut off from Kyiv in a couple days.
And the southern front has more or less collapsed. The push from Crimea got across the Dnieper, and a portion of the forces coming from there are rushing up the Dnieper to get behind Donbas at the same time another thrust bypassed Kharkiv and also outflanks Ukrainian forces in the east.
Although Russian air superiority remains challenged, for all intents and purposes it exists over the western half the country. The rumored “Ghost of Kyiv” is likely not just one pilot (though it is possible) but a composite of a number of Ukrainian pilots who have managed to disperse their aircraft to avoid attack and launch sorties as they can to harass Russian forces.
Russian aircraft like the venerable MiG-29 can operate from highways and rough air strips, a major advantage over American designs only matched by Swedish aircraft like the Gripen. And Su-27 fighters have incredibly long range, meaning airfields near the Polish border are probably generating sorties. And some drones are having successes — just, Ukraine needs a whole lot more.
But over the battlefield Russia clearly has the advantage in the air. Ukraine’s mid-ranged air defenses have survived in some numbers, but they will keep coming under attack and once gone they’re not getting replaced. Every time a surface to air missile system turns on its targeting radar it exposes itself to a counter-strike. [Note 1/23/23 - fortunately, pop-up attacks, a form of guerilla SAM warfare, helped even the odds and inflict too many casualties on Russian pilots to sustain operations over the entire country]
Ukraine’s forces so far have been brilliant at taking advantage of what texture exists on these flat battlefields by pulling Russian forces into towns then counterattacking. But notably Russia’s powerful rocket artillery is not, by and large, flattening whole towns and neighborhoods as it could — at least not yet.
The trouble is that the longer this fight goes on the more brutal it will get. Putin will realize a full conquest of Ukraine is not possible, given that he’d need Ukraine’s own forces and a compliant puppet government to maintain control of a California-sized country in the face of even a mild insurgency.
So now Putin has a strong incentive not to take over, but simply destroy large parts of Ukraine. If the country cannot be held, now that Ukraine really is a battleground with NATO he has no reason to let Ukraine survive as an intact country.
From the evidence I’ve seen Russian forces have on the whole been behaving with remarkable restraint towards Ukrainian civilians. Yes, hundreds have died and many more will yet, but these don’t appear intentional — in a congested environment, rockets and missiles sometimes hit apartment buildings trying to blow up something else. [Edit 1/23/23 - at first it might have been accidental, but Russia’s behavior after the opening days, along with the atrocities revealed in places Ukraine later liberates, indicate it hasn’t always been. Russia’s open brutality was one of the real surprises of this fight, as Russia wasn’t expected to “Slavic brothers” like it does Syrians.]
Once cities are cut off from the surrounding countryside, starvation in the trapped population becomes a real concern. Putin himself lost a brother in the vicious siege of then-Leningrad during the Second World War, a nightmare that forced locals to mix in dirt with the tiny rations of flour they could obtain to stave off hunger pangs.
He knows how horrible this kind of warfare is. He might now count on it to break Ukraine’s will to resist. Propaganda aside, the longer people are exposed to violence the more they will do anything to make it stop.
This is not to minimize the brutality of this war or Russia’s responsibility for launching it — even if Biden’s bungling of the diplomatic side is something he should have hung around his neck for all time, and probably will, Putin chose this war.
Whether he got bad intelligence, miscalculated, is just this monstrous, really is insane, or some combination of the above, Putin is trying to kill Ukraine. He always has been — he just chose a more violent route to achieve his objective than I anticipated.
The real question now is what the rest of the world is willing to do to stop him.
A key lesson of history is this: once guys like Putin start, they aren’t stopped until someone forces them to. For the foreseeable future Russia will be a pariah state that we have to assume is willing to fight a world war to control Ukraine.
This means that it doesn’t matter what nuclear threats Putin makes, how much sanctions eventually cripple Russia’s economy.
What matters is whether enough combat force is available to stop whatever move he makes.
Ukraine cannot be allowed to fall. I think Europe realizes this — after all, Germany is rearming. NATO is obsolete, as I argued last year, and the proof is the fact it failed to do its one job, the reason it was founded in the first place: deter Moscow from war.
The European Union has to take the lead. Its member nations must do all they can to make sure Ukraine doesn’t fall.

Ukraine is actively calling people with military experience to join its defense. International battalions need to be established in the west of the country as soon as possible and equipped with whatever gear they can be trained to use over the course of 4–6 weeks.
This must include air power — there are plenty of former military pilots out there who could be given donated F-16s and begin working to control the airspace of western Ukraine. And every nation willing to send air defense systems should, with NATO deploying Patriot and THAAD systems right up to the Poland-Ukraine border to create a protected bubble Russia can’t easily hit.
Drones are cheap, relatively easy to operate, and deadly — these should be sent and production centers to make more as well. And countries like America and Germany with the funds should begin buying former Soviet and Russian military gear from the many countries around the world who have bought it in the past. This needs to be shipped directly to Ukraine to equip new fighting formations over the coming weeks and months.
Further, air bridges to allow humanitarian aid to cities under siege need to be organized — even at the risk of interception by Russian aircraft. A Berlin Airlift for the 21st century, directly protected by European air power.
You can’t fight a war on your opponent’s terms. Nuclear threats must be disregarded, because once you give into them once that card will be played again. European countries should also begin the process of formally integrating Ukraine into the European Union, perhaps giving it special status, and consider defensive air patrols that do not engage Russian forces directly, but make it difficult for them to operate.
The war in Ukraine now goes one of three ways, and the fate of Europe hinges on the outcome.
Option 1 is a cease fire that probably gives Russia Donbas and the Azov coast but preserves most of Ukraine’s independence. Option 2 is a total Russian victory after an all-out assault, followed by years of repression of the population. Option 3 is a long, painful war that continues until Ukraine is liberated in future years or Russia pulls back — or collapses. [Note 1/23/23 - we got option 3.[
Years down the road, this moment will probably mark the point of no return for Russia. Once the fight to succeed Putin inevitably begins, the country is likely to fragment into nuclear-armed city-state mini-empires.
This hard future probably cannot be avoided any more than America’s own collapse and division. The world has entered a new age — the assumptions of the Cold War and the global liberal order were always false.
And so long as the powerful remain so, international wars never truly end.