One way to answer the question in the headline is “It already has.” Even to a rank amateur like me, it was clear by *day three* that Putin was facing a strategic debacle. He misjudged Ukraine’s desire and ability to resist, he misjudged the strength of his military, and he misjudged the west’s willingness to paralyze Russia’s economy with sanctions. “No Russian leader since Tsar Nicholas II has done his country so much harm, so fast, as Vladimir Putin,” David Frum tweeted a few days ago, marveling at how diminished Russian power has been by Putin’s folly in the span of a few weeks.

Nothing that happens in Ukraine from this point will undo that. It’s a fiasco.

But a strategic defeat is distinct from defeat on the battlefield. Even optimists have assumed that Russia would eventually brute-force its way to controlling Kiev and other major Ukrainian cities. The “real” fight for Ukraine would come after that when Russia’s occupying forces and Ukraine’s insurgency would wage a war of attrition. Eventually Moscow would run out of patience and withdraw, but “eventually” could take months. Years. Decades, conceivably.

But what if the optimists were too pessimistic? What if Russia is facing near-term defeat on the battlefield as well?

Realistically, there are three ways in which the Russian army might lose:

1. Putin is toppled in a palace coup and his successor withdraws from Ukraine. That’s unlikely, but stay tuned.

2. Putin himself withdraws voluntarily, seeing no prospect for victory. Normally that would be unimaginable, as he’s staked his legacy on conquering Ukraine and would surely fight to the last Russian to save face if able to. But the massive economic damage done by western sanctions is a black-swan event. Could we reach a point in the near term in which the Kremlin simply can’t pay the bills to keep its army going?

I assume Putin would prioritize military spending above all other domestic concerns as the money runs out, so desperate is he to salvage some prestige in Ukraine. He’ll let the lights go out in Russian cities rather than pull the plug on his glorious adventure. So, no, this probably isn’t how the war ends either.

3. Underequipped, taking heavy losses, and plagued by low morale, the Russian military just sort of … quits. Francis Fukuyama dares today to think the unthinkable, predicting a battlefield rout of the Russian bear:

Russia is heading for an outright defeat in Ukraine. Russian planning was incompetent, based on a flawed assumption that Ukrainians were favorable to Russia and that their military would collapse immediately following an invasion. Russian soldiers were evidently carrying dress uniforms for their victory parade in Kyiv rather than extra ammo and rations. Putin at this point has committed the bulk of his entire military to this operation—there are no vast reserves of forces he can call up to add to the battle. Russian troops are stuck outside various Ukrainian cities where they face huge supply problems and constant Ukrainian attacks.

The collapse of their position could be sudden and catastrophic, rather than happening slowly through a war of attrition. The army in the field will reach a point where it can neither be supplied nor withdrawn, and morale will vaporize. This is at least true in the north; the Russians are doing better in the south, but those positions would be hard to maintain if the north collapses.

Putin will be ousted in the aftermath of his failure, Fukuyama further speculates, and China will rethink its designs on Taiwan having seen what sort of trouble an invader can run into when its air force isn’t prepared for complex operations.

Is that too good to be true? Probably. But other knowledgeable observers are also beginning to whisper about the prospects of a Russian battlefield defeat:

On Feb. 28, Mikk Marran, the head of Välisluureamet, Estonia’s foreign intelligence service, told New Lines that he didn’t believe Putin could “keep up an intensive war for more than two months” and that ultimately “Russia will not win this war.”

A senior Estonian analyst with years of experience tracking Russia’s military affairs concurs with that assessment but doesn’t even think it’ll take another two months to bear fruit — it already is doing so…

“If Russia does not achieve a remarkable advance by the end of this week, it is difficult to see how [the advance] should come at all,” Karl said late this week…

If Russia doesn’t achieve remarkable success in the next few days, it would leave the door open for Ukrainian troops to start large-scale counteroffensives. The first aim would be to drive Russia out of the country in the north around Kyiv and Kharkiv.

There are no skilled reinforcements waiting back in Russia to relieve the front-line troops, which is why Putin has gone sniffing around for help from Syria and Belarus. And the sheer amount of men and equipment lost already to Ukrainian attacks means that Russian units left in the field aren’t functioning at optimal levels. At some point, as losses mount and resupply grows even more difficult, the military will become ineffective. And that point may not be long in coming.

You can see, then, why Zelensky is reluctant to make any deals with Russia despite the terrible suffering in cities like Mariupol and the pressure being put on him by allies. It’s an open question whether Russia can sustain this offensive for much longer, which means time is on Ukraine’s side and he knows it. Conversely, you can understand why Russia is resorting to terror tactics like kidnappings and attacks on hospitals and mosques. The clock is ticking on them; their best chance at an “honorable” outcome is to try to frighten the Ukrainians into suing for peace before Russia’s war machine breaks down.

It’s no coincidence that the chatter about a possible chemical weapons attack also picked up this week, I’m sure.

Another clue to Russia’s desperation was the threat their deputy foreign minister made to NATO this morning:

Russian Deputy Foreign Minister Sergei Ryabkov speaking on Russian state TV: "We have warned the US that pumping weapons [into Ukraine], which they have orchestrated, from a number of countries is not just a dangerous move, it also turns these convoys into legitimate targets." pic.twitter.com/3NM3Xl7SLr

— Will Vernon (@BBCWillVernon) March 12, 2022

If Russia can cut the supply of western weapons to Ukraine, that would increase the pressure on Zelensky to cry uncle before Russia does. But why should we believe at this point that the Russian air force could target those convoys even if it wanted to?

I have yet to see any evidence of Russia having the capacity to strike Ukrainian military convoys that are moving in broad daylight on main roads within Ukraine, apart from immediate frontline areas. All the strikes outside tactical combat areas were on static targets so far.

— Yaroslav Trofimov (@yarotrof) March 12, 2022

My guess is that the Russian infantry massing around Kiev isn’t even going to enter the city. They know what sort of losses they’d take in urban combat; there’s no reason to think they could outfight the Ukrainians on their own streets. More likely is that they’re going to lay siege to the capital a la Mariupol and wait for a surrender. The outcome of the war may turn on whether Russia is capable of doing that successfully or whether Ukrainian troops outside the city can mount the sort of counteroffensive described above to break the siege. If they can, the Russians will be faced with a scenario in which they can neither starve the Ukrainians into submission nor overpower them in combat. Maybe that’s when Fukuyama’s prediction of morale “vaporizing” comes true.

But it’s also when things would get really dangerous.