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He may have two deadlines, actually, one artificial and the other more … organic.

The artificial deadline is May 9, when Russia celebrates V-E Day with a parade in Moscow. That parade will have extra significance this year since the country is not only at war but at war with, ahem, “Nazis” across the border. A stalemate on May 9, a day when Russia celebrates its military strength, would be hard for Putin to swallow. A retreat or defeat on May 9 would be unthinkable.

So he needs some sort of “victory.” Quickly.

That’s not just speculation from Golodryga. U.S. officials told CNN a few days ago that they have intelligence intercepts suggesting that Putin is “focused” on victory by May 9 for the parade. (“A victory parade with what troops and vehicles?” wondered one European diplomat.) That timetable isn’t just a matter of symbolism either; as the weather warms in Ukraine, the ground will soften and Russian tanks will have more trouble advancing. One former Ukrainian prime minister speculated that Russia’s shift away from Kiev towards the Donbas is designed to give Putin the sort of partial victory he craves as April turns to May. “My take is that this Plan B has a, kind of, deadline,” he said to CNN. “The deadline is the ninth of May.”

Golodryga’s also right that Putin will want to take another shot at Kiev, Odessa, and other prizes that have so far remained beyond his grasp *if* he can gain control of the Donbas. NATO chief Jens Stoltenberg warned this week that Russian forces that have withdrawn to Belarus are being rearmed and resupplied, and Jake Sullivan speculated that “if this offensive in the east proves to gain some traction, Russia could regenerate forces for additional goals, including trying to gain control of yet more territory within Ukraine.” Instead of an unmanageable advance on five axes, Russia will try to simplify by consolidating control in the east and south — and then maybe start pushing north and west.

Which brings us to the other deadline, the “organic” one. Is the Russian army capable of another major advance, or even of conquering the Donbas? At what point will their forces, eroded by Ukrainian attacks and poor morale, be at serious risk of breaking?

No one knows, but it’s all the more reason for Putin to push hard for some sort of success he can call a victory before May 9. It’s an open question how much longer they can go beyond that.

One point on which all observers agree is that time is of the essence in getting the Ukrainians the weapons they need for an offensive in the east. There’s a small window here in which Russian forces that withdrew from the north will need to be reconstituted, not yet fit for another major battle in the Donbas. (And maybe not fit at all, per O’Brien.) That’s the moment to arm Ukraine with the tanks and artillery it’s seeking so that it can deploy towards Sloviansk in the central eastern part of the country. Lawrence Freedman, a British professor of war studies, believes that’s where the next major battle will be fought as the Russians try to move south from around Kharkiv and north from Mariupol to surround Ukraine’s forces in the east and cut them off from the rest of the country.

Like O’Brien, Freedman isn’t sure that what’s left of Russia’s army has it in them to conquer the Donbas. And even if they manage it, they may not enjoy their prize:

Putin no doubt wishes to avoid being seen as a loser. It is possible that the ideas developed by the Ukrainian government for it to abandon NATO but rely instead on security guarantees might provide some consolation, but it would not be much. He is left with the worst of both worlds. He is seen as a bully but not a winner, and his battering of the very territories he claimed to care about most has reduced their attraction. Putin is not really a ‘hearts and minds’ man, and now has no hope of incorporating the Donbas into Russia with minimal fuss. For all his talk about historically close bonds, his approach has been brotherly only in the sense of Cain and Abel. Taking over the Donbas now would mean oppressing a hostile population, reconstructing shattered towns and cities, and guarding against future Ukrainian military action.

Freedman also sees the May 9 deadline as significant. Do we really think Putin would deny himself some sort of symbolic victory by that date if the offensive in the Donbas ends up also going badly? If we don’t, we’re left with an uncomfortable question: What might he plausibly do to secure that victory if his army can’t deliver it for him?

I’ll leave you with this remarkable clip of Igor Girkin, a.k.a. “Igor Strelkov,” a notorious figure from Russia’s 2014 campaign in Crimea and the Donbas. A former Russian soldier and FSB agent, Strelkov is an ardent Russian imperialist but he can’t pretend that things are going well in Ukraine. That puts him surprisingly in sync with today’s arresting AP story, “Russia’s failure to take down Kyiv was a defeat for the ages,” which describes how Russian forces in the north were “ill-prepared for Ukrainian resistance, proved incapable of adjusting to setbacks, failed to effectively combine air and land operations, misjudged Ukraine’s ability to defend its skies, and bungled basic military functions like planning and executing the movement of supplies.” Said one retired U.S. officer to the AP, with dry wit, “That’s a really bad combination if you want to conquer a country.”

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