… the maximal nature of Russia’s goals – conquest and regime change – impose considerable challenges all on their own. Russian troops will need not only to seize the country but also hold it and support the administration of whatever government Putin puts in place, against what is likely to be intense popular resistance. They will also need to take Ukraine’s major cities, particularly Kyiv. Urban warfare is brutally difficult and has in the past not been a particular strength of the Russian Federation.
That does not mean Ukrainian resistance is pointless here. Instead, both the initial, conventional stage of resistance and the likely secondary insurgency phase push towards the same objectives: making Russian occupation so costly in blood and treasure that it cannot be maintained. Here the Ukrainians have a real chance of eventual success if they remain committed to the effort, while the challenges for Russia are immense. Consider the US experience: Ukraine is about 10% more populous and about a third larger than Iraq. Whereas the funds for Iraqi insurgents often had to come via limited dark money or relatively weak state sponsors (like Iran) Ukrainian resistance, meanwhile, is likely to be bankrolled and supplied by the richest countries in the world able to use the traditional banking and finance system to do it (either covertly or overtly) and move those supplies through transport routes in well-developed NATO countries whose airspace is effectively inviolate. And finally, Russia has less than half of the United States’ population and about a sixth of the US’ economic production (adjusted for purchasing power). The United States in Iraq also had allies, both in the region and also providing troops; Russia has no real allies in this fight, though China may seek to keep Russia from becoming entirely economically isolated.
Russia is thus embarking, with fewer friends and fewer resources, on a war that may prove to be far more difficult than the wars the United States struggled with in Afghanistan and Iraq. And of course the very fact that Ukraine can win this in the long run will serve to stiffen Ukrainian resistance. Meanwhile, it is not entirely clear that Putin’s war has widespread popular support in Russia, though of course getting any clear sense of the popular mood within an authoritarian state is extremely difficult. Nevertheless, flagging public support at home, even in an authoritarian state where there are no political channels for that opposition, can translate into morale problems at the front, as Russians learned in 1917.
Maybe not impossible, but very hard:
(source)