No event has done more to spook the Kremlin over the last decade than the Orange Revolution in Ukraine in 2004. Now Vladimir Putin’s worst moment looks like turning into a recurring nightmare as demonstrators once again fill Kiev’s Independence Square, demanding that their country move closer to the European Union (EU) and further away from Russia.

The demonstrations in Ukraine are both a humiliation and a threat to Putin. While the Russian president may laud the deep cultural and historical ties between Ukraine and Russia, he is discovering that tens of thousands of Ukrainians would prefer to brave freezing temperatures and flying truncheons rather than be drawn closer into the Russian sphere of influence.

What is more, if a popular uprising can once again threaten to topple a corrupt and intermittently despotic government in Ukraine, then the potential lesson for Russia is clear. After all, it is less than two years ago that demonstrators filled the streets of Moscow to protest against the Putin restoration and to label his United Russia party as the “party of crooks and thieves”.

A pro-EU uprising in Ukraine also threatens President Putin’s vision for Russia in the world. His main foreign-policy goal is the construction of a sphere of influence for Russia, covering most of the old Soviet Union. Ukraine — with its 45 million people, large territory, economic resources and long-standing links to Russia — is meant to be the jewel in the crown. It matters far more than Moldova or Belarus. If the Ukrainians turn West, not East, Putin’s foreign policy is in tatters.

And yet the Russian government has only itself to blame for this turn of events. It has set up a crude tug-of-war with the EU over the fate of its neighbour, while forgetting the obvious lesson of the original Orange Revolution - that if you try to settle the future of Ukraine, over the heads of its people, they can take to the streets in numbers so massive that they can change the political direction of their nation.

In an effort to persuade Ukraine to look to Moscow, not Brussels, the Russians approached the Viktor Yanukovich government with cash in one hand and a cosh in the other. Over the summer, trade restrictions were placed on Ukrainian goods to make the point that the country could expect to pay a heavy price if it turned its back on Russia. At the same time the Russians made a direct appeal to the financial interests of Ukraine — and, more pertinently, of the Ukrainian elite.

Two recent meetings between Putin and President Yanukovich seem to have been decisive in persuading the Ukrainian leader that his interests — and those of his family and close associates — lay in siding with Moscow. Proximity to power is often a route to wealth in Ukraine. The president’s son, Alexander, who trained as a dentist, is now a very rich and well-connected businessman.

The moment when the Ukrainian leader announced that he would not be signing an association agreement with the EU, it must have felt like a sweet victory in Moscow. But the triumph has been shortlived. Even if Yanukovich’s thuggish police manage to bludgeon the opposition into silence, the Ukrainian government will be gravely wounded — and the whole idea of a Eurasian Union will be damaged.

Putin may have miscalculated because he believed his own propaganda about the Orange Revolution. In his view, far from being a genuine popular uprising, it was an event manufactured by western intelligence agencies, using US and EU-funded non-governmental organisations as their tools. For Putin, the so-called “colour revolutions” were doubly sinister. First, they threatened to pull nations out of the natural Russian sphere of influence and into the orbit of the West. Second, they may serve as a template for similar uprisings in Russia itself. Indeed, when demonstrations broke out against dubious elections in Russia in the winter of 2011-12, Kremlin’s reaction was to crack down on the western NGOs that it alleged were stirring things up.

The idea that a popular revolt could be genuinely popular — rather than the product of a behind-the-scenes manipulation — seems to be one that the Putin government finds hard to grasp. (In some ways this is surprising, given Russia’s own history — although perhaps not so surprising, considering the role that conspiracy played in the Bolsheviks’ seizure of power in October 1917.)

This limited and conspiratorial view of the original colour revolutions may have made Moscow vulnerable to another unpleasant surprise on the streets of Ukraine, as ordinary people have moved to undo deals made over their heads by leaders they regard as corrupt and illegitimate.

As a Russian nationalist, Putin likes to argue that Russia is a unique “civilisation” — distinct from that of Europe. As a result, the struggle for Ukraine is, for him, not just about wealth or power politics — it is civilisational. The notion that the Ukrainian middle-class, at least in the capital city and the more developed western half of the country, feels more attracted to the civilisations of Warsaw, Berlin and London — rather than Moscow — is offensive to Russian nationalists in the Kremlin and beyond.

Yet, in reality, the prospect of Ukraine drawing closer to the rest of Europe — and becoming wealthier and better-governed in the process — will ultimately be in the interests of Russia. It may serve as a template for the future development of Russia itself. But, for that very reason, events in Ukraine are profoundly threatening to the personal interests and ideology of Putin and his circle.

— Financial Times