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Viktor Yanukovich, the last Moscow-friendly Ukrainian president, was toppled by protests in 2014 and fled to Russia, and Petro Poroshenko, his successor, has put fierce opposition to Moscow at the heart of his re-election campaign.
Challenger Yulia Tymoshenko, third in the polls behind Poroshenko, calls Russia an “aggressor country”. And Volodymyr Zelenskiy, a TV comedian leading the polls, says the two countries are at war and wants Ukraine to join the EU.
Meanwhile Yuriy Boyko, a former ally of ousted Russia-friendly president Yanukovich, is trailing in fourth. While he has courted voters with promises to reverse unpopular heating tariff increases, he is unlikely to win.
Part of Russia’s Ukraine problem is rooted in arithmetic.
Many voters in annexed Crimea and separatist-held eastern Ukraine, an area with a combined population of around 6 million people, according to data published by the separatists, are unlikely to take part in the election as they need to undergo a special registration process on Ukraine-controlled territory.
A further 3 million Ukrainians who live and work in Russia will not be able to vote either.
Moscow’s 2014 actions mean it has lost almost all influence in the parts of Ukraine it does not control, giving it few options to shape events. Kiev says Russia is using cyber efforts to try to disrupt the election to undermine its legitimacy, a charge that Moscow denies.
“Poroshenko is obviously impossible for us to deal with,” said one source familiar with Kremlin thinking, who said a Poroshenko win would entrench a political stalemate between Moscow and Kiev.
Although Poroshenko was Moscow’s worst case scenario, other candidates were a write-off for Russia too, the source said.
A second source close to the Kremlin agreed that a Poroshenko win was Moscow’s least favoured outcome, but said other candidates, notably Tymoshenko, at least offered a faint hope that the two countries could start talking again.
The source noted Tymoshenko had experience of dealing with Russia in gas price negotiations when she was Ukrainian prime minister and might be more pragmatic.