Five years on, however, Akimov is one of the staunchest opponents of Moscow’s rule. Amid economic stagnation and a mounting crackdown on political dissent, a sense of buyer’s remorse is creeping into Crimea, with Akimov’s about-face only one of the most visible examples. And as Moscow moves to formally absorb Abkhazia and South Ossetia, the territories it annexed from Georgia a decade ago, and to recognize Transnistria, another Kremlin-backed breakaway region wedged between Moldova and Ukraine, as a fully fledged state, the Crimean experience sounds a warning that realities of life under Russia may not be all that Putin promised.

Russia's seizure is making former Soviet states nervous

Akimov, who describes himself as “a businessman,” has turned his efforts to lobbying for a second vote on Crimea’s future. In the original referendum, results showed that 95.5 percent of voters supported rule from Moscow, though at least 10 percent of the population boycotted the poll in protest at the takeover. Akimov told me he believes that should the referendum be run again, and run fairly, the split would now be about 50–50.

“There will be a referendum, maybe in one year, or maybe in 100 years. But it will definitely happen,” he said.

An imminent rerun, which would depend on Russia’s acquiescence, is unlikely, however—and that delay in a vote could have profound consequences for the results of any future referendum.

According to some estimates, Crimea’s population has increased 25 percent since 2014, mostly due to an influx of military and state personnel from Russia who are, by definition, pro-Russian. In the same period, about 140,000 Crimeans, 9 percent of the 2014 population, have left the peninsula for the Ukrainian mainland. Many of them are members of the Muslim Tatar minority, who mostly opposed annexation and have since been targeted in a Russian clampdown. Should these trends continue, demography will decide Crimea’s future.

Nonetheless, Akimov is turning his hand from a paramilitary organization to political leadership in a last-ditch attempt to turn the tide. He has taken his Cossack militia into an alliance with the Communist Party of Russia for the upcoming Crimean parliamentary elections in September—an unlikely coalition, he conceded, given that the Communists support the annexation. A small lockup that used to house a museum of Cossack history is now the nerve center of his political operation. Pale patches on the smoke-tinted walls mark where the exhibits of Cossack costumes and posters once hung, and on Akimov’s desk are piles of Spark of Truth, the Communist Party’s newspaper, which features a sketch of Joseph Stalin on its masthead.

While it is highly improbable that Akimov can lead Crimea back out of Russia, Moscow has noted his change of heart. Akimov said he can no longer walk through the square where he cheered for the Kremlin’s Crimean takeover five years ago without being intercepted by Russian security agents. In 2016, he organized the first protest against Russian rule, for which he said he was detained for three days. He has been taken to court eight times since then, and warned not to meddle in Crimea’s politics. The day after we met, he called to say that he’d had yet another visit from the police.