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‘Dear Russians,’ anti-separatist Vladimir Simperovich, above, wrote early in the conflict. ‘Please do not tell me what's going on Donetsk. I am in Donetsk.’

‘Dear Russians,’ anti-separatist Vladimir Simperovich, above, wrote early in the conflict. ‘Please do not tell me what’s going on Donetsk. I am in Donetsk.’

Anton Skyba/for The Globe and Mail

When an outspoken young man vanishes amid turmoil in the former Ukrainian region he calls home, The Globe's Mark MacKinnon embarks on a risky journey to find out what happened to his friend

He looked thinner, and was dressed all in black even though he had previously favoured bright colours. His hair, always short, was now in a military-style crewcut. He walked with a limp, leaning slightly on his umbrella as we approached our designated meeting point – a bust of the poet Alexander Pushkin in the middle of a pedestrian boulevard in Donetsk – from opposite directions.

This is how my friend Vlad appeared, two years after I'd seen him last, and 16 months after he had seemed to disappear from the face of the Earth.

His round face broke into a smile as we neared each other, and he extended a hand. "It's so good to see you," he said with a command of English that had once made him Ukraine's high-school debating champion in the language. I took his hand and pulled him into a hug, relief overwhelming all the precautions we had taken in setting up our meeting in the tense and isolated mini-state that broke away from Ukraine two years ago, sending Vlad's life into a terrifying tailspin.

Pulling back from our embrace, I asked him how he was. Fat snowflakes fell lazily around us on a chilly mid-March morning.

He exhaled before answering. "I'm not okay, but at least I'm alive."

It's a common sentiment in the Donetsk People's Republic, a twilight zone that is neither Russia nor Ukraine, but a land in-between, where it feels as if the Soviet Union has somehow been resurrected.

And the Soviet Union was never pleasant to those who disagreed with its rulers.

'Dear Russians, please do not tell me …'

The first time I met Vladimir Simperovich was in April, 2014. Ukraine had just experienced a pro-Western revolution, one that Donbass, his native region, was railing against. Groups of pro-Russian fighters had seized control of key buildings in the main cities of Donetsk and Lugansk, as well as several nearby towns. After a surreal referendum the following month, stage-managed by the Kremlin – which was furious about the developments in Kiev – the men with guns would declare themselves the government of separate "people's republics" for Donetsk and Lugansk that together encompassed a few thousand square kilometres between the Russian border and the Ukrainian army's new front lines.

Most of those I met in Donetsk that spring seemed willing to go along with what was happening. They repeated the narrative fed to them by Russian television: "Fascists" had taken over in Kiev, toppling the elected pro-Moscow government led by Donetsk native Viktor Yanukovych. Independence or, better yet, absorption into Russia had to be preferable to life in this new "nazi" Ukraine.

Or maybe they had come to the quiet realization that it was better to agree with the people holding the guns.

Not Vlad. Scanning my Twitter feed one night while I was in Donetsk, I came across an account written by a local resident who was openly critical of what was happening, albeit from behind a screen of online anonymity as @VoiceofDonetsk. He bitterly mocked the referendum, and cheered Ukrainian army advances (sometimes going so far as to celebrate separatist deaths – not uncommon in the angry social-media war being fought alongside the real one).

"Dear Russians," Vlad wrote early in the conflict, "please do not tell me what's going on in Donetsk. I am in Donetsk and can see things better from here than you can from Moscow."

Intrigued by the author's fearlessness, I arranged to meet him at a little yellow-walled bakery called Donbass Bread, not far from my hotel.

Donetsk then was still largely unscarred by the nascent conflict, the city's emerging prosperity a reminder of all that would be lost if the region followed the dimly lit trail stretched out before it.

Artema Street, the city's main commercial drag, featured Western brands such as Zara, Mango, Adidas and Calvin Klein. Not far away were Ramada and Park Inn hotels built for the 2012 European soccer championships (Donetsk was one of eight host cities). There was a brand-new airport, a world-class soccer stadium, as well as a modern ice rink where HC Donbass, Ukraine's lone member of the Kontinental Hockey League, played its home games. There was an impressive opera house, a bustling McDonald's, and an emerging karaoke culture.

I had visited the city a decade earlier – when it was far less developed, but even then a bastion of resistance to Ukraine's first pro-Western revolution in 2004 – and was impressed by the changes made since (Donetsk residents, like their neighbours across the border in Russia, enjoy Western products far more than they like Western politics).

When we met, Vlad seemed flattered to be interviewed by a foreign correspondent, but despondent over what was happening to his city and region. Then 27, he told me that he'd started his blog and Twitter account in order to "fight against Russian propaganda."

The conflict in Donbass, he said, was neither a Ukrainian civil war nor a full-on Russian invasion. Vlad saw it the way many Ukrainians did: as a cynical contest for command over the region's coal mines and steel mills. "Our local elites want to control the financial sources in Donetsk. They want to be able to steal money in the same amounts as before the revolution," was the crux of his analysis.

He said he was worried Donetsk would end up like Trans-Dniestr, a breakaway region of neighbouring Moldova controlled by Russian-supported separatists since a 1990 war there. I suggested that would be a grim fate. I had briefly visited Trans-Dniestr, and spent most of my trip worrying that the secret police – unreformed Soviet KGB – were monitoring me and those I met. The economy of Trans-Dniestr remains almost non-existent after more than two decades of "independence."

The interview ended with the two of us cheerfully tussling over who would pay for the coffee. He eventually let me win.

We shook hands and promised to meet again. Then Vlad asked his stepbrother – who had joined us, but said little – to take a photograph of us in front of the café. It shows Vlad wearing a pink dress shirt with his sunglasses tucked into the neck. I've got a blue shirt on, a pen sticking out of the breast pocket.

Only later, when Vlad, unabashedly proud of our new friendship, posted the photo online and made it his profile picture on VKontakte – the Russian equivalent of Facebook – did I wonder if the photo was a smart idea.

'Don't speak English!'

The next time I heard from Vlad was a month later, in May, 2014. I was on a train from the eastern Ukrainian city of Kharkiv, headed back to Donetsk when my phone rang.

"Where are you right now?" he asked with none of his previous mirth. When I told him, he became agitated.

"Exactly which wagon are you in?" he asked. Sounding upset, he told me he would meet me on the platform.

Vlad grabbed me by the elbow as soon as I stepped off the train. "Don't speak English!" he whispered fiercely in Russian. "People are looking for you!"

We walked briskly to a waiting car and sped away. Switching to English so that the driver couldn't understand, Vlad told me he had seen my picture on a VKontakte group used by pro-Russian activists in the city. Someone was claiming I was a CIA agent, he said, and there was talk of kidnapping me, along with another Western journalist (who turned out not to be in Donetsk at the time), so they could exchange us for comrades who had been captured by the Ukrainian army.

Worryingly, what he was saying sounded plausible. Two days earlier, I had been covering a pro-Russian demonstration in the bitterly divided city of Kharkiv, and had taken a photograph of the protest, from the top of a nearby building, that illustrated how small the crowd was relative to the massive plaza they were gathered on.

Immediately, pro-Russian Twitter accounts started claiming that I was a foreign agent sent to undermine and ridicule the "Novorossiya" – "New Russia" – project they were hoping to spread from Donetsk to Kharkiv. At the time, I chuckled at the online nonsense and continued my work.

But the look on Vlad's face convinced me I needed to be concerned now. I was in Donetsk, the airport was closed, and the train station was apparently full of people looking for me. After driving around the city for a while, we decided that the Park Inn, where many other Western journalists were staying, including several long-time friends of mine, was the safest place for me to be.

Vlad stayed for dinner, and despite the dangers – or maybe because of them – he downed one beer after another. Soon, he was telling me and two colleagues a horror story about how he'd been detained earlier that year for helping a foreign journalist, and held for three days and nights in the basement of the separatists' headquarters in the centre of Donetsk. (Many journalists hire "fixers" – local guides and translators – when reporting from a place they're unfamiliar with. I never hired Vlad as a fixer, or paid him for any of our meetings.)

Vlad told us how he had been handcuffed to a pipe and beaten. Our jaws dropped as he related the details. My colleagues and I debated whether we should write about what he was telling us. Vlad said he wasn't afraid of what would happen to him, but we were. We didn't want to put him in any more danger than he already was.

But Vlad instinctively charged toward trouble. As we finished our meal, he became irritated with a trio of Russian journalists who were talking and laughing loudly as they consumed a late-night bottle of vodka.

"I can't stand it," Vlad said. He walked over to ask the Russians what they thought was so funny about the war their country had brought to his city. A fistfight – one a stumbling, drunk Vlad would have been very unlikely to win – was narrowly avoided.

'Blessed With Coal'

My worries about Vlad escalated a few months later. I was travelling back to Donetsk, and hoped to meet him, but discovered that both his phone numbers had been switched off. His social-media accounts were also uncharacteristically quiet (after writing a barrage of anti-separatist rants following the downing of Malaysian Airlines Flight MH17, with all evidence pointing to a missile fired from territory controlled by the Donetsk People's Republic). I sent him a series of increasingly concerned notes and, after what seemed like an eternity, he finally replied.

He was living with his grandparents in Ugledar, a town recently retaken by the Ukrainian army. He said he was safe, and working on a new project, which he described as "helping to evacuate women and children from Donetsk and nearby cities." Mobile reception was poor in Ugledar – and WiFi non-existent – but he was soon back tweeting full-bore, mocking the Kremlin and those who worked for it in Ukraine.

The name Ugledar means "Blessed With Coal," and during the Soviet era it was indeed a blessing. The coal brought factories, along with an influx of Russian workers and their families, to this part of what was then Soviet Ukraine. The region's industrial base meant both relative affluence, and something of an exemption from the Holodomor, the great famine, that Joseph Stalin inflicted on the agriculture-based centre and west of the country.

But Donbass has been in free fall since the end of the Soviet Union. As Ukraine opened its economy to the West, the region's coal mines and metallurgical factories became increasingly obsolete. The population of Ugledar shrank from more than 20,000 in the Soviet era to barely 15,000 at the start of the current war.

Even before the revolution in Kiev, many in Donbass seemed to long for a leap back in time. Nostalgia for the Soviet era grew continuously, manifesting itself each Ukrainian election in lopsided votes in favour of pro-Moscow politicians like Mr. Yanukovych, though bribery and other types of electoral fraud probably played a role in that.

When Mr. Yanukovych was ousted in February, 2014, much of Donbass watched in confusion. They weren't necessarily happy with life under the corrupt rule of Mr. Yanukovych and his cronies, but they were far from sure that greater integration with the European Union, the key demand of the protesters in Kiev, would work to their benefit.

When armed separatists started taking over government buildings that April, Ugledar was one of the towns they seized first. The local population took part in the May referendum, and – according to the separatists' count – voted overwhelmingly to be part of the Donetsk People's Republic.

Ugledar was recaptured that August, as the overstretched separatists withdrew to more defensible lines around the cities of Donetsk and Lugansk, but Soviet thinking still lingers across the region.

A poll in January financed by the Canadian government found that only one in five Donbass residents (only those living outside the separatist-controlled areas were asked) would choose a democratic government over a prosperous economy. Another poll result that set the region apart from the rest of Ukraine: Most respondents favoured joining a Moscow-led customs union over greater integration with the EU.

Vlad and I arranged to meet on my return to Donetsk in November, 2014, but his phones were again off when I arrived. I didn't worry at first, even when the occasional "Where is he?" tweet – posted by concerned followers of his blog – crossed my screen. I assumed Vlad was back incommunicado in Ugledar.

But when the weeks of silence became months, I started to fret, recalling his sometimes foolhardy bravery, as well as his stint in the dungeon of the Donetsk secret police. I sent a string of messages to his e-mail addresses, as well as his Facebook, Twitter and VKontakte accounts.

Months passed without any reply. Eventually, I tried reaching out to his Facebook friends, asking when they'd seen him last. Only one replied. "I don't know what to think," wrote a former classmate who said she hadn't seen or heard from Vlad for a long time. "All I know is that he was helping refugees."

Then Vlad's VKontakte account – where he had posted the photo of the two of us outside the bakery in Donetsk – was deleted. It was as though someone was erasing all traces of his existence. A pro-Russian Twitter account suggested that Vlad had been kidnapped.

An alarming Twitter post, accompanied by the photo of Vladimir, left, and Mark MacKinnon taken when they first met.

An alarming Twitter post, accompanied by the photo of Vladimir, left, and Mark MacKinnon taken when they first met.

I returned to Ukraine in February, 2015, and dialed his number, hoping to end the mystery. It wasn't Vlad who answered. "We don't know the person you're asking for," said a man, speaking gruffly in Russian. He hung up when I asked him to identify himself.

My heart sank, even though I had no way of knowing at the time that Vlad had once more been arrested by the police of the Donetsk People's Republic.

Cursed by Chernobyl

Vlad was born with a reason to hate the Soviet Union, and to sneer at those who felt nostalgia for it.

His father, also named Vladimir, was drafted into the Red Army, where he served as a mechanic and was assigned to a base near Kiev. He was working there on April 26, 1986, when Reactor No. 4 at the nearby Chernobyl nuclear plant exploded. Vlad's father spent the next few months cleaning and repairing the military vehicles coming and going from the exclusion zone.

He developed leukemia, and by November of the same year, Vlad Sr. was dead, at the age of 19. His only son was born three days later.

Vlad's mother, Svetlana, worked at a hospital in Donetsk. She would have another son six years later, but was left to raise the boys alone when the father of her second child left the family and moved to Kiev.

Although they were Russian-speakers in a heavily Russified region, a place where most around them longed for the stability of the Soviet days, Vlad grew up a Ukrainian patriot. He travelled twice to Kiev during the protests that eventually ousted Mr. Yanukovych, and joined a Ukrainian unity rally on March 6, 2014, on Donetsk's central Lenin Square.

The Lenin Square gathering was a last-ditch effort to stop events that were already in motion (by then, armed separatists had seized control of the main regional government building), and an estimated 10,000 pro-Ukrainian activists turned out. There was brief optimism that those working to hold the country together would prevail over those trying to pull it apart.

A week later, pro-Russian activists staged a counterdemonstration, on the square, that descended into a street brawl. A pro-Ukrainian protester, Dmytro Cherniavsky, was stabbed to death in the fracas.

It was the first death of the war for Donbass. More than 8,000 people have died since.

'Are you kidding me?'

I decided in March of this year that the only way to find out what had happened to Vlad was to return to Ukraine and look for him myself.

A short stopover in Kiev offered reasons for pessimism. The consensus among the diplomats and aid workers I met, as well as former residents of Donetsk and Lugansk, was that anyone who had gone silent as long as Vlad was likely in prison, or dead.

Especially if he had been outspoken about his pro-Ukrainian views.

I visited Maria Varfolomeeva, a journalist who had spent more than a year in captivity in the Lugansk People's Republic, hoping for clues as to how the separatists might deal with someone like Vlad. Ms. Varfolomeeva, who was accused of being a spy for the Ukrainian government because she filmed outside a residential building that turned out to be a separatist military barracks, laughed bitterly when I asked if Vlad might have put himself in danger by criticizing the separatists on his blog and Twitter. "Are you kidding me?"

Amnesty International researcher Krassimir Yankov said that stories like Maria's and Vlad's had become increasingly common in the separatist-controlled areas of Ukraine. The leadership of the unrecognized Donetsk and Lugansk statelets appeared to be "going after well-known 'enemies of the republic,'" in recent months, perhaps to distract from the economic problems in their regions, Mr. Yankov said.

He warned that looking for a single missing person – like Vlad – in that part of Ukraine was like "looking for a needle in a haystack. Nobody really knows what's going on in Donetsk."

But I had to try. I decided to travel to Ugledar, where Vlad had been, the last time he'd gone silent.

Mark MacKinnon first flew to Kharkiv, about 400 kilometres east of Kiev, rented a car and headed south to Ugledar in Ukrainian territory, hoping to find Vlad there, safe with his grandparents. After a stop in Kramatorsk for documents, he had to spend the night in Druzhkivka (the new home of Donetsk's hockey team) after mangled roads hobbled his car. He was about to pass Krasnoarmiisk when Vlad's brother, Bogdan, called and arranged to meet him there. The news Vlad was alive but confined to Donetsk required a return to Slavyansk and a second overnight stay, before a border crossing at Kurakhove and a much-anticipated reunion in the separatist capital.

Mark MacKinnon first flew to Kharkiv, about 400 kilometres east of Kiev, rented a car and headed south to Ugledar in Ukrainian territory, hoping to find Vlad there, safe with his grandparents. After a stop in Kramatorsk for documents, he had to spend the night in Druzhkivka (the new home of Donetsk’s hockey team) after mangled roads hobbled his car. He was about to pass Krasnoarmiisk when Vlad’s brother, Bogdan, called and arranged to meet him there. The news Vlad was alive but confined to Donetsk required a return to Slavyansk and a second overnight stay, before a border crossing at Kurakhove and a much-anticipated reunion in the separatist capital.

I never reached Ugledar

Travelling through eastern Ukraine in early 2016 is a journey through a war on pause. There is something like a ceasefire holding around the front line, but neither side believes the conflict is really over.

Under what's known as the Minsk peace process – named after the Belarusian capital where it was negotiated – both sides have pulled their heavy artillery and rocket launchers 30 kilometres back from the front. But every night, there is a cacophony of small-arms fire, and the occasional mortar round, as the two armies continue to probe each other's defences.

Driving on the Ukrainian side of the line, a planned 340-kilometre trip from Kharkiv to Ugledar became a two-day odyssey. The roads, always poorly maintained, have been torn up into a jagged mess by tanks streaming to a civil war no Ukrainian ever expected to fight.

The potholes were so deep that the battered Lada I was riding in managed to blow not one, but two tires, badly bending both rims and necessitating an overnight stop and a car swap. The next day's trek was slowed by a succession of sandbagged military checkpoints, where Kalashnikov-toting Ukrainian soldiers stared with interest at my Canadian passport.

I never reached Ugledar. On the second day of the drive, I unexpectedly received a text message informing me that a mobile number Vlad had once called me from was suddenly active again. (In Ukraine, if you call a number and it's out of service, the operator will send you a text message when that number is back on the network.) I dialled it anxiously, fully expecting to hear another stranger's voice. But this time, Vlad's half-brother, Bogdan, answered.

Bogdan had been with Vlad when we met for the first time. He took the picture of us standing outside Donbass Bread. He remembered me.

"He's okay," Bogdan answered cautiously, when I asked about his brother. "He's in Donetsk."

Questions whizzed through my mind – if he's okay, why didn't Vlad answer any of the dozens of messages I'd sent over the past 16 months?

Bogdan agreed to meet me in Krasnoarmiisk, another town briefly captured by the separatists back in 2014, but now behind Ukrainian lines. Bogdan's life, like many with roots in Donetsk and Lugansk, now straddles both sides of the unofficial border. He studies economics in Krasnoarmiisk, on the Ukrainian side, but his home and family are in the Donetsk People's Republic.

He was fidgety when we met, and clearly unsure what he was supposed to tell me about Vlad's whereabouts. He agreed to tell Vlad that I'd been scouring eastern Ukraine for him, and had feared – until reaching Bogdan – the worst. Bogdan admitted that the picture he took had "caused some trouble" for his brother.

Vlad called me that evening, breaking 16 months of silence.

"I have some troubles here in Donetsk with the police and so on," Vlad explained vaguely. He told me he'd had his passport seized, and couldn't leave the Donetsk People's Republic. But if I could get to Donetsk, he would be happy to see me again.

The next day, I hired a driver to take me across the front line.

Vlad had helped me once when I was in danger. I figured I owed him one.

Empty pallets show what the stadium that once housed Donetsk’s professional soccer team is now used for: a distribution centre for food aid.

Empty pallets show what the stadium that once housed Donetsk’s professional soccer team is now used for: a distribution centre for food aid.


A shadow of its pre-war self

The two-kilometre stretch of no man's land between the last Ukrainian military checkpoint and the first line of separatist defences bears the scars of the hotter days of this war. As we drove between the front lines, we passed a pair of electricity towers that had somehow been bent in half. Next came the ruins of a white minibus that had edged off the road in February and hit a landmine, killing four people. Then an abandoned plant that once produced sunflower oil for Cargill, the U.S. food giant.

The fluttering black, blue and red flag of the Donetsk People's Republic marked the first separatist checkpoint. Five fighters in fatigues, cradling Kalashnikovs, emerged from a log-and-cement foxhole that was built in 2014, but could just as easily have existed in 1914. One looked briefly at my passport and press card before waving us on.

Next came the customs office of the unrecognized statelet: a metal shed in front of a burnt-out gas station. As another man in camouflage gear registered the entry of our beige Chevy Aveo, my eyes wandered over freshly dug trenches, a symbol of how this once fast-moving war has entered a longer and much more drawn-out phase.

Finally we reached Donetsk, a city now a shadow of its prewar self.

The Western brands were the first to flee, leaving a row of boarded-up storefronts along Artema Street. The advertising market has unsurprisingly crashed, and most views in the city are scarred by empty metal billboards. The only active advertiser is the separatist government itself, which has erected dozens of signs reminding residents to celebrate Soviet-era holidays. One poster on Artema featured Stalin, chin up, over the slogan: "Victory will be ours!"

But while the Kremlin may have gained several strategic objectives by supporting the separatists – most notably by smashing talk that Ukraine might join Western institutions such as the EU or NATO any time soon – it doesn't feel like the people of Donetsk are winning anything.

Donbass Arena, the soccer stadium the city was so proud of in 2012, was hit during the Ukrainian army's sometimes indiscriminate shelling. Its undamaged parts now function as a distribution centre for the humanitarian aid that arrives in controversial convoys from Russia (the 50th such convoy arrived just before my visit in March). The airport, scene of the heaviest fighting to date, is a shattered mess.

The Ramada and Park Inn hotels have somehow kept functioning, although their business models have been turned upside down. Credit cards and bank machines stopped working early in the conflict, as Donetsk and Lugansk were cut off from the international financial system. The separatists threw businesses another curve ball last year when they declared that the Russian ruble, rather than the Ukrainian hryvnia, would be the lone currency allowed in the now cash-only economy. Nightlife is curbed by a 10 o'clock curfew. Donbass Bread, where Vlad and I first met, is boarded up.

On March 16, the Donetsk People's Republic took the symbolic step of issuing its first passports. Alexander Zakharchenko – prime minister of the unrecognized state – was the lead recipient, followed by dozens of Donetsk residents who had turned 18 since the war began, meaning they had no other travel documents.

They were the first official citizens of this republic no one recognizes, the teenagers' new passports a confirmation of their status as hostages of the conflict.

A Ukrainian passport can still get you through the checkpoints that separate Donetsk and Lugansk from the rest of the country (provided the Ukrainian side doesn't suspect you of fighting for the separatists), or across the Russian border. But passport-holders of the Donetsk People's Republic – or those, like Vlad, who don't have documents at all – can't go east or west. Their world is confined to the handful of cities and towns the separatists control.

I decided to spend some time watching the generation that may grow up knowing no other state but the Donetsk People's Republic. The "sports palace" near my hotel was packed on a Saturday morning with children and preteens performing astounding feats on the tumbling mats and parallel bars. Above them hung a trio of flags: the Russian tricolour, the blue-black-red of the Donetsk People's Republic, and the blue cross on red background that is the banner of the "Novorossiya" project.

Later that day, the city would hold its amateur-boxing championship. For Donetsk athletes, it might as well have been the Olympic Games. "They can't go anywhere higher than this," Sergei Akhmetov, vice-president of the city's boxing federation, told me. "Maybe some competitions in Russia, but the European and world championships are not for us."

He was interrupted by one of his boxing coaches, clearly frustrated with his boss's overly polite description of the situation. "We are hostages here!" shouted a balding man with a mouthful of gold teeth. "Why does Canada recognize the revolution in Kiev, but not ours?" he continued at top volume. Then his comments slid into a stream of hatred directed at the West, replete with racism and anti-Semitism.

Derelict billboards in Donetsk: All the turmoil has blighted a once-vibrant (and Western-oriented) economy in a city that Vlad now describes as a big ‘prison.’

Derelict billboards in Donetsk: All the turmoil has blighted a once-vibrant (and Western-oriented) economy in a city that Vlad now describes as a big ‘prison.’


'It's like a big prison'

The real fighting around Donetsk has picked up again recently. The Minsk agreements, which somewhat stabilized the situation for the past year, seem to be crumbling, with both sides accusing the other of failing to implement its terms.

Monitors from the Organization for Security and Co-operation in Europe say the separatists and the Ukrainian army have both started seizing ground in what was once the no man's land between the front lines. "The armies are getting closer to each other. This is causing increased tension," said one monitor, who spoke to me on condition of anonymity.

When I stayed at the Park Inn in the fall of 2014, my nights were sleepless as the city shook with artillery shells landing on or near the city's devastated airport. This time, I was awoken only once by the sounds of heavy machine-gun fire somewhere in the distance.

"It's like a big prison," Vlad began as I pulled out my notebook in a quiet corner of a coffee shop not far from the Pushkin statue where we had met that chilly Saturday afternoon in 2014. Before choosing a place to talk, we walked aimlessly for a while, trying to make sure we were not being closely followed.

I ordered a cappuccino. He had a black coffee. As proof of how worried I was, I pulled out a printed photo of him that I'd been planning to show around Ugledar before I heard from his brother.

Vlad smiled sadly. He didn't apologize for my worry. But he explained.

As the separatists tightened their control over Donetsk and Lugansk in 2014, he had shifted from online dissent to a mix of more active opposition and humanitarian work. He set up an account for donations from Ukrainians who wanted to help those still living in the rebel-held areas, and used the money to buy warm clothing and medicines that were starting to become scarce in the unrecognized republics. (It was better, he suggested to readers of his blog, that aid to Donetsk come from Ukrainians – otherwise residents would be forced to rely on the humanitarian convoys from Russia, a huge propaganda win for Moscow.)

With a friend, he also started arranging travel documents for those who wanted to leave. Vlad was spending most of his time outside the separatist-controlled areas, and used his contacts to help renew expired passports on the Ukrainian side. The new passports he brought back were effectively a ticket out of Donetsk for those who preferred to live in the government-run part of Ukraine.

Eventually, his efforts drew the attention of the Donetsk authorities. In February, 2015, he received a request from a woman who said she wanted his help getting her passport renewed. Unbeknownst to Vlad, her husband worked for the separatist government as a police officer, and their meeting was photographed.

Vlad was arrested afterward, and his mobile phone seized with all his e-mail and social-media accounts open for the officers to read. He would have been in deep trouble then and there, except for the fact that they were mostly in English, which the police officers couldn't understand. He convinced them he was writing satire – and thus was conceivably pro-government – but knew he had to stop blogging and tweeting, since he was no longer anonymous.

Released with a warning to stop his passport trade, he quickly returned to the safety of Ugledar, on the Ukrainian side of the line. His mother – who needed to stay in Donetsk; her salary from the hospital where she had worked her whole life was now supporting the entire family – begged him to end his online war against the separatists, and he agreed.

He had fooled the regular police, but knew the MGB – the separatist secret police, reportedly led by retired KGB agents – would not be amused when they read the file. Vlad stopped using the e-mail and social-media accounts that had been open on his smartphone when the police seized it. He never saw my increasingly worried appeals for a reply.

He also might never have returned to Donetsk, had his grandmother not fallen ill, and needed surgery, a few months later. His mother arranged for expedited medical attention, and Vlad travelled with his grandmother from Ugledar to Donetsk last August.

The surgery was successful, but Vlad was awakened at 7 the following morning by pounding on his door. The police had found out he was back. And by now they knew exactly what kind of blogger he was.

"They didn't say anything to me, just that I had to go with them. Then they put my hands behind my back and put handcuffs on me," Vlad told me. He was put in a car and driven to a police station, where he was asked to sign a statement confessing that he had been trying to cheat people by taking money for travel documents he couldn't deliver.

Vlad says he charged just enough to cover his costs. The only person to offer more than that had been the police officer's wife. (Vlad believes one reason for the sting operation was to eliminate competition, since the separatists were offering a parallel service for several times the price.)

"They kept saying that I had committed a crime and had to sign this statement," Vlad said. "I refused, of course."

We ordered a second round of coffee, but by this point I was worried about whether we should keep talking. The café was becoming more crowded, and an emotional Vlad was struggling to keep his voice down as he told his tale.

He spent 72 days in prison, an experience that wasn't as unpleasant as he had expected. The guards were rough and the food was "not for humans, it was for pigs." But his fellow inmates were not what he had expected and feared. In today's Donetsk, it's often the intellectuals – rather than the hardened criminals – who end up on the wrong side of the law.

"At first I was afraid. But a lot of the people who are in prison today are good people who were arrested because they did something small." Because they were seen as opponents of the regime.

Eventually, Vlad's lawyer – an old friend with contacts inside the separatist regime – cut a deal. Vlad would be allowed out of prison, but the secret police would keep the SIM cards for both mobile phones he was carrying at the time of his arrest and, critically, hold onto his passport. He was free, but his world was now confined to the territory of the Donetsk People's Republic. (He also left with that limp, having been hit by a car outside police headquarters. Vlad doesn't believe it was an accident.)

Without a passport, he couldn't pass through separatist military checkpoints. Nor could he legally hold a job. Most of his friends had left Donetsk. But he was not the only one the separatists were holding in painful limbo. "A lot of people are in the same position of me now. They have no documents, so they can't get out to Ukraine or to Russia. They are in a prison," he told me with a bitter laugh.

A pair of men in leather jackets entered the coffee shop and took a table too close to us for comfort. We paid our bill and headed back out onto the snowy boulevard.

It struck me that one of Vlad's early predictions – that Donetsk would end up like Trans-Dniestr – had come true. The city was now just as isolated and paranoid as that other pro-Russian ministate. I recalled my day in the Trans-Dniestrian capital of Tiraspol a decade earlier, and how I had arranged a meeting with one of its few remaining dissidents. My source and I agreed that he would sit on a bench in a public park. If his newspaper was open when I approached, it would be okay to talk. If not, I was to keep walking.

The Donetsk of 2016 felt like Tiraspol in 2003. Or, for that matter, East Berlin or Moscow a few decades before.

Vlad and I strolled slowly past a series of children's playgrounds that sat empty on a Saturday afternoon. "My mother says the DPR is a republic for pensioners," Vlad commented. "Pensioners live very well. They collect one pension here in rubles, and then go to the other side and collect another one in Ukrainian hryvnia. So, of course, they support the Donetsk People's Republic."

But most young people – those not making money as fighters – have left, and little beside the pension system works. As we walked, Vlad listed off the names of factories that had closed since the outbreak of war two years before.

I asked him what he did with his spare time.

He used to relax by going to the park across Artema Street from his house, but stopped after someone – he can't fathom who or why – uprooted most of its greenery. "Our people have even stolen the trees from the park," he said. The words "our people" came out dripping with disgust.

He related how he and his prewar girlfriend – with family roots in Russia – had broken up in large part because they disagreed so vehemently about what was happening in Donetsk. He said he had not spoken to his only cousin, who worked for the separatist government, since the war began.

Vlad said he had recently taken up boxing. It seemed an odd hobby for someone who had struck me as a burgeoning, if combative, intellectual when we first met. But the intervening two years had clearly hardened him.

We parted for the afternoon, agreeing to meet up again for a precurfew drink that evening. My intention was not to interview Vlad again, but to give him what must have been a rare night off, to help him unwind, if only for a few hours. I wanted to see the cheerful young man I had met two years before.

It proved impossible. Shouting over 1990s Britney Spears songs and a plate of french fries at a bar in the city centre, I tried talking about soccer and hockey, but every conversation inevitably led back to politics and to Vlad's precarious situation. Shakhtar Donetsk, the city's beloved soccer team, was still one of Ukraine's best, but now plays its home games in the western city of Lviv. The city's ice palace was looted and set ablaze in May, 2014 – HC Donbass has relocated to the Ukrainian-controlled town of Druzhkivka, and no longer plays in the KHL.

I tried asking about movies, but Vlad hadn't seen any recently. He grumpily pointed out that the only films showing in local cinemas were ones stolen from the Internet.

The bar was crowded, but Vlad couldn't keep his voice down. "There's no future here," he said several times, too loudly for my liking. "If I could leave this place, I would never come back."

We parted, promising to stay in closer touch from now on. But I left Donetsk the next day feeling as if I was abandoning my friend to a rather unpleasant fate.

The Ukrainian border checkpoint at Kurakhove: Travel to and from the breakaway republic of Donetsk is restricted and closely supervised.

The Ukrainian border checkpoint at Kurakhove: Travel to and from the breakaway republic of Donetsk is restricted and closely supervised.


'I was very nervous'

The idea to rescue Vlad wasn't mine.

A mutual friend called a few days after I left Ukraine. He said he had found a way to get Vlad out of Donetsk, if someone was willing to put up the money. He had made contact with a network of smugglers who made their living driving back and forth across the front line, "tipping" soldiers on both sides not to look inside their vehicles.

One of the smugglers was claiming they could drive a person across the front as easily as any other contraband. They were asking for $400 (U.S.) for the whole operation.

I hesitated. No laws would be broken, since the border Vlad would be taken across was one no country in the world – not even Russia – recognizes, but this was clearly a dangerous endeavour. In my imagination, the smuggler would be using some poorly guarded back road, one where the fighting could flare up at any minute, potentially putting Vlad in the line of fire.

Paying for Vlad to escape was also against all the rules I'd been taught long ago at Carleton University's School of Journalism. Journalists are supposed to maintain objectivity at all times. We're only to observe – and never get involved in – the stories we report.

But Vlad and I had affected each others' lives since the moment I'd first come across his Twitter account. To pretend I'd had no impact on him, and played no role in creating the situation he was trapped in, felt ridiculous. I told the mutual friend that, if Vlad was willing to take the risk, I would pay the $400 from my own pocket.

Vlad indicated he was, indeed, desperate enough to trust a smuggler. "I hope it will happen soon," he wrote me by e-mail in early April.

Two weeks later, the right combination of soldiers – those who knew not to look in the smuggler's car – were in position on both sides of the front line. At 4 o'clock on a weekday morning, Vlad bade his mother goodbye, and got into a sedan that pulled up outside his apartment. The driver was a man, as Vlad expected, but there was also a young woman in the back seat. Nobody spoke.

After a short drive, they reached the separatist front lines. The driver got out of the car. Vlad could see three armed men, but studiously avoided eye contact with them. "I was very nervous. I knew that, if they asked for my documents, there would be a big problem, and I would never have another opportunity to leave."

The driver came back a few minutes later and wordlessly set off again. Next came a Ukrainian checkpoint where, after a longer wait, the driver again arranged for his two passengers to cross without showing any documentation.

Vlad exhaled as they left the war zone behind. He was dropped at the first bus station on the Ukrainian side of the line – he headed straight back to his grandparents' place in Ugledar – while the young woman stayed in the car with the driver. Vlad says he has no idea what ultimately happened her, or even why she was in the smuggler's car. Neither wanted to know the other's story, or to share their own.

"As soon as I passed through the checkpoints, I began to feel free. The sky is bluer here than it was in Donetsk. The trees are more green," Vlad recounted with a wide smile when we met again, this time in a Kiev pub. Six weeks had passed since we'd last seen each other.

Over a table laden with cheese and beer – "there's no good beer in Donetsk," he declared with a wide smile as he sipped a pint of Czech lager – I asked him what he thought he'd do next.

Top of his mind was getting a new passport, something he was unhappy to discover would require paying another bribe. "Nothing has changed," he said, referring to Ukraine as a whole. This spring, a tranche of reformist cabinet ministers left the government, complaining that President Petro Poroshenko and his allies aren't serious about combatting the corruption that has plagued the state – and provoked successive waves of protest – since the Soviet era.

Next up on Vlad's to-do list was restarting his Twitter account. The separatists and their allies in the Kremlin would again be the target of @VoiceofDonetsk, but Vlad also plans to take on the problems he sees around him in "free" Ukraine. It bothered him that the Ukrainian soldiers had taken money not to look in a smuggler's car that night. He pointed out that it could just as easily have been stuffed with explosives.

Vladimir Simperovich plans to drop the anonymity this time around. He wants everybody to know his name. He has dreams of becoming a respected political analyst and pundit.

"I'm not afraid any more," he said as we soaked up a sunny late-April afternoon in Kiev. "Now I can write as Voice of Donetsk and show my personality, and say yes when people ask to interview me. It's kind of a new life."

It looked like it. Just nine days after he'd escaped his open-air "prison," I noticed Vlad was again dressing and acting like the young man I had first met two years earlier. He was wearing an unbuttoned grey sweater over a white "Tokyo Tigers" T-shirt. He had sunglasses tucked into his hair, which had grown out of the crew cut he was sporting when we met in March. A pair of black earphones dangled from his slightly thicker neck. Over three meals we shared during the day our travels overlapped in Kiev, Vlad rarely stopped smiling.

The only time his mood dipped was when I asked if he thought he'd ever return to Donetsk.

"Donetsk was a good city. I used to think it was one of the greatest cites in Ukraine," he began.

Now, he knows, he'll almost certainly never go back. Even if the war were to end tomorrow, Vlad says he wouldn't feel safe in Donetsk "until Lenin is removed from the central square and the Ukrainian flag flies there."

Those things are unlikely to happen any time soon.

He can still see his mother when she travels to Ugledar, but he may never again see his home, or his local park, or Artema Street, or the bust of Alexander Pushkin where we had met so nervously just a few weeks before.

"Donetsk, for me, is a dead city," Vlad pronounced.

His voice softened as he said it, as if he were mourning a friend – one more casualty of the strange war in eastern Ukraine.

Mark MacKinnon is The Globe and Mail's senior international correspondent, based in London.

TIMELINE: The Vladimir adventure from start to finish

The Backdrop

November, 2013
Protests begin in Kiev, and Vladimir Simperovich comes to take part.

February 21, 2014
President Yanukovych flees to Russia .

March, 2014
Russia annexes Crimea.

April, 2014
Armed pro-Russians declare Donetsk and Lugansk separate "people's republics." Mr. Simperovich uses Twitter to criticize them and their supporters.

The Meeting

April, 2014
Intrigued by his Voice of Donetsk posts on Twitter, Globe reporter Mark MacKinnon arranges to interview Mr. Simperovich.

May, 2014
He returns to Donetsk, and Mr. Simperovich helps him avoid an apparent kidnap plot.

July 17, 2014
Malaysian Airlines Flight MH17 is shot down over separatist-held Ukrainian territory, killing 298.

The Silence

November, 2014
Mr. Simperovich goes silent after being arrested. He is released, but warned to stop blogging.

August, 2015
He has crossed into Ukraine to live with his grandparents in Ugledar, but returns to take his ailing grandmother to hospital, and is arrested again.

October, 2015
Upon his release, his passport and telephone SIM cards are kept. He can no longer leave Donetsk.

The Reunion

March, 2016
Worried by his friend's prolonged silence, Mr. MacKinnon returns to Ukraine to look for him, travelling to Donetsk.

April, 2016
Two years after their first meeting, Mr. MacKinnon agrees to help The Voice of Donetsk escape from Donetsk.


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