That 40-year-old Sergei Gerdjuk is still alive today is almost miraculous given that 13 years ago he was a drug addict and serial thief. Then he found faith, and was able to turn his life around: As part of this rebirth, he has long desired to obtain Estonian citizenship. But this path has been riddled with bizarre obstacles.

Sergei would like to get citizenship as he not only lives in Estonia but is also a so-called gray passport-holder, a person who does not hold the citizenship of any country – the state issues travel documents of this color to such persons.
However, he finds some of the barriers to doing so, which include his criminal past, to be unfair.

"I want to draw attention to how our country treats people who have a past like mine. I consider that unfair. Many people reform themselves, start families and businesses, yet they are not granted citizenship, as they once did something wrong," Sergei told "Pealtnägija."

Currently living in the Mustamäe district of Tallinn, Sergei grew up in a single-parent household with his mother, but ended up on a criminal path as a teenager. He was using drugs at 13, while by the time he was 28, he already had 11 criminal and 25 misdemeanor convictions to his name.

"I had never worked. I had many fines owed to the state. I had an eighth-grade education. In the family setting I acted in a way that made them less than happy to see me. Every time I was released, I was received with anxiety," Sergei recounted.

Having served multiple prison sentences and used drugs even while incarcerated, in 2012 Sergei came to realize that he had to make changes. He now sees quitting drugs as the key turning point, and he now counsels young people struggling with similar addictions.

Once sober and out of jail, he explored religious teachings and completed the schooling he had left unfinished. "I felt like I was disabled. When the court asked about my education, I always lied, saying that I had finished nine grades, though in reality it was eight, and not even those completed. I went back to 9th grade to feel more confident if someone in court should ask me again. Then later on I got to like it, and completed up to 12th grade," he said.

That struggle, mostly with himself, has lasted for 13 years now. Over this time, Sergei has acquired vocational training, set up his own construction company, and made new friends.

"I've been watching him for many years and the steps he has taken. He only moves forward. He moves almost too briskly forward. Exams, studies, a company… just amazing," said one acquaintance, Ljubov Pljato.

Yet his major struggles now are in the pursuit of getting citizenship, generally encouraged by the Estonian state.

However, someone with a criminal record can only obtain that citizenship via a special decision of the government, which has its own rules. Sergei ticked these boxes: He waited 10 years for his criminal record to be expunged, passed the citizenship and language tests, and applied for Estonian citizenship in 2022, but, to his surprise, was still denied.

"This is unpleasant, rather than insulting. I am aware of my past. There are things there that are not very pleasant, but that doesn't reflect the current state of things. We all change, and in my opinion, they should meet me halfway," Sergei went on.

Ministry of the Interior adviser Siiri Leskov shed some light on practices.

"When it comes to people with criminal convictions, the government has more or less agreed on a best practice: For lighter crimes, once the punishment is served, three years must elapse after the record is archived before we even start to consider the exceptions. Next, we assess whether that is enough time to vet a person's law-abiding behavior. With somewhat more serious crimes, this period comes five years after archiving. For the most serious crimes, at least seven years, or even more," Leskov said.

In short, Sergei applied too early. He had thought a former criminal could apply for citizenship a decade after his last sentence expired, but in fact, he needed to wait another three years on top of that.

In Sergei's view, this decision as signed by the prime minister was unfair, all the more so since no law mentions the three-year rule — it is only an administrative best practice. He therefore sued the state, and won, though even then the court did not say that he must be granted citizenship as mandatory, merely that the state had not adequately justified its decision and had ignored Sergei's transformed lifestyle.

However, the ruling did force the state to reconsider its stance.

"The court cannot say whether the decision was right or wrong. The court cannot give the government that kind of substantive assessment. It can only examine whether the decision was sufficiently reasoned, and whether all procedural norms were followed," Leskov explained.

"I thought that if I won in court, the court would say that I must get citizenship, not that I have to go through the same process again with the same people who in my opinion have judged me unfairly, and who again have the decision-making power," Sergei meanwhile said.

The Police and Border Guard Board (PPA) reassessed the situation, but again issued a refusal. This time, what weighed against him was that, despite his apparent whiter-than-white persona nowadays, he had been caught over more recent years speeding, running red lights, using his phone while driving — incidents even visible via his own social media.

The registries did not display these, but the citizenship application process pulled in that information.

The most serious incident, however, involved his Staffordshire bull terrier, Dasha. In June 2024, the dog broke free from its leash and rushed an approaching corgi.

"The leash broke. I ran to keep them apart. I know she isn't aggressive, but many people cross the street when they see her. The other dog owner panicked. Instead of rescuing his own dog, he started filming things with his phone. I told him to help, but he kept filming," Sergei explained.

The ensuing dogfight was replicated by the human owners, ending up with Sergei kicking the other man — which the latter caught on film.

A criminal case was opened for causing bodily harm, though later terminated through an out-of-court plea deal.

"I went to the prosecutor's office and they told me they had discussed it and wanted to offer me this option: We won't take it to court, you can just pay for the repair of a phone screen that broke when it fell, and cover the procedural costs for the work done. That went into the state coffers. Altogether it came to about €900," Sergei explained of his penalty.

However, Leskov said that Sergei had implicitly accepted culpability with the deal.

"We specifically look at facts. If he accepted the opportunity, then he admitted the act. If he had been innocent, he would not have agreed to this termination, would have gone to court, and the truth would have come out," Leskov explained

While he achieved at best a Pyrrhic victory in the court, at a time when he should have been flawless, Sergei had unfortunately fallen into some new troubles, now has to forget about any dreams of citizenship, for at least three years. Not even citizenship by exemption is on the cards now, she noted.

"Citizenship by exemption can only be granted when the criminal record has been archived, the person's character allows for it, and likewise, so does the nature of the crimes. If later, say within a year, a person repeatedly runs red lights or speeds, then we cannot say that he is now law-abiding," Leskov noted.

Estonia is also granting an exemption to gray passport holders, who number in the tens of thousands, as a demographic, ahead of next month's local elections. While Russian, Belarusian, and other third-country (non-EU) citizens have lost the right to vote in the locals, gray passport holders have not, at least this time around. They are to be encouraged to take citizenship between now and the next local elections in 2029, by which time gray passport holders will not be able to vote either.

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