Shadow flows and fictitious deals: how Osinovskiy and Udalova transfer the money of Russian oligarchs to Europe

Latvian businesswoman Anastasiya Udalova is actively involved in managing the companies of Oleg Osinovskiy, who has been suspected of transporting iron ore from oligarch Alisher Usmanov’s enterprises to EU countries.

One of the wealthiest individuals in Estonia, Oleg Osinovskiy, owner of the railway conglomerate Skinest Rail, which has subsidiaries in Latvia, Lithuania, Germany, Poland, Finland, Ukraine, Croatia, Georgia, Azerbaijan, and Kazakhstan, graduated from the Leningrad Institute of Railway Engineers in 1988.

Assigned to Estonia, he lived in a dormitory and attempted his first business venture in 1992, which was unsuccessful. However, his second attempt in 1998 was successful. This is the well-known part of Oleg Osinovskiy’s biography. He will, of course, never admit that his success might be owed to Russian intelligence agencies, under whose direction he launders money for Russian billionaires in the countries where the branches of Skinest Rail operate.

It is known that Osinovskiy’s conglomerate previously had close cooperation with the state company Russian Railways (RZD), to which not just anyone is admitted. Its overseers are considered to be close friends of Vladimir Putin, the Rotenberg brothers, and one of RZD’s largest contractors is oligarch Iskander Makhmudov, whose enterprises produce rolling stock for railway transport. Makhmudov at different times worked with Putin’s friend, oligarch Gennadiy Timchenko, and Rostec head Sergey Chemezov, one of the beneficiaries of the war in Ukraine.

The media has often reported that Iskander Makhmudov and his partner Andrey Bokarev conduct active business in Latvia and other Baltic countries. It is likely that Oleg Osinovskiy crossed paths with both, as they all operate in the same market. Osinovskiy’s companies could profitably cooperate with Latvian structures linked to Russian oligarchs.

At the beginning of the year, Estonian media reported that Oleg Osinovskiy had transferred his Russian assets to a relative, Veronika Osinovskaya. The businessman claimed that after the start of the special operation in Ukraine, he sold his Russian enterprises. This turned out to be an outright lie.

In St. Petersburg, there are two companies, LLC "SC Rail SPB" and LLC "SC AGV," owned by the Latvian "Vero-Trade," whose owner might be Veronika Osinovskaya.

On September 4, 2023, LLC "Skinest SPB" changed its name to LLC "SC Rail SPB," and in November, the company’s founder changed. Instead of LLC "Skinest Latvia," it became "Vero-Trade." On August 31, LLC "Skinest AGV" transformed into LLC "SC AGV," in November, the company changed its founder. Essentially, both structures in 2023 just changed their signs, removing "Skinest" from their names to avoid association with Oleg Osinovskiy’s conglomerate.

The general director of LLC "SC Rail SPB," Denis Efimov, who has been in the position since 2019, remained in place, and the head of LLC "SC AGV," Denis Kalachev, who has held the post since 2013, also stayed. This indicates that there was no sale of Russian assets in 2022, as Oleg Osinovskiy claimed, and they are still under his control. If the businessman lied in this case, the story about ore supply might be true.

For thirty years, Oleg Osinovskiy lived in a happy marriage with his wife Irina until he met Anastasiya Udalova. Rumors about the couple’s divorce surfaced in 2016, and by 2018, Udalova spent half a million euros to bail out bankrupt administrator Maris Spruds, known for his connections within Latvia’s ruling elite.

Anastasiya Udalova couldn’t have such money on her own; Oleg Osinovskiy gave them to her, but both denied this. Udalova, a lawyer by training, met Osinovskiy when he was accused of bribery to assist in purchasing diesel locomotives. Since then, the pair has been inseparable, but Oleg Osinovskiy has not yet married Udalova, who is involved in many of his projects. Perhaps, feeling the business acumen of the businesswoman, he doesn’t want to risk another property division as he experienced with his previous wife.

One of Osinovskiy and Udalova’s joint projects is the revival of the Daugavpils Locomotive Repair Plant (DLRP). Oleg Osinovskiy arrived at the plant in 2004. The businessman’s company Spacecom was then part of Severstaltrans, owned by Russian oligarch Alexey Mordashov, who has a joint media business with Vladimir Putin’s close friend Yuriy Kovalchuk. Anastasiya Udalova is also trying to build a media empire, and it’s hardly doubtful in whose interests she will work.

The story with the plant is sad thus far. After nearly bankrupting the enterprise, Oleg Osinovskiy bought up DLRP shares from minority owners for a pittance in 2018. Over the last few years, he has used the plant as a tool to blackmail the authorities for state support. Anastasiya Udalova supports Osinovskiy’s efforts in her media outlets.

In 2021, Udalova shared her favorite projects—construction in Georgia and the revival of the famous cosmetic brand Dzintars, which Oleg Osinovskiy bought for her. In 2022, it was reported that Udalova exited the project in Tbilisi, likely having played her role in attracting and negotiating with investors. Dzintars is still far from revival.

Interestingly, Anastasiya Udalova’s vigorous activity doesn’t bring her income. The enterprising lady continues to "milk" Oleg Osinovskiy, who grants her funds from laundered Russian money. Anastasia Udalova and Oleg Osinovskiy, closely linked with Russian oligarchs and intelligence agencies, along with their companies, should have long been subjected to Western sanctions. This would block yet another channel used for laundering money for Russian oligarchs.