Chaika was central to the fusing of Russian organized crime and the siloviki, which has resulted in a kind of nationalization of extortion, racketeering, and other targeted violence. A thorough profile in the independent Russian news site Meduza alleges that Chaika’s ties to organized crime in Russia go back decades to when he was a prosecutor in eastern Siberia in the early 1990s. It was the era of privatizing the Soviet economy, and it was often violent, especially in Siberia. While Chaika spoke often about fighting “bandits,” the ones who operated in the areas he was responsible for were often mysteriously escaping prosecution. At the end of the decade, he came under scrutiny himself for two things: In one case, he was under government investigation for accepting a gold Longine watch worth thousands of dollars as a bribe, and in the second, $1 million of the money he asked the government to allot to build a local law school disappeared. (When a local newspaper reported on the government’s investigation, according to Meduza, their offices were raided by the special police, who planted pornography on the editor in chief. Chaika has never denied the substance of the profile; after other newspapers reported on the story, the police backed off the local editor.)
Chaika’s name continues to appear in some of contemporary Russian history’s least flattering moments. According to a profile in the liberal Russian New Times magazine, which Chaika also appears not to have disputed, when the prisoners of a Siberian prison rioted in 1979, Chaika, a young prosecutor at the time, allegedly brought them drugs in exchange for confessions. When in 1999 Vladimir Putin, then head of the FSB, took out one of his main impediments to getting the Russian presidency with kompromat—a tape of a man who looked like then-prosecutor general Yury Skuratov frolicking with prostitutes—Chaika was happy to go along and move the criminal case against Skuratov, his former boss, forward. During Putin’s first presidential term, Chaika headed the Ministry of Justice and oversaw the neutralization of political parties. Any group hoping to be an official political party in Russia needs to register with the Ministry, which can and does deny registration for parties that could possibly be a threat to Putin. Under Chaika’s leadership, the Ministry helped remove potentially problematic figures from ballots in regional elections across the country.
This is the man who made an oblique appearance in emails to Trump Jr. Natalia Veselnitskaya, the lawyer who conducted the meeting with Trump Jr., Jared Kushner, and Paul Manafort in Trump Tower last summer, is very close with the Chaika family, having gone to law school with the Chaika’s oldest son, Artem, according to a source familiar with the parties involved. And when Navalny’s expose of the Chaika family’s dealings broke, it was none other than Aras Agalarov—a Russian businessman and one of Russia’s richest men— who defended the Chaika family in a column in Russia’s biggest newspaper. Aras Agalarov is the person to whom Chaika, according to Trump Jr.’s emails, offered potentially damaging information on Clinton. And it’s Agalarov’s son, middling Russian pop star Emin Agalarov, who is also mentioned in the emails, and who was acquainted with the Trumps through his family’s role in setting up the Miss Universe pageant in Moscow in 2013.