Alisher Usmanov is nicknamed "the hard man of Russia," but he's good at seducing the softies in California's tech community: An investment firm he backs lead a $180 million investment in Zynga, the gaming company that trafficked in scammy ads.

The investment firm, Russia's Digital Sky Technologies, led a broader group of investors in putting money into San Francisco-based Zynga, according to the New York Times. It's DST's second Silicon Valley conquest, following two investments in Facebook earlier this year that totaled $300 million and that allowed the social network to cash out employee equity.

Usmanov (pictured), who reportedly owns 32 percent of DST, comes with the sort of unsavory press clippings worthy of a long-survivng oligarch in anarchic, organized-crime-ridden Russia: He's been accused by a former British ambassador of being a "gangster and racketeer" and of close ties to mafia drug trafficking and, as we've reported previously, controversially tried to censor bloggers who linked to news of the accusations.

Then there was this, last year: After Usmanov bought a chunk of mobile phone operator Megafon through a holding company and from a fund called IPOC, a former Megafon shareholder said he had been physically coerced into selling his Megafon holdings to IPOC; he later disappeared from his bloodstained vacation home in Latvia.

Zynga is used to dealing in the dark fringes of the markets; it made loads of ad revenue off scammers who deceptively sold "learning CD" and SMS subscriptions to gamers trying to earn virtual currency and now faces a class action lawsuit. Now, despite all the company's talk about reforming its way back into the light, it is, in a way, going deeper into the shadows. Zynga CEO Mark Pincus once bragged about "doing every horrible thing just to get revenues right away." Let's hope, for his sake, he's not making such a recklessly calculated move now.