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This paper examines politics of race and gender in Russia’s new labor market that emerged amid shock therapy, privatization, and the 1998 financial crisis through the interrelation of two industries: sex and modeling. In surveying print media and documentary films about “winners and losers” in these informal economies, I read the generic image of post-socialist sex workers—“Natasha”—and the exalted image of Russia’s highest paid supermodel in the early 2000s—“Natalia” Vodianova—as a dyad that reveals the forces of capitalism behind both narratives and trades: labor exploitation, sexual and economic abuse, and debt bondage. I argue that reading Natasha and Natalia as a slippery dyadic formation (the generic “loser” and the singular “winner,” respectively), and crucially not as opposites, shows how the production of a national yet migratory femininity was critical to culturally reproducing Russia’s new capitalist economy and defining gendered structural positions within it. In betraying dehumanizing implications about indistinguishable “Slavic” bodies and the cultural and geographic inscrutability of the post-socialist world, the Natasha/Natalia dyad helps elucidate the work gendered labor performs in the West and in Russia’s post-Soviet modernization project: the brutal economic transition to free market capitalism, globalization, the proliferation of digital technologies and and the (re)racialization of New Russia.