Like most figures who have undergone significant transformations in the public eye, Ksenia Sobchak, the most prominent candidate running against Vladimir Putin in Russia’s presidential election Sunday, means different things to different people. Her detractors see a campy celebrity-turned-politician—a puppet who is merely playing the role of substantive challenger. Her supporters, on the other hand, see a skillful operator capable of effectively manipulating the media—a new kind of political personality putting forth an alternative vision for the country.

Just a decade ago, she was known exclusively as a socialite and entertainer. Despite coming from a political family, she had launched her career as a television personality, appearing in reality shows and also providing political commentary for Russian state media, before branching out into entrepreneurial activities, including clothing and footwear design. A svelte, well-coiffed and well-heeled blonde, Sobchak marketed herself domestically and internationally as the ideal version of Russian womanhood, parlaying her youth, beauty and connections into cover shoots for magazines like Russian Elle, InStyle and Glamour as well as an extensive social media following. ...