Yamshchikov examines the oeuvre of V. Popov, a living classic of the ‘Leningrad school.’ The focus of the article are his three books, an unofficial trilogy of loss, comprising the novellas Third Breath [Tretie dykhanie] (2003) and A Mosquito Lives as Long as It Sings [Komar zhivyot, poka poyot] (2006) and the novel To Dance to Death [Plyasat do smerti] (2011). Although correlating with the latest versions of European autofiction produced in the past couple of decades, Popov’s trilogy constitutes an unconventional example of autobiographical self-reflection, recorded on the ‘margins’ of the writer’s professional and private life. Unique in its contrast to Popov’s typically cheerful and optimistic oeuvre, the ‘loss trilogy’ is less of a search for new heights common in Russian autofiction in the years before the genre really took off (‘female’ optics, the essay-novel), and more of a bridge to the 2010s’ more relaxed experiments with prose — most importantly, abandonment of genre constraints and development of a free style, unrestrained by context, tradition, or genre conventions. Popov’s writing is analyzed as part of the literary process of the 2000s to the 2010s, with its relevant emphases and characteristic trends.