In 1927 his canvas "Red Guards at the Winter Palace" (), also known as "Takeover of the Winter Palace" () was acquired for the permanent collection of the State Russian Museum in Leningrad. In 1927 Osmerkin took part in the major art show () at the State Russian Museum, where his works were exhibited alongside the works of Marc Chagall, David Burlyuk, Natalia Goncharova, Mikhail Larionov, Wassily Kandinsky, Robert Falk, Kuzma Petrov-Vodkin, Pyotr Konchalovsky and other masters of Russian art. At that time Osmerkin moved forward with his style, because the peak of avant-garde movements was over right after the revolution, and some trends were losing their novelty, so he embraced a classic and more traditional system of figurative and plastic imagery. He was also able to show his works at the Leningrad Academy of Arts, as well as at Leningrad Union of Artists, he also showed his works at the Leningrad Writers Club, with the help of his friends. In 1937 he made stage design for Pushkins play "Mozart and Salieri" at Bolshoi DramaTheatre. Osmerkin was a head of personal workshop at the Leningrad Academy of Art (since 1932 Institute of Painting, Sculpture, and Architecture, since 1944 Ilia Repin Institute of Painting, Sculpture, and Architecture) and was a one from founders of the Leningrad School of Painting (). He had a number of talented students in Leningrad, such as Elena Skuin, Victor Teterin, Evgenia Baykova, Lev Orekhov, Ivan Godlevsky, Gleb Savinov, Olga Bogaevskaya, Vasily Savitsky, Evsey Moiseenko and other artists. Osmerkin, as a highly original artist who contributed to development of the Russian avant-garde, risked to suffer from the Soviet officialdom under Joseph Stalin. He saw the destruction of private art collections, even some museums and libraries. Osmerkin survived the first wave of persecution of Russian intellectuals. He was emotionally devastated by the arrest and execution of his friend Osip Mandelstam. During the 1940s and 1950s Osmerkin enjoyed a continuous friendship with poet Anna Akhmatova. In 1946, the Soviet Communist Party started attacks on some intellectuals and creative artists. Along with other victims of such attacks, such as Anna Akhmatova and Mikhail Zoshchenko, Osmerkin was accused of formalism, and spreading western influence to Soviet art.