Olinsky came to America in 1891 with his family. His father had been a farmer in Russia. He studied at the National Academy of Design under Weir and Vonnoh (1893-98) and at the Art Students League with Bryson Burroughs. He worked as an assistant to John La Farge on window and mural commissions in New York, Boston and Washington, D.C. (1900-08). In 1904 he married Genevieve A. Karfunkle, the sister of a fellow student at the Academy. They travelled in Italy and France (1908-11).
Upon their return to New York, Olinsky set up his studio in Greenwich Village, began showing at Macbeth Gallery, and began teaching at the National Academy of Design. Olinsky first came to Old Lyme in the summer of 1917 and in 1919 purchased the home he had been renting there. A few years later he added a studio. He remained a summer resident of Old Lyme until his death.
Olinsky taught at the National Academy until his death, at the Art Students League 1928-34 and 1944-62, and at the Grand Central School of Art. He also exhibited at Grand Central Art Galleries.
Olinsky specialized in portraiture and still life. He painted in a style consonant with his academic training, yet in his landscapes the influences of impressionism can be found.
