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He adopted the name of Jean Gilbert for the production of his first operetta Das Jungfernstift in 1901. He continued to work as a Kapellmeister at the Berlin Apollo-Theater [de] on Friedrichstraße, where he conducted operettas by Paul Lincke. In 1908, Gilbert moved to Düsseldorf and again turned to composing. Back in Berlin by 1910, he composed more than 50 operettas before and after World War I. His most successful work was Die keusche Susanne (1910), which was also popular in an English adaptation as The Girl in the Taxi.
As a Jew, Gilbert was forced to leave Germany after the Nazi seizure of power in January 1933. He first emigrated to Madrid and later to Argentina, where he once again worked as a radio orchestra leader. He died in Buenos Aires. His elder son Robert Gilbert (1899–1978) was also a composer, his younger son Henry Winterfeld (1901–1990) became a well-known author of books for young readers.