 In 1929, he began writing articles and drawing cartoons and caricatures of famous people appearing in the news for the "New York Times".These appeared in the political and theater pages as well as their "Sunday Magazine".Since the "New York Times" and the "Chattanooga Times" were both owned by Chattanoogan Adolph Ochs, Leo was given the opportunity to work simultaneously on the staff of the "Chattanooga Times" where he interviewed, wrote and illustrated a column entitled "Chattanoogans in Gotham".