 In 1936 he went to Chicago in search of work, and got a break as soloist on trombone for Benny Goodman's big band.He also worked with the Jack Hylton orchestra and then with the Casa Loma Orchestra (led by Glen Gray) from 1937-1941.In 1941 McEachern joined the Paul Whiteman orchestra and shortly after began entertaining U.S. troops during World War II.