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At the age of seventeen, Bailey moved to Seattle and worked as a sheet music demonstrator at Woolworth's.
She married and divorced Ted Bailey, keeping his last name because she thought it sounded more American than Rinker.
With the help of her second husband, Benny Stafford, she became an established blues and jazz singer on the West Coast.
According to Gary Giddins ' book Bing Crosby – A Pocketful of Dreams – The Early Years 1903-1940, in 1925 she secured work for her brother, Al Rinker, and his partner Bing Crosby.
Giddins further states that Crosby first heard of Louis Armstrong and other Chicago black jazz records from Bailey's own record collection.
Crosby helped Bailey in turn by introducing her to Paul Whiteman.
She sang with Paul Whiteman's band from 1929 to 1933 ( Whiteman had a popular radio program and when Bailey debuted with her version of " Moaning Low " in 1929, public reaction was immediate, although she did not start recording with Whiteman until late 1931 ).

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