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Bertrand was born in Biloxi, Mississippi and was active on the Chicago blues/jazz scene of the 1920s. Bertrand recorded with Louis Armstrong, Johnny Dodds, Tampa Red, Ma Rainey, Freddie Keppard, Erskine Tate, Big Bill Broonzy, Doc Cook, Jimmy Blythe, Lee Collins, and Blind Blake amongst many others. In addition he led Jimmy Bertrand's Washboard Wizards.