The Pendulum Swings

With jazz's transition from New Orleans to Chicago and New York, from bordellos to dance clubs, black culture assimilated into the mainstream of American popular culture. As a largely untapped and unexplored form, musicians saw in jazz an opportunity to gain financial rewards and cultural respect. However, informal and formal racial segregation stifled opportunities for black musicians to grow (in both financial and cultural aspects), while many white musicians prospered. This tension underlined much of the discourse of swing as it developed from jazz.
Formal segregation, where blacks were limited to visiting black-only venues, allowed white jazz bands (such as Austin High Gang) to rip-off black musicians' sounds and styles (Gioia 55). While this band and other all-white bands prospered for a short time on record sales, the invention of the radio changed everything (2.12. Lecture). Gone were many racial barriers; black performers gained more attention, popularity, and respect because listeners judged them on one factor: the music itself (you cannot tell the ethnicity of a performer by their music alone).
Still, this new opportunity did not end the racial tensions of the Swing Era. Duke Ellington recognized the importance of an agent who could advance his career: a white agent, Irving Mills. Where other talented musicians such as Fletcher Henderson were poised for success in the same way as Ellington, many did not see or instead opted out of having a white agent. Mills was able to get Ellington gigs at venues dominated by white audiences, better record deals, and high radio play. As a result, Ellington's band went on national tours, generating them more renown and profits from their records (2.12. Lecture). Though Fletcher Henderson was also an incredibly talented musician and big band leader, he never appreciated the same success as Ellington did, largely because he worked and performed in a segregated black community.
Ellington was criticized throughout the Swing Era, with some critics claiming that he was not being sensitive to the struggles of "his people" (2.14. Lecture). This criticism emerged during the Great Depression, and Ellington was essentially in a place of "damned if you do, damned if you don't" racial sensitivity. His music did not discuss race directly, but was rather implied in some of his song titles ("Black and Tan Fantasy", "Black Beauty").
As jazz and swing reached broad American audiences it became a more respected cultural form. However, white musician Benny Goodman is regarded as the "King of Swing", despite having challengers to that title. Goodman was the first swing musician to play Carnegie Hall in 1938, and though he hired black musicians to play in his band, the primarily white audience in attendance accredited him with being the first master of the form. Competitions between white and black swing leaders (Goodman and Chick Webb at the Savoy in 1937) further encapsulated feelings of racial tension, with Goodman "winning the competition" despite accounts that portrayed the two leaders as comparable (2.14. Lecture).