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Henderson left the band to work with Sammy Stewart, in 1928 organized a new band called the Collegians
- By the mid 1930s he was based in Chicago, and working with Horace Henderson's band at the Circle Inn, and with pianist Jimmy Walker at the Square Deal Club
Don Redman took over this band in 1931; Henderson continued to work as the band's pianist and arranger before leaving to work for his brother
- Then, he worked with Earl "Fatha" Hines from 1937 to 1939; and from 1939 to 1940 he worked with Horace Henderson.
Although Horace worked continually, led bands, arranged, recorded, and composed into the 1980s, and although he is considered by many the more talented and skillful of the Henderson brothers, Fletcher remained more popular and accomplished more in the field