Pollock worked as a booking agent for several clubs starting in the late 1910s before becoming an executive with the Havana Red Sox/Cuban House of David/Pollock's Cuban Stars from 1927 to 1933.

[19] Pollock's booking agency scheduled games for the Zulu Cannibal Giants in 1935, a club that featured shirtless players who wore only grass skirts.

[20] By 1936, he was the booking agent for the barnstorming Miami Giants, who were renamed the Ethiopian Clowns, with Pollock having forged a partnership with owner Hunter Campbell after loading him money.

[26] The team, which at various points would be referred to as the Ethiopian, Cincinnati and Miami Clowns, joined the Negro American League for the 1943 season.

Pollock received criticism from some fellow baseball executives and members of the media for the Clowns' presentation and on-the-field actions.

[34] Smith also levied criticism in 1942 and 1943 against the slapstick comedy routines the team performed, the use of the Clown monikers, coupled with the painting of players' faces, and accused Pollock of profiting off racist stereotypes of indigenous Africans.

[24][35] That same year, Homestead Grays owner Cumberland Posey said that while he liked Pollock personally, he criticized his use of "Ethiopia" in the team's name, accusing him of capitalizing on the Second Italo-Ethiopian War, an event closely followed in Black newspapers.

[24] On June 25, 1944, the Clowns walked off the field in the seventh inning of the second game of a double-header against the Memphis Red Sox following a disputed call from an umpire.