[2][4] He received his education from Alabama State College and then attended Howard University where he studied under Alain Locke, Sterling Brown and James A.

Bailey was described as taking pills then drinking, spending his money on "a full pint of scotch" or vodka.

[5] While living in Atlanta he created posters for the H. Rap Brown Center, a venue that was frequented by members of the Student Nonviolent Coordinating Committee (SNCC).

[8][9] After the Six-Day War, which Israel won, SNCC launched an anti-Zionist campaign featuring anti-Semitic images.

Bailey created an illustration featuring an Israeli firing squad shooting a group of Arabs with a caption reading: "This is the Gaza Strip, Palestine, not Dachau, Germany".

[11][12] The Palestine Problem, another comic by Bailey during this time, connects United States racial violence, military imperialism in Vietnam and the Arab world, and the Afro-Arab freedom struggle.

[11] According to the Los Angeles Times, his graphic of a white hand holding a Star of David with a dollar sign, which was tightening the nooses around the necks of an African-American and an Arab man, was used in an infographic by Harvard Palestinian solidarity activists in February 2024.

[13] James Early cites Kofi's work as a major influence, describing the illustrations by Bailey as "among the great, energizing artistic expressions created in the crucible of social justice activism and organizing that was Atlanta in the 1960s."