When Michael S. Steele announced his candidacy for the U.S. Senate election of 2006, Gilliard mocked Steele's perceived subservience to the Republican Party by posting a photoshopped picture of Steele in minstrel makeup (see Blackface). This was picked up by Jeff Jacoby, a columnist with the "Boston Globe", who was so incensed by Gilliard's comments about Black Americans that he dedicated a column criticizing him in December 2005. Gilliard reproduced the relevant portion of Jacoby's column on his own website, along with a copy of the response he had emailed to Jacoby, in which he said that he and most other blacks held black conservatives "in complete and utter contempt".