 Kelley was hired by the "Pittsburgh Post-Gazette" in 2018 to replace cartoonist Rob Rogers, who had been fired after conflicts with the paper's ownership, which decision has been regarded as retaliation for Rogers' criticisms of President Donald Trump.He was a Pulitzer Prize finalist in the editorial cartooning category in 1999.His cartoons have also won the National Headliner Award, the Best of The West competition, the Los Angeles Press Club award, and six first place California Newspaper Publishers Association awards.