Dave Whamond's cartoon titled 'The Man who would be king' captures a caricatured Donald Trump donned in regal themes, complete with crown and red robe, wielding a scepter. A subservient, bald figure with pointy ears bows and praises the 'Great Halloween Costume, Boss!' while Trump retorts 'What Halloween Costume?' The image tags highlight themes of No Kings, Trump wants kinglike powers, and concerns over constitution and democracy. It satirizes ideas of president transitioning government into a monarchy, with elements of shutdown, taking control, and totalitarian state. The humor lies in Trump playing dress up yet denying it's a costume, symbolizing real aspirations for kinglike authority.
On October 16 2025 a political cartoon by Bruce Plante depicts three children on a suburban sidewalk during Halloween night. A child in a Donald Trump costume sits on the pavement with candy spilled from a bag after an apparent fall. A child dressed as Frankenstein stands nearby and says the Trump costume was a bad idea while another child in a witch costume runs away. The scene references ongoing political perceptions of Trump around the 2025 period.
In a cartoon published September 29 2025 two girls converse in a sandbox about Halloween plans. The child on the right states she wanted to dress as a clown but her parents feared Trump would take it personally. The background includes playground equipment and greenery under a clear sky. The image references ongoing political tensions around the former and potential future president. Artist Christopher Weyant signed the work for the Boston Globe.
On October 23 2024 Rick McKee depicts Donald Trump dressed in a military uniform covered with dictator references and medals. A child in a ghost costume approaches and comments on the outfit while Trump questions whether it is a costume. The scene references recent remarks attributed to Trump about Hitler and his day one dictator statement during the 2024 campaign.
