During Wednesday’s “Late Show” monologue, Stephen Colbert took aim at President Donald Trump’s comments following his meeting with Canadian Prime Minister Mark Carney. Trump stated that the main concession he sought from Canada was “friendship,” a statement Colbert found ripe for mockery. The comedian likened Trump’s plea to a desperate robber seeking compliments mid-heist, emphasizing the bizarre contrast between Trump’s international behavior and his personal longing for camaraderie.
Trump’s Vague Promises and Giuliani’s Soccer Role Spark Colbert’s Comic Comparisons
Colbert continued to poke fun at Trump’s cryptic tease about a “very big announcement” during the meeting, which he failed to elaborate on. The late-night host joked that Trump’s vagueness sounded like someone who hadn’t yet planned for Mother’s Day, drawing laughs from the audience. The punchline underscored Trump’s frequent use of grand statements lacking substance, a recurring theme Colbert has often targeted.

Shifting topics, Colbert turned his attention to the historic selection of Robert Prevost as the first American Pope, comparing the Vatican conclave to the upcoming 2026 World Cup, which will be held in the United States. He then criticized Trump’s appointment of Andrew Giuliani, son of Rudy Giuliani, to lead the U.S. World Cup Task Force. Colbert quipped that if a Giuliani was necessary, Rudy would be a better fit—if only for his flair for theatrical “flopping” akin to soccer players.
Giuliani’s Soccer Skills Mocked, Real ID Rules Ridiculed in Colbert’s Sharp Satire
In a segment filled with biting humor, Colbert ran through some of Rudy Giuliani’s most infamous moments, including the hair dye fiasco and his awkward scene in the film Borat Subsequent Moviefilm. Colbert cleverly tied these moments to soccer terminology, suggesting Giuliani’s skills in “dribbling” and “flopping” would make him oddly suitable for the sport. His commentary lampooned both the absurdity of the appointment and Giuliani’s public blunders.
Finally, Colbert touched on the recent Real ID policy change, which now prevents Americans without a Real ID from boarding domestic flights. While acknowledging the importance of secure identification, he highlighted the redundancy of the TSA taking a photo to verify identities—despite already having personnel check IDs visually. His observation wrapped the monologue with a sharp critique of government inefficiency, a familiar theme in Colbert’s political satire.