Diddy brought a moment of fun to a tense courtroom Thursday when he turned to veteran sketch artist Jane Rosenberg with a playful complaint: “Soften me up a bit, you’re making me look like a koala bear.”
The 55-year-old is on trial in Manhattan federal court, facing five serious criminal charges, including racketeering conspiracy and sex trafficking. He has pleaded not guilty. With cameras banned from the courtroom, Rosenberg has been tasked with illustrating the high-profile proceedings for Reuters.
Known for his evolving style, once Puff Daddy, then P. Diddy, and now Diddy, the mogul has been attending court daily in modest attire, typically sweaters, while sporting a graying goatee and hair.
Though Diddy’s comment stood out, Rosenberg is no stranger to courtroom critiques from famous figures. Earlier this year, Rudy Giuliani told her she made him “look like his dog.” And during a civil fraud case in 2023, Donald Trump Jr. gave her this note: “Make me look sexy.”
Still, Diddy’s behavior wasn’t all light-hearted. Judge Arun Subramanian issued a stern warning after noticing he was nodding toward the jury during his attorney’s cross-examination. The judge said the interaction was “unacceptable” and warned that Diddy would be removed from the courtroom if it happened again.
If convicted, the music tycoon could face life in prison. Yet despite the gravity of the situation, Diddy has managed to maintain occasional moments of humor, even during one of the most serious battles of his life.
The Diddy sketch artist needs to be put on trial next pic.twitter.com/sXixouXUnG
— Jayroo (@jayroo69) May 14, 2025
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