As the trial of Sean “Diddy” Combs continues to play out in court, Diddy has revealed his shady side through his behind-the-scenes antics. From Diddy’s failed attempt to seek a mistrial to making eyes at the jury, Diddy has found himself in hot water with the judge. Now, it seems that Diddy’s ego has once again ballooned past his immediate circumstances, as the “All About The Benjamins” rapper has picked a fight with courtroom sketch artist Jane Rosenberg.
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Since Diddy’s trial will not be televised, much of the imagery coming from the court is provided by Rosenberg — a well-established artist with decades of experience. According to Reuters, Diddy asked Rosenberg to “Soften me up a bit, you’re making me look like a koala bear.” While it’s not the first time Rosenberg has had a high profile defendant request she alter their appearance for the public, it does beg the question of if Diddy knows what a koala actually looks like.
However, Diddy does have some powerful allies who’ve been disgruntled over Rosenberg’s work in the past — and this just might help increase his chances of getting a pardon from President Donald Trump.
Diddy and Donald Trump have a courtroom sketch artist in common
The career of Jane Rosenberg has included many buzzed-about trials, several of which include members of President Donald Trump’s inner circle. According to Reuters, Rudy Giuliani disagreed with the way Rosenberg drew his likeness, Donald Trump Jr. asked her to “Make me look sexy,” and the president himself was sketched by Rosenberg during Donald’s hush money trial in 2024. Which might just be what Sean “Diddy” Combs needs to win Donald over and potentially pardon him, should he ultimately be found guilty.
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The president said in May 2025 that even though no one has asked him yet, he’d be interested in taking a “look at the facts,” of the case (via the Daily Beast). This caused rapper 50 Cent, one of the celebrities who has spoken out against Diddy, to unleash a series of since-deleted Instagram posts pointing out all the reasons why Donald should not pardon Diddy. According to USA Today, 50 Cent — whose real name is Curtis James Jackson III — alleged that Diddy has “said some really bad things about Trump.” This tactic to prevent Diddy from receiving a future pardon might work well for 50 Cent, who noted that “Donald doesn’t take well to disrespect,” while also indicating he has more proof of Diddy bad mouthing the president.
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For now, it’s clear that Diddy simply can’t read the room, and is pulling out all the stops to keep attention on himself — for better or for worse.
