Meet the Sketch Artist Who Drew Diddy — and Learn the Peculiar Thing He Told Her (Exclusive)

For weeks, crowds flocked to a federal courthouse in Manhattan for Sean “Diddy” Combs’ high-profile sex crimes trial. But Jane Rosenberg had a different reason for being there: She was one of three courtroom sketch artists capturing the proceedings.

With her sketch pad and pencils, Rosenberg, who lives in New York City, went where cameras were legally not allowed — and her sketches were among the only public glimpses of Combs, who this week was acquitted of sex trafficking and racketeering conspiracy charges. He was convicted of lesser charges of transportation to engage in prostitution, and will be sentenced at a later date.

Over the last 45 years, Rosenberg said she has drawn sketches for every high-profile trial in New York — and sometimes beyond. She’s drawn sketches of John Gotti, Martha Stewart President Donald Trump, Bill Cosby, Harvey Weinstein, Rudy Giuliani and even Derek Chauvin.

Chauvin’s trial posed unique challenges, Rosenberg said, because it took place during the COVID-19 pandemic and there was limited seating in the courtroom. Rosenberg said she drew sketches from a Reuters live feed. She also was a sketch artist at Combs’ 2001 trial, in which he was acquitted of all charges related to a nightclub shooting that injured three people.

After that trial, one of Combs’ attorneys, Johnnie Cochran, contacted her about buying some of her trial sketches, Rosenberg said. But the day he proposed they meet for him to review them was the same evening of her son’s science fair. And they ultimately never met up.

Throughout her career, Rosenberg said some high-profile figures have critiqued her depictions of them — most recently, Combs.

“Giuliani told me I made him look like his dog, Weinstein told me to give him more hair, John Gotti asked me to trim down his chin,” Rosenberg told PEOPLE in an interview Tuesday, a day before a jury of eight men and four women returned a mixed verdict in Combs’ case.

“And Trump once stood over one of my sketches and said, ‘I need to lose some weight,'” she said.

Last month, during a break in proceedings in Combs’ trial, Rosenberg said, Combs returned to the courtroom and mouthed something to her that she couldn’t quite make out. But he repeated himself and she heard him loud and clear.

He told her to make him look “softer,” and motioned to his mouth. “And he said, ‘You made me look like a koala bear,'” she recalled.

Later that same day, Rosenberg said she rode on an elevator with Combs’ mother Janice Combs, who was a frequent presence at the trial, along with Combs’ sons. “In the elevator, they were saying, ‘Thank you for being such an unbiased artist,'” Rosenberg said. “And I told them, ‘Today, Diddy said I made him look like a koala bear.’ And they all started chuckling.”

Rosenberg is no stranger to criticism. In 2015, during a hearing on “Deflategate” — the NFL scandal in which Tom Brady was accused of using underinflated footballs to gain a competitive edge — her sketch of Brady prompted backlash and even death threats. Rosenberg said she doesn’t use social media and didn’t even know who Brady was when she drew him.

Related Stories

Sean ‘Diddy’ Combs Denied Bail: Here’s Why Judge Kept Him Behind Bars

Sean ‘Diddy’ Combs Acquitted of Most Serious Counts, Convicted on Prostitution Charges

“People found me and hunted me down,” she said.

One night, when she returned home from work, she said she had received hundreds of emails. Fans of Brady criticized her, while those who disliked him celebrated how she had depicted him.

“I didn’t know what memes were,” she said. “But I certainly learned then what memes were.”

Rosenberg said she enjoyed drawing Trump “because he’s got the bushy eyebrows and the hair and he always had that pouty face.”

Drawing celebrities is a challenging task, Rosenberg said, because they are widely known and people have a perception of how they are supposed to look.

Rosenberg said it took her some time to understand how to draw Combs.

“He was not a simple likeness to do,” she said, adding that she had to learn to draw his jaw.

“He’s got an unusual look,” she said. “And he doesn’t look anything like he used to.”