The Yak crew has a habit of getting a little too invested in courtroom sketches, and this week it finally paid off: they landed the actual artist. Jane Rosenberg, the sketch artist whose work has covered everyone from Tom Brady to Donald Trump over a career that stretches back to 1980, hopped on the show as a guest.
The Yak introduced Jane Rosenberg live on the show, lower-third and all, confirming she's the real deal.
It started with a bit. The hosts pulled up a Wikipedia page for attorney Lynne Stewart alongside her courtroom sketch and clowned on how far off the likeness was, the kind of riff The Yak loves running with before they realize there's a real artist willing to defend herself just a phone call away.
The crew compared Lynne Stewart's real photo to her courtroom sketch and had jokes.
Rosenberg has heard this critique before, and louder. Her most infamous sketch is the 2015 Tom Brady "Deflategate" drawing that went viral for allegedly making the quarterback look nothing like himself, a moment that's followed her career ever since and clearly set the tone for why The Yak wanted her on. She's also sketched El Chapo, Harvey Weinstein, Ghislaine Maxwell and, most recently, Trump's arraignment, a sketch The New Yorker put on its cover, so she's not exactly a rookie taking heat for the first time.
Naturally, the hosts tried to get her courtside for something a little less legal. When they floated flying her out to Chicago to sketch a game instead of a defendant, she didn't exactly say yes, but she didn't say no either.
The hosts pitched flying Rosenberg to Chicago to sketch courtside, and she gave a coy non-answer.
It's a strange but very Barstool crossover: a woman with a 2024 memoir titled "Drawn Testimony" and four decades of drawing mob bosses and disgraced billionaires, trading jokes with a podcast crew about a lawyer's chin. Whether the Chicago courtside pitch ever actually happens is another question, but for one episode, The Yak got the artist behind some of the most talked-about faces in courtroom history to sit there and take the ribbing herself.