Jane Rosenberg, legendary courtroom sketch artist, pulls up on the Yak

Before Jane Rosenberg ever showed up on the show, The Yak crew was already talking about her work without knowing it. They pulled up a courtroom sketch of attorney Lynne Stewart next to her actual photo and decided, politely, that the sketch artist had not done her any favors.

Barstool Sports

@barstoolsports

The Yak crew thought this lawyer got a bad draw from the courtroom sketch artist and then…

That's not a bad gag to build a segment around, considering Rosenberg has actual history with this exact complaint. Back in 2015 her sketch of Tom Brady at a Deflategate hearing went viral for making him look, in her own words, less good-looking than he actually is — the internet compared it to Lurch and Gollum, and she ended up publicly apologizing to Brady and NFL fans everywhere. So when the Yak crew found another slightly rough sketch and started clowning it, the timing worked out perfectly, because Rosenberg herself was about to walk onto the show.

Rosenberg isn't some random artist, either. She's been sketching the biggest defendants in the country since 1980, when she started out drawing arraignments in New York night court. Her résumé since then reads like a true-crime index: John Gotti, Martha Stewart, Harvey Weinstein, Bill Cosby, El Chapo, Sean Combs, and, most notably, Donald Trump — a sketch that ended up on the cover of The New Yorker, the first courtroom drawing to ever land there in the magazine's history. She even turned four decades of this into a memoir, "Drawn Testimony," released last year.

The Yak

@BarstoolYak

We have court room sketch artist Jane Rosenberg joining the show!

Once she was actually in the building, or at least on the call, the crew didn't waste time pitching her on a new gig: fly her out to Chicago and let her sketch live from courtside at a game instead of a courtroom. Rosenberg's response — a coy "yeah, what if" — was enough to get the hosts convinced they'd cracked a deal.

The Yak

@BarstoolYak

"What if we flew you to Chicago and you sat on the court and drew us?" "Yeah what if." Jane Rosenberg drives a hard bargain 😂

Whether that Chicago trip actually happens is anyone's guess, but it's a fun idea on its face: the person best known for capturing Trump, Weinstein and Gotti in pastel now getting talked into drawing an NBA or NFL game for a podcast bit. Given how much mileage The Yak got out of a single guest appearance, don't be shocked if this turns into a running bit — or an actual flight to Chicago.