Interview with Courtroom Artist Behind Madoff, Cosby, Weinstein Sketches

Bernie Madoff courtroom sketch Jane Rosenberg

Bernie Madoff, by Jane Rosenberg

If you’re paying attention you’ve probably seen her work. For more than 40 years, Jane Rosenberg has been a courtroom artist, sketching figures including Bernie Madoff, El Chapo, “Pharma Bro” Martin Shkreli, Bill Cosby, Martha Stewart, John Gotti, Harvey Weinstein, Tom Brady, Ghislaine Maxwell, and most recently, Frank James, the Brooklyn subway shooter. (We found out about that last one after conducting the interview below).


When cameras aren’t permitted, Rosenberg is there as the people’s eye, using a collection of pastels she picks up near her Upper West Side apartment.

ILTUWS recently caught up with Jane at her favorite Upper West Side hangout, Samad’s Gourmet at 2867 Broadway, between 111th and 112th streets. We got to chatting about the trajectory of her artistic career, what she loves about the Upper West Side, her family, and advice she’d like to share with future generations of artists.

Jane Rosenberg interview

The following interview has been edited for length and clarity.

Bobby Panza: Jane, you describe Samad’s as your West Side Story. What’s the story there?

Jane Rosenberg: I basically come here just about every single day if I’m not working in a courtroom. I come out of my apartment and I come here, sit on the bench, have some coffee, watch people go by. It’s my escape. I can regroup myself; reset, ready for the day. And get some air. I don’t want to have cabin fever.

What’s your go-to order at Samad’s?

It’s so exciting because I’m so warm today that I could have ice decaf coffee. I always have decaf. I don’t drink caffeine anymore because it was long ago very addictive and gave me headaches.

But I love it in the summer, I have iced coffee. I love drinking it from a straw. But now it’s the first time in the season I’m having an ice coffee because it’s warm today, which is exciting. I’m very happy to be here. It’s very relaxing. No, not a worry in the world but I’m sitting here.

What do you love most about being here on the Upper West Side?

For one thing, if I’m coming out; this is a local neighborhood. I know the owners, they see me every day. I’m a regular customer, they know what I like. They take care of me. They watch over me. I feel safe here. I have an awning over my head in case it rains. I’ll come here rain or shine or snow or whatever. I’m out here in all weather.

I have the clothing for all weather because I did a lot of plein air painting throughout the winter, so I have all the right gear to wear. And I don’t care, I just need to be out here. It’s exciting. And I want to support my local store. It’s my community, small business, I support it.


What are your favorite tools to work with in the courtroom?

I have my gear all set up by my front door, ready to go because I’m on call for work; I can get called any day at any time. Sometimes I know in advance and that’s always a wonderful thing. But there are times when, in the middle of the day, somebody big is arrested — and I’ll have to run out to an arraignment.

So, my kit is all by the door. I bring a portfolio with my paper and a heavy bag with a box I made 40 years ago that has a million little stubs of pastels. During the pandemic I ordered even more pastels so I have extra boxes that I throw in there.

I have a tripod in case I get seated in the jury box. I have to rest my box on something. So, I have a little tripod I put it on. If I’m on a bench, I can just put the box on the bench next to me. I have my binoculars so I can see very far away to draw people’s portraits … and paper towels because I’m a mess. And a luggage cart that I carry it all on.

Nowadays I have even more because I have all those extra pastels. I had to buy a little stool; so I have the tripod on one side and I have a stool on the other. It’s like a folding little children’s kiddie bench that I bought in the neighborhood at a hardware store.

There’s a lot of stuff. It’s too heavy. It’s ridiculous. I’m getting older and carrying too much gear. And I think there’s more but I forget without looking at it.

Martha Stewart courtroom sketch

Martha Stewart, by Jane Rosenberg

Do you have your own reserved space in the courtroom? Should people know you’re coming and get out of the way?

Oh no, I wish I had my own space [laughing]. When I’m going into a court building I have to go through the metal detectors. And I have to go and get on line. I am known in certain buildings and I sometimes there are a few artists seats reserved for me if I let them know in advance.

If they have artists seats, I still want the best view I can get because certain angles are better than others. I’m not the only artist in the city so I have to worry about that. I always go to court very early in the day, as early as I can, if I know in advance. Otherwise I’m just running down there.


Do you have a favorite spot to set up in the courtroom?

That depends on what I’m doing and what courtroom. It varies and I don’t always get my favorite spot. During the Ghislaine Maxwell trial I was seated in the third or fourth row.

ghislaine maxwell courtroom sketch

Ghislaine Maxwell, by Jane Rosenberg

Sarah Palin trial vs. New York Times. I was in the front row there. They gave me a really good seat in the jury box. It always varies. There’s not one spot. My favorite spot is wherever I can see and wherever they’ll let me sit that I can see. It doesn’t always work out for me.

Going back to Ghislaine Maxwell. You’re out there doing your job and Ghislaine starts sketching you back. There was another time when Eddie Murphy sketched you back. I bet that was a pretty funny moment, him being a comedian. Did you remember that moment?

Yes, I certainly do. I have the sketch somewhere in my apartment. He was mocking me. He was bobbing his head up and down, looking at me, turning around, swiveling up-down-up-down. And he was making fun. People were laughing and they were noticing. He gave it to me. It was on a little tiny post it. Yeah, ridiculous little sketch of me, but, yeah, I got it.

Ghislaine, I did not get the sketch and I never saw it. I did ask her lawyer. But she said, “You know Jane, I can’t tell you.” So, I never did see what she sketched.

Ghislaine Maxwell sketches Jane Rosenberg

Ghislaine Maxwell sketching Jane Rosenberg, by Jane Rosenberg

She has twin sisters and they both sketched in court. They both brought little tiny sketch pads. I looked over the shoulder at one of them and I could see she was doing a tiny sketch of Ghislaine’s lawyer. It wasn’t too bad. Pencil drawing, tiny.

You’re still anticipating crossing paths with Ghislaine Maxwell again, right? You’ll be there at the sentencing in June?

Yes, I will.


What I find interesting about your work, and I see it over and over, is that you’re there in the moment and you capture an energy. That’s how I interpret your work.

And that’s what I do. Exactly. Thank you. Yes, that’s my goal, and that is what I do.

I think that there was a moment in time where people who didn’t really understand your craft kind of bubbled up to the surface. Going back to the Tom Brady moment, when you sketched him in the Deflategate hearing, I thought you did a great job being in the moment, capturing the energy. For all his Super Bowls and successes, he was still in a Judiciary hearing for alleged cheating and that couldn’t have been fun for him. That’s what I saw. You got it.

Then I was reading that some people didn’t like how Tom Brady’s sketch came out, and their outrage went viral. Someone wrote they thought that you were a Jets fan [laughing]. Do you like football?

I Know nothing about football, zero. Yeah. I didn’t know who Tom Brady was either.

You painted a new portrait of Brady. What motived you to do the second one?

Nothing motivates me, except if I was assigned. I wouldn’t want to draw him just for the fun of it. Somebody must have asked me to do it.

My brother’s a big time Patriots fan. I wonder if we told the same Patriots fans who said they didn’t like the first Brady portrait that they could have it to hang on their wall now, would they take it? It’s imbued with this great story [laughing]. The original! I bet they would.

I have been offered quite a bit of money for it.

I heard you’re selling it for a million dollars, right?


One million bucks. Boom. See ya, Brady.



We can talk about the courtroom work all day, I bet. But you’re also a beautiful artist outside of the courtroom too. What type of work do you enjoy on your own?

I like doing oil paintings of cityscapes. I am not doing plein air painting on the streets of the city right now. I don’t want to bring my easel out here and focus on a canvas because it doesn’t feel really safe here on the streets of the city. Since the pandemic there’s a lot of random crime, there’s a lot of homelessness and emotionally disturbed people. It doesn’t feel comfortable for me, to not be paying attention to what’s going on around me.

West 73rd Street Verdi Square, melting snow dusk, 15 x 20, oil on board, by Jane Rosenberg

I do go out all the time but I don’t want to disappear into a canvas. I still like painting cityscapes. I’m a New Yorker, I love New York City. This is where I live. And this is what I paint; scenes with people in them. I don’t do just empty streets. There’s always got to be people doing, living New York life.

Jane Rosenberg Lou Freeman

Jane and husband Lou Freeman

Do you and your husband get to spend some time away from this bench?

[laughing] Not lately. Lou and I both work a lot and we haven’t been on a vacation in a couple of years because of the pandemic. Right after the Harvey Weinstein trial I had planned to go away, but it was about the height of the pandemic beginning.

Harvey Weinstein courtroom sketch

Harvey Weinstein, by Jane Rosenberg

And then again, I was on the Ghislaine Maxwell trial and we both set a time frame where we both were free to take vacation, but that trial ended and it was the height of Omicron. So, we didn’t go anywhere; I’m desperate for vacation.

Where would you like to go?

Just anywhere. I’d like to just lay on a beach, honestly. In a warm climate at the moment. That’s how I feel. But I’d be happy to just go anywhere. Anytime I get out of the city, even if it’s just to Long Island for a minute to visit my sister and brother … I’m just excited to get out of the city. I love the city but I do need breaks.


Did you grow up in the city?

I grew up in Long Island and I live in the city now.

Do you know when you had your breakthrough? When you first knew you wanted to be an artist?

My breakthrough? I was always an artist. My mother said I spent hours peeling crayons in the crib. I always enjoyed art. I took little side electives in high school and I was an art major in college (SUNY Buffalo). Then I went to the Art Students League for many, many years after college and I studied art. Always, I still study art. I’m still always feeling like I’m an art student and always trying to grow and get better.

Rowboats in Central Park, 11 x 14, oil on board, by Jane Rosenberg

Rowboats in Central Park, 11 x 14, oil on board, by Jane Rosenberg

I had a breakthrough moment with courtroom art, though. I decided I have to make money. I was struggling as an artist for many, many years. After college I didn’t know what I was going to do but I always loved art. I had to be an artist. There was nothing else I wanted to do or could do, but I didn’t know how to make money at it. That’s a different question. How did I learn to make money at it…

Yeah, let’s go down that road.

I did everything. I used to draw on chalk drawings right on the sidewalk. On my hands and knees. I copied Rembrandt and Vermeer’s. I had a hat out. I was trying to make a living.

I did portraits in Cape Cod for tourists. I would do that in the summer and I’d go to the Art Students League in the winter. I was a struggling artist for many years. And then I went to a lecture by another courtroom artist at the Society of Illustrators. And I thought, wow, I wish I could do this. I don’t know if I’m good enough. That’s when I took a look in the mirror and said I’m going to do this. I’m going after it.

I had lawyer friends who took me to night court at 100 Centre. I sketched prostitutes back then … this is 1980. I asked the court officers where the artists sit. They said to come next week and they’d let me sit in the jury box with the other artists. I had so many questions, like, what did artists bring?

So, I went and there were two other artists, one had Fox on his portfolio and the other had nothing. Then I made my first call. I called CNN and they were just a startup company.

And they said, “Well, we had another artist there,” and I thought, oh no. Now I have to call one of the big three. So, I called NBC and they said “Come on in. Let’s see what you got.”

I went in and showed them my sketch and they said “great.” They showed me around the newsroom and they put my sketch up on a wall and shot it. Then they took me in the back room to the finance person and I went home and I called my parents and I said, “I’m on TV!”

I was very excited. I watched it on a tiny little black and white TV in my living room and that was the beginning, and I was really excited. And I kept getting called and that’s what I’ve been doing ever since 1980.

That’s interesting. You met your husband in the courtroom?

Yes. I met him in Brooklyn Federal Court.


When we hung out here last time, Lou told me about the time you sketched him on the phone.

I sketched him on the phone because he was always on the phone. He still is always on the phone. In those days it was a handheld phone.

It was an oil painting. It wasn’t even a sketch but he never would pose for me. That’s the only time I got him to sit still. So, it was great. Yeah, that’s what I have with him. That’s what lawyers do, they’re always on the phone.

New Yorkers’ 7 PM Cheer to Essential Workers during Pandemic, 18 x 14, oil on board, by Jane Rosenberg

Do you have advice or anything you would say to aspiring artists today?

I get a lot of emails from aspiring courtroom artists. I would advise them to go into a courtroom. Courtrooms are open to the public. Give it a try. Go ahead and see if you really like it.

It’s very hard. There are a lot of complications with being a courtroom artist. You have to worry about what you can see; there’s a lot more equipment nowadays. There’s big computer monitors everywhere blocking you. There’s giant furniture, podiums. It’s not like what it used to be in the early days; when there were no computer monitors because now they make walls of blockage for me, it’s really hard. But courtrooms are open and you can try it out if you want to be a courtroom artist.

For an aspiring artist … just go ahead and do it. It’s fun. It’s exciting. It’s a journey, enjoy it. You have to do what you have to do. Study it … and do it.

When I went to college, abstract art was big. I was a closet portrait artist. It had been discouraged when I was in college, it was passé. I was supposed to find the next new thing to do.

Have you made any friends doing courtroom sketches? [laughing] Have you ever sketched somebody in court and go out for a beer or something with them afterwards?

No! No way! [laughing]. They’re usually in jail afterwards.

[laughing] On that note. How did it feel seeing Ghislaine Maxwell sketching you back?

I was just busy working. I didn’t react. I didn’t even know it was a big deal. Actually, it was two weeks after I did the sketch that it went viral. I didn’t even know; people were calling me for an interview. I said, “what’s going on?”

I don’t do social media. So, I didn’t really know. It wasn’t unusual but it wasn’t a big deal. I just kept sketching her. I’m not going to let it bother me.


Yeah, you’ve done this a bunch of times before.

I’m a professional. I have to do my job. I’m not going to stop drawing because somebody is drawing me. It was just, “Okay, one more thing is happening, now I have to draw that. She’s drawing me, that’s what’s happening. I’m going to draw her.”

You’ve certainly been in a lot of pressure cooker courtroom proceedings with a lot of people. Do people ever seek you out after a case to discuss your work? You know, opinions about it? Do subjects you’ve sketched ever want to reconnect to do another one or just be critics about it?

That’s what happens on social media, which is what I don’t do. I mean, I get positive and negative feedback. I get emails sometimes. Usually if somebody is going to seek me out or email me they’re going to say something positive about my work, which is nice. I appreciate that.

The negative things are more social media. I do get email requests to purchase art that I’ve done. And some commission requests.

by Jane Rosenberg

Would you say that there were certain pieces throughout your life or certain cases throughout your life that have gotten you more attention?

That’s all been since social media. That’s where I get more attention than I want. That started happening since Tom Brady; I get more attention than I want on social media in a lot of cases. It’s a positive and negative. I got positive attention on Harvey Weinstein. I got it on Ghislaine Maxwell and Martin Shkreli (Pharma Bro). Oh, Steve Bannon. I did a sketch that got a lot of positive attention of Steve Bannon.


How long have you been living on the Upper West Side?

30 something years.

Did Lou live on Upper West Side when you met him?

Yes, he did. I moved into his neighborhood.

Was that an easy assimilation for you?

No, marriage and having children and my career; it was always a big adjustment. I had been single a long time. It was a lot to deal with. I’m very happy. I’m very happy with Lou. I think I waited long enough and I picked a great husband. We got married in 1989.

Where were you living prior to coming to the Upper West Side?

I had a rent stabilized apartment on the Upper East Side, which wasn’t the greatest neighborhood. I moved there in 1974 or something. It was on Second Avenue and 89th Street. Back then it wasn’t so gentrified. They were just building Ruppert Towers back then. It was a very weird neighborhood when I first moved there.

It got very gentrified now and they built that Second Avenue subway which could have been really nice. I was so far away from the subway where I lived back then. Now, the subway is really close. Very different.

How many kids do you have?

I have a kid. A grown son.

Did you like raising a kid in the city?

It’s the only place I’ve ever raised a kid, in the city. And I do like it. I think it’s great. I love the city and I love how my son has so many friends. It was so easy.

The city has great schools. It has potential for a great social life. He was very into sports and he still is.

It was a lot. It was great. I love the city. I love all the people. I’m a people person. Not really, I want to be alone but I love being around people. [both laughing]. I don’t want to be living in the woods all by myself.

What are some of your favorite places to shop on the Upper West Side?

Zabar’s, Citarella. I shop at West Side Market, right here, almost every day. That’s what’s near me. In general, that’s where I shop. If I need something other than that I’ll go to another neighborhood on the Upper West Side.

I still have the same favorite things I like to eat and I like my husband to cook. I like it when he makes me fresh fish. We go to the neighborhood farmers market, buy ingredients and he cooks them. That’s always great.


Shifting gears. The art tools that you use. Do you have certain stuff like brushes or pastels that are your preferred ‘go-to’ gear?

You know what else is great? Janoff’s Art Supply store is right across the street. Local. And I love that it’s there. I support them as much as I can. They don’t have everything I need so I do still have to order my art supplies online but they do have some pastels. They’re expensive but I don’t care because they’re a local business. I’ll buy my pastels there if I can and whatever I can’t buy there I have to order online. It’s just a real gift to me that I have an art supply store across the street from me. Even though it’s small.

If somebody were to assemble a Jane Rosenberg art supply starter kit, what would be in there?

You can just take a pencil and paper and sketch people on the subway, in the moment. Starter Kit? No such thing. If you want to be a court artist, take a pencil and paper and learn how to draw. That’s the first thing. Nowadays people don’t even use pencil and paper, it’s tablets. People draw on those electronic devices.

That’s why I like your work. It feels real.

It’s a different world now.

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