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May 2024

Ten Questions to a Media Lawyer

By Drew Shenkman

Drew Shenkman is Vice President and Associate General Counsel at CNN / Warner Brothers.

1. How’d you get interested in media law? What was your first job in the business?

My media law origin story begins in 6th grade, when I got my first taste of TV news in Jacksonville Mandarin Middle School’s brand-new TV studio producing its morning news show. The studio was tricked out thanks to a donation from local TV station WTLV-12, and there I was, a wide-eyed 6th grader learning how to roll prompter, work cameras, run a control room, and even master linear editing in a VHS edit bay. Around the same time, I took my first tour of CNN Center in Atlanta, where I saw it come to life before my eyes:

In high school, I joined the yearbook team, becoming Editor-in-Chief my senior year. And from the “it’s a (VERY) small world” department, I worked with Josh Pila (now of Gray TV) to co-edit our Jewish youth group’s southeast regional newsletter.

As for the law, in 8th grade, I became obsessed with CNN’s coverage of the OJ Simpson Trial, running home from the bus every day to catch the afternoon session. And soon after, I got an early legal education at Jacksonville Wolfson High School’s wood-paneled courtroom and law library.

Law and journalism came together in two pivotal moments for me. First, my summer teen-tour bus stopped in Atlanta in August 1998, where we filled the audience of CNN’s Talk Back Live. It was the same day the NY Times revealed the origin of the stain on Monica’s blue dress! (Years later, producers still remembered the panic they had finding out that they had an audience filled with 16-year-olds on that topic!).

Drew plotting his career in media law on CNN’s Talk Back Live in August, 1998.

But the second, and more important moment: during my final semester at the University of Florida, while finishing my minor from the journalism school, I took the Law of Mass Communication.  This was my “AHA!” moment. While I had already decided to go to law school, the discovery that my long-held interests in journalism and law could somehow come together into a career blew my mind. Even better, UF had a joint-degree program where I obtained my JD and earned a Masters in Arts in Mass Communications from the journalism school in a combined four years!

I eventually got an internship at the National Association of Broadcasters (with an assist from Josh Pila who was their intern the prior summer), met Chuck Tobin for lunch under his “will meet any Gator who reaches out” policy (at the encouragement of Ann Bobeck), the next summer I was Chuck’s summer associate, then I got a full-time job the next year, and the rest, they say, is history!

2. What do you like most about your job? What do you like least?

Working with everyone at CNN, especially our best-in-class legal team here in Atlanta, is hands-down the best part of my job. Everyone at CNN is brilliant, hard-working, and genuinely kind. The hardest part of the job is that sometimes we must cover tragedies that viewers can ignore. They can change the channel or decide to not read an article, but I can’t turn the news off, and some of the disturbing things we would never publish, aren’t so easily unseen or forgotten.

3. What was your highest profile or most memorable case?

My most memorable case was my first case with Chuck Tobin. We defended CNN and Nancy Grace in a high-profile wrongful death suit where the mother of a missing 4-year-old boy killed herself the day after she had been interviewed. The family claimed that the interview questions caught the woman by surprise, alleging that the interview caused her to kill herself (the mother became increasingly evasive, which irritated Nancy Grace as a former prosecutor).

However, through discovery and spending an unforgettable day at the Leesburg, Florida Police Department with Judy Mercier going through the evidence room, we discovered a CD image of the mother’s computer. After some sleuthing, we found evidence that the mother not only knew the questions she was going to be asked from her pre-interview, but she even “scripted” out answers and read them nearly word-for-word over the phone interview. The “script” became the centerpiece of our strong summary judgment motion, leading the family to voluntarily dismiss the case and even publicly apologize to CNN and Nancy Grace for suggesting they caused the suicide.

4. Do you like to be on TV, or are you more of a behind-the-camera guy?

I was on the middle school morning news show once and it was an epic disaster. I tried it again 25 years later as a guest on CNN’s Reliable Sources and it was better, I’m told. However, my proudest on-air achievement is having the birth of all three of my kids announced on CNN, what a special treasure.

The international TV debuts for Brody, Ben, and London Shenkman.

But I’m self-aware to I know I’m a better behind the camera person, especially since the secret sauce of TV news is that it takes a village. That said, I am in constant awe at how our reporters can go from on the phone with me in one moment, to the set delivering the reporting I just approved in the moment, usually without a prompter. Wish I had that talent!

5. If you had to work in one of CNN’s foreign bureaus for a year, which would you choose?

A trick question! CNN has no “foreign” bureaus because Ted Turner famously banned exclusionary terms like “foreign” in favor of more neutral, all-encompassing names like “domestic” or “international.” But to answer the question, I would choose the Rome bureau because my wife and I honeymooned in Italy, and I’d love to go back.

6. Media law can be a difficult industry to break into. What would you suggest to a young lawyer or student trying to do so?

See answer to #1, have a passion and follow it relentlessly till you strike gold. Don’t be afraid to take chances, try new things, and pivot if you hit a wall (or run through it). If someone tells you that you can’t do something, prove them wrong and show them you can (or at least try). Find alumni in the field and ask them to help (Gators always say yes!). Oh, and study hard and get good grades, none of the above helps if you don’t graduate.

7. What’s a book, show, song, movie, podcast or activity that’s been keeping you entertained this spring?

The final season of HBO’s Curb Your Enthusiasm. I watched every episode of Seinfeld in the 90s, and so I naturally love Curb. There are just so many episodes where I feel like I lived at least part of it (like, who hasn’t thought about upgrading high-holiday tickets from a scalper outside your temple, only to backtrack on the concern they might be counterfeit?).

8. I’m visiting Atlanta for a few days – what are some must-sees?

Georgia Aquarium is best in the US (sorry, Baltimore). Climbing Stone Mountain on a beautiful fall / spring day is a great time (but never during summer). Catching a Braves game is a must-do during baseball season (but make sure you have seats in the shade, or it’s the worst thing you’ll ever do). If you’re a golfer, hit me up for playing 18 holes any time. And if you’re just here passing through the airport, the Delta Sky Lounge at B gates is the best one, or F gates if flying internationally ( T and A are trying, C is meh, and just avoid D till the new one opens).

9. What are the chief things you consider when hiring outside counsel?

I primarily engage outside counsel for right of access and open records matters where, despite our own best efforts to get something we are legally entitled to, we need to go to court. I want CNN to get to the result as efficiently and quickly as possible, so I look to hire results-oriented counsel. That means expert lawyers who have tried and true practical approaches in that jurisdiction, and who want to win (without memos and long strategy calls). Extra bonus points if they can bring along other media clients also interested in joining to push for the same result.

10. CNN legal is going out for karaoke. What are you singing?

Another trick question! We would never go out to karaoke (also you don’t want to hear me sing); but we might go see CNN’s General Counsel David Vigilante play in his band. I might even request that they play a classic karaoke song, Journey’s “Don’t Stop Believin’,” which for whatever reason I can’t explain, is my favorite song (and probably, if I were to guess, David’s least favorite to play).