Skip to main content
June 2022

Ten Questions to a Media Lawyer: Randy Shapiro

By Randy Shapiro

Randy Shapiro, the MLRC’s current board chair, has been Global Newsroom Counsel at Bloomberg for the last nine years. Before that, Randy was the General Counsel of The Newsweek/Daily Beast Company.

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

My first year law school courses didn’t really grab me (in fact, I’d say Property Law propelled me in the opposite direction). Second year, I had a fantastic Con Law teacher and I was hooked — even more so when I took her Political and Civil Liberties class. My first stint as a media lawyer was right out of law school, when I joined Stroock’s litigation department and became the junior person on the New York Post team. I worked on a number of lawsuits for the Post and even got to vet gossip columnist Cindy Adams on occasion — always a treat.

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

What I like the most: every day is different. I wake up with a daily to-do list. Most days, something (often exciting) happens and derails me, but I’m always learning and forced to think on my feet. The varied nature of the work is truly amazing, both in terms of topic and jurisdiction: Turkey, Russia, France, Germany and, of course, the UK, where we recently were before the Supreme Court and ended up with an unfortunate decision on privacy law. At least it’s always interesting.

What I like the least: I am now wired to open at least one eye around 5am and look at emails, as I can’t stop myself from thinking about what may have happened over my night in other jurisdictions. I’d like a little more sleep.

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

I spent a lot of quality time with Mike Isikoff both before and after Newsweek was sued for one of Mike’s many stories during the Clinton administration (no — not that one …). The plaintiff had been a source who, through her own admission during a prepublication fact-check, had lied to Mike during their first encounter. Newsweek’s article detailed that chronology. The source essentially sued for breach of contract, claiming Mike had promised her confidentiality. We argued, successfully, that false information could not constitute consideration and therefore no enforceable contract existed. Mike and I are still good friends and, to this day, he asks me how much Newsweek spent on Cravath to defend his honor. I’ll never tell.

4. Advice for firm lawyers trying to pick up media clients?

First, join the MLRC! No — seriously. Second, understand what your potential client needs. Ask your in-house contact what the issues are that keep them up at night. Third, don’t send long memos. Actually, don’t send any memos. Media lawyers tend to move at a brisk pace, especially if they are sitting in a newsroom. Unless we’re working on a litigation together, with very rare exception, I’m not hiring you to produce a think piece with every conceivable outcome. I want your best judgment on how to handle an urgent situation.

5. Biggest mistake a lawyer can make?

This one is easy: be self-aware (and modest) enough to know when you don’t know the answer to a question. Don’t fake it. But then figure out how to get that answer, whether it’s from doing your own research, tapping into colleagues who have experience on the issue, or looking to outside counsel (if you’re in-house). I like to say in my newsroom trainings that I know enough to be dangerous in a lot of jurisdictions. I also know enough to know when I need help.

6. What’s a favorite book or movie involving the law?

Hard to choose. But while I love “To Kill a Mockingbird,” “A Few Good Men” and “The Verdict,” for sheer entertainment value, I’ve gotta go with “Legally Blonde.” You’ll hear “I’m taking the dog!” uttered frequently in my household.

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

Network, network, network. The good news is: networking includes forming friendships with people whom you should genuinely find interesting. As a junior associate, I would attend PLI’s annual Communications Law conference, where I would try to come up with a passably intelligent question to ask the presenters who seemed the most approachable. Through that process, I made good connections, and one of them ultimately led me to my first in-house job. Also, you make your own luck. Finding the jobs that you really want isn’t a matter of happenstance. You forge the connections, you keep in touch and, eventually, you’re in the right place at the right time.

8. What’s a book, show, song, movie, podcast or activity that’s been keeping you entertained during the pandemic?

My husband and I have watched a lot more TV than we previously did. We probably are the last people we know who watched “The Crown” and “Downton Abbey.” We’re now trying to cram in five seasons of “Poldark” before an upcoming trip to Cornwall. After he goes to sleep, that’s when I watch the really good stuff. I highly recommend “Dark,” “Glitch” and “All of Us are Dead” (I love Korean zombie shows — it’s a thing).

9. What’s a typical weekday lunch?

If it’s a good day, a salad from the plethora of salad-to-go places surrounding my office. More often than not, though, it’s a melange of snacks from the bountiful Bloomberg pantry: my recyclable plate could include an artful arrangement of pepper-flavored turkey jerky, a package of chili and oregano olives, cheddar chickpea puffs. The possibilities really are endless.

Mimi dressed up for Halloween

10. Your most important client takes you out for karaoke. What do you sing?

I might revert to “A Bushel and a Peck” (from “Guys and Dolls”), which I sing every morning to my dog, Mimi, as we go downstairs for her first walk of the day (apologies to our neighbors who’ve had the misfortune of getting on the elevator with us). I also do a mean Bee Gees impression — so “Stayin’ Alive” or “Night Fever” are on the table, as is Natalie Merchant (our ranges match). But I think I finally may have moved on from the musical stylings of my first crush, Barry Manilow. Actually, who am I kidding? I’m still a Fanilow.