In this episode of GC Sidebar, Paragon Legal CEO Trista Engel sits down with Eric Greenberg, General Counsel at Cox Media Group, for a candid conversation on legal strategy, cross-functional leadership, and knowing when not to play by someone else’s rules.
Eric shares thoughtful insight into how GCs can map strategy end to end, why context is a form of leverage, and how legal leaders can shape better outcomes by helping redefine the game itself.
From tough negotiations to leading through complexity, Eric offers sharp, grounded advice for today’s evolving in-house counsel, plus his pick for favorite fictional lawyer. Watch now.
Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Eric Greenberg, EVP, General Counsel & Corporate Secretary at Cox Media Group
Trista Engel:
Hi, I’m Trista Engel, CEO of Paragon Legal, and welcome to GC Sidebar, a short and sharp conversation series with today’s most forward-thinking general counsel.
In just four questions, we cover the legal industry, leadership, careers, and a little fun.
Today I’m joined by Eric Greenberg, Executive Vice President, General Counsel, and Corporate Secretary at Cox Media Group, a PE-backed multi-platform media company serving over 60 million Americans in 10 major U.S. markets.
Eric began his legal career at Covington & Burling and then moved to the Office of Legal Counsel at the Department of Justice. He returned to private practice, holding partner-level roles at Covington, Paul Hastings, and Perkins Coie.
He stepped into his first general counsel role at Cox Media Group in 2021.
Beyond his legal expertise, Eric is a strong advocate for the strategic integration of legal ops within corporate legal departments. I can personally vouch for his thoughtful commentary on the subject, including a fantastic webinar he led with Paragon and his head of legal ops last year.
Eric, welcome, and thank you so much for being here.
Eric Greenberg:
Thanks for having me. I’m excited to be here.
Trista Engel:
Let’s jump in.
What is the biggest challenge facing GCs and in-house legal teams today?
Eric Greenberg:
I think the biggest challenge, and also the biggest opportunity, is the increasingly strategic nature of the GC role.
We’re moving away from a model where someone calls legal only when there’s a legal issue, and toward one where the GC is at the table, helping map company strategy. That shift comes with tremendous opportunity for GCs to leverage their unique skillset, spotting issues, remaining neutral across functions, and orchestrating across disciplines.
It’s a big change, but also the most exciting part of the job.
Trista Engel:
That really is making legal a core part of the business, not just an advisor to it.
What accomplishment are you most proud of in your current role?
Eric Greenberg:
It’s integrating a cross-disciplinary strategy that helped us negotiate significantly better terms in some major contracts.
We used legal as a kind of R&D lab, researching legal claims, policy issues, public affairs strategies, and deployed that in a composite approach. We weren’t just playing the game the bigger party created, we changed the game entirely.
And the results were tangible, real numbers, real outcomes. It’s one of those rare moments where legal can clearly say, “That success? That was us.”
Trista Engel:
I love that. That’s not only intellectually exciting, but a real example of breaking the status quo and redefining impact.
What’s one career moment that changed your trajectory?
Eric Greenberg:
Early in my career, I made a lateral move from litigation to corporate work. I had the presence of a seasoned lawyer but zero corporate experience.
A partner asked me to mark up a ship mortgage and said, “Just look up the forms in the library and copy anything that’s missing.” I did exactly that, pencil in hand.
Later, in a negotiation, a junior partner on the other side questioned one of my edits. I had no idea what the language meant, so I said, “All I can tell you is that language has appeared in every ship mortgage I’ve ever seen.”
He paused. Looked at it. Then agreed.
That moment transformed me from a middling litigator into a rising star transactional associate. It was the inflection point of my career.
Trista Engel:
That’s a fabulous story. And you’re a great storyteller, by the way.
Eric Greenberg:
Thanks! For the record, I still don’t know anything about ship mortgages. But that experience taught me the power of silence, something I’ve carried into every negotiation since.
Trista Engel:
If you weren’t an attorney, what would you be?
Eric Greenberg:
Since fifth grade, my dream has been to host the Today Show.
I’ve always loved news, politics, movies, theater, the idea of a talk show that mixes all that is really appealing. At one point, I told someone my goal was to host Weekend Today, and my wife called me out, “What happened to aiming for Today?” I told her I was trying to be realistic!
Trista Engel:
Well, I could definitely see you doing that. When Hoda retires, we’ll keep an eye on that spot for you.
Eric Greenberg:
If they ever need a fractional host, I’m available.
Trista Engel:
All right, bonus question, who is your favorite fictional lawyer?
Eric Greenberg:
Henry Drummond, from Inherit the Wind. He’s based on Clarence Darrow and played by Spencer Tracy in the movie.
That story, and that character, have stuck with me ever since high school drama class, when my teacher told me, “If we ever do Inherit the Wind, you can play Drummond and pace all you want.”
I looked into the play, and it’s one of my favorites to this day.
Trista Engel:
That’s a great pick. Eric, this has been so much fun. Thank you for your stories, your insights, and for joining us today.
Eric Greenberg:
Thank you for having me.
Trista Engel:
All right, that’s a wrap on today’s episode of GC Sidebar. Catch more great conversations on our website at paragonlegal.com. Thanks for tuning in.
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