Gary Ginsberg

Author, Political Campaigner, and Corporate Advisor

I was hoping to do with [First Friends] what George did with politics: to popularize it, make it accessible and an easy entry point for understanding American history.

Summary

This week on "Leadership Matters," Alan is joined by another longtime advisor to executives, Gary Ginsberg, for a discussion about Gary’s career, recent book, and observations on leadership across nearly four decades of work in the public and private sectors.

Gary first made a name for himself in Democratic politics, working on presidential campaigns across the 1980s. He has worn many hats over the course of his career, serving as a senior vetter in the Clinton Administration, a top role at JFK Jr.’s George Magazine, and as a communications specialist for corporate giants like News Corporation, Time Warner, and SoftBank. Recently, Gary has become an author, writing in First Friends about the roles that close personal friends of American president have played in shaping the country that we know today.

Gary and Alan’s conversation covers a broad range of topics, from their recollections of Democratic politics before the Clinton era to observations about trust and leadership in executive positions. Gary offers insightful perspectives on the variety of leadership styles he has personally observed and warns corporate leaders that even staid businesses are prone to disruption — executives should never rest easy, as today’s cash cow can quickly become tomorrow’s left-behind incumbent.

Mentions & Resources in this Episode

• Gary Hart

• “Remembering the essence of John F. Kennedy Jr.,” by Gary Ginsberg

• Gary Ginsberg on George magazine, 1998

• First Friends: The Powerful, Unsung (And Unelected) People Who Shaped Our Presidents, By Gary Ginsberg

Guest Bio

Gary L. Ginsberg is a lawyer, American political consultant and corporate adviser, serving as a strategist in both the public and private sectors for more than 25 years. 

Until 2020, he was Senior Vice President and Global Head of Communications at SoftBank Group Corp.

Before joining SoftBank, Ginsberg served as Executive Vice President of Corporate Marketing and Communications at Time Warner Inc. In this role, Mr. Ginsberg worked with the Company's senior management team and top executives at its operating divisions on a wide range of corporate matters, with direct responsibility for the Time Warner's marketing and communications initiatives.

Before joining Time Warner, Mr. Ginsberg was the Executive Vice President of Global Marketing and Corporate Affairs at News Corporation. Mr. Ginsberg coordinated and executed the Company's global marketing and investor relations programs, as well as its corporate affairs, strategic communications and philanthropic efforts. Mr. Ginsberg originally joined News Corporation in 1999 as Executive Vice President of Corporate Communications. He was appointed to the Company's Executive Management Committee in 2000 and to the seven-member Office of the Chairman in 2007.

Prior to News Corp., Mr. Ginsberg was a managing director at the New York-based strategic consulting firm of Clark & Weinstock. Previously, he was a senior editor and counsel at George, the monthly political magazine, and a former Assistant Counsel to President Clinton.

Mr. Ginsberg began his professional career as an attorney with Simpson Thacher & Bartlett. He is a graduate of the Columbia University School of Law, where he was a Harlan Fiske Stone Scholar. He received his undergraduate degree magna cum laude from Brown University, where he was elected to Phi Beta Kappa.

Mr. Ginsberg is a member of the Board of Directors of the John F. Kennedy Library Foundation; the Newseum, the national news museum; New Visions for Public Schools; and New York Cares. He is also a member of the Council on Foreign Relations.

Mr. Ginsberg lives in Manhattan with his wife and two sons.

Clips from This Episode

• On his early friendship with John F. Kennedy Jr.

• Reflecting on his time working with Rupert Murdoch

• Looking back on his early work with the Gary Hart presidential campaign

Episode Transcription

Alan Fleischmann

You're listening to “Leadership Matters” on SiriusXM and leadershipmattersshow.com. I'm your host, Alan Fleischmann.

I'm here with Gary Ginsberg. There are many titles that I can assign to my friend Gary: former Clinton administration official, communications executive, author, public servant in many ways, and a great thought leader. He's a seasoned lawyer, political campaigner, truly one of the great executives in the world, and a friend. Gary has held senior communications positions across a variety of companies, including News Corporation, Time Warner, and SoftBank. An alumnus of multiple political campaigns, Gary worked on Bill Clinton's 1992 presidential run and went on to serve both in the White House and in the Justice Department.

Over the years, Gary has worked to help bridge the gap between Wall Street and Washington, building uncommon tables and connecting two worlds that often speak different languages. More recently, Gary's become an author, last year publishing First Friends, an exploration of presidential confidantes and the significant role they play in shaping the course of American history. He's an advisory board member for the Genesis Prize and is also a member of the Council on Foreign Relations.

Gary is an extremely talented, thoughtful leader. I'm just thrilled to have him on here to talk about his journey, get some of his insights, and share some of the advice that he would want to share from his extraordinary career.

Gary, welcome to “Leadership Matters.” I'm so glad that we're finally doing this.

Gary Ginsberg

I am too Alan, and thank you for that most generous introduction. I think my sister, who is a seasoned lawyer, would take exception to that description of me and my very brief, undistinguished legal career, but thank you for that.

Alan Fleischmann

I bet she’d probably agree with everything else.

Gary Ginsberg

Totally not. Older sister, not a chance.

Alan Fleischmann

So why aren’t we doing this about her?

Gary Ginsberg

Exactly.

Alan Fleischmann

So there’s you and your sister. How many siblings were there?

Gary Ginsberg

I had two sisters, I was the middle child. Grew up in Buffalo, New York.

Alan Fleischmann

And your dad was a longtime lawyer.

Gary Ginsberg

My dad was. That’s very good Alan, you've done your research. My dad was a longtime lawyer. My sister and I were both inspired by my father's practice. He was a sole practitioner for a long time, then joined a firm later in life, but just loved the law. Lived and breathed the law, worked six-and-a-half days a week. Took on clients big or small, guilty or not guilty. Just loved to represent people and took it quite passionately.

So he inspired both of us. My sister then ended up going on to have a very successful career, still practicing in Seattle, Washington. I had a very brief, three-year career on Wall Street working for Simpson Thacher and quickly got out to go work for the Clinton campaign. That was the extent of my legal career.

Alan Fleischmann

And what about your younger sister?

Gary Ginsberg

She is an English professor out in Oregon. She and her husband both got doctorates in English from the University of Buffalo, State University at Buffalo, and went out to Seattle to teach for the University of Oregon.

Alan Fleischmann

What did your mom do? And tell me, how did y'all get to Buffalo?

Gary Ginsberg

My grandparents came over on the proverbial boat, ended up going from Ellis Island and just headed north. They had cousins in Rochester who were working for Eastman Kodak. They made it a little bit further west in Buffalo in the 1920s.

My parents were both born in Buffalo, stayed in Buffalo their entire lives. My mom is still living there, a complete diehard Buffalonian, even to this day she tells me I need to move back to Buffalo. Because things are looking brighter in Buffalo, they're always looking brighter in Buffalo since my childhood, when there were quite dark days in the city. When all of the heavy industrial businesses shut down, beginning with Bethlehem Steel, the city went through just a terrible depression during my teenage years, but I think brighter days actually are finally arriving in the city.

Alan Fleischmann

That’s exciting. Do you get home a lot?

Gary Ginsberg

I do, yeah. I'm quite devoted to the city. Through its football team, but deeper, just because it's a city that's had its hard knocks — for really a century, since McKinley was shot there. But its people have a great spirit, a tremendous devotion to the city.

Alan Fleischmann

I remember the days when Tim Russert was on Meet the Press, was he from Buffalo?

Gary Ginsberg

Yeah. Tim Russert, Wolf Blitzer. The people who've come out of Buffalo and done well have that same attachment to the city, just because I think it is such a great place to grow up. Very family oriented, very egalitarian. People were not defined by what they did or how much they earned, but really, by the quality of their character and their values. It was a really good grounding for me as I left the city and moved here to New York.

Alan Fleischmann

And you went from Buffalo to Brown University, right? Was that a big choice?

Gary Ginsberg

Well, my sister wanted to go there didn't get in. So, given what we were saying earlier, that made it all the more imperative that I get in and go there. So it was an easy choice for me when I got in. But I will say, it was a very large gap going from a Buffalo public school to Brown University. It was a world that I had not experienced before, a world of wealth and kids who were far more advanced in their lives at the age of 18 than I was — who had traveled the world, who had means beyond what I could have possibly dreamt in my youth. Very different from my son, who grew up in New York City, went to a New York City private school, and went there. I think that transition for him was far more seamless than it was for me.

Alan Fleischmann

Yeah. But you met a lot of great friends there too. I knew John Kennedy Jr., and you were one of his dearest friends. You've written about that friendship over the years as well, you did wonderful things with him. I assume Christiane Amanpour was there too? I know she was friends with John.

Gary Ginsberg

Yeah, she went to University of Rhode Island but was a really dear friend to John. Spent a lot of time with him and actually was his roommate his senior year, that's how I got to know her. He was a great friend and I miss him to this day.

Alan Fleischmann

And you've written about him, right?

Gary Ginsberg

Judiciously. I didn't write a book, I decided I didn't want to take that path that so many others did. I wrote an essay about him based on an experience that we had when we went to interview George Wallace, in 1995, for the main issue of George. John made the centerpiece of the magazine the John Kennedy interview and we chose George Wallace as his first subject. So he and I crammed for a month, we read all kinds of books on Wallace. We went down to Princeton to interview Nick Katzenbach, whom you may remember, was a deputy attorney general who stood at the doorway alongside Wallace, trying to get him to move aside to let in the students.

So we went down there for four days to interview George Wallace. It was a really remarkable experience. So it was one of the anniversaries, I guess it was the 10th anniversary or 15th anniversary of John's death, that I wrote a brief essay about a certain night that we experienced together there.

Alan Fleischmann

I’m gonna go back to George in a little bit, I want to talk about that. Because for those who don't remember it, it was groundbreaking. It did transform journalism, I would argue, because a lot of doors were opened because of George. You guys saw something that people didn't see. There were like two sides: there was the Vanity Fairs and certain magazines on this side, then there were these very hardcore political analysis kind of magazines on the other end. John, you, and team with George were like, “You know what, people are looking at the world differently. They're digesting news differently. They want to be read to differently.” And out came George.

Gary Ginsberg

That is exactly right, Alan, you got it dead right. Dividing that world between the Vanity Fairs and the New Republics was really the reason, at the end of the day, why George couldn't ultimately succeed. Advertisers couldn't quite place it within that vast spectrum. Was it a Vanity Fair, where you're going to command very high CPMs? Or are you a black and white political magazine — although not black and white — where we're not going to want to put a fragrance in it?

So advertisers were really bedeviled by it all, and ultimately, kind of took their dollars elsewhere, to the more conventional route. But to your point about the editorial, it was it was ahead of its time, because John saw something in the 1992 campaign that I think was very foresighted: that politics and culture were really intersecting in a profound way in the early ’90s. He wanted to capture it for a much broader audience than would normally read a political magazine. Political magazines, at that point, were always black and white, were 80% read by men, and were either left or right. He thought politics was too important to be consigned to that small sliver of the American populace, so he decided to make it a four-color magazine, geared as much to women as to men, and to approach politics from a far more accessible perspective. That is not going deep into issues, but by getting to the issues through people and process, through personalities, through vivid depictions of the players and the people behind the players, who were who were driving the agenda in Washington and in state capitals.

It was a great success early on. We sold a million-two copies in our inaugural issue with Cindy Crawford on the cover, we had a lot of momentum early. But as I said, the advertisers eventually just couldn't quite get their arms around it. The cognoscenti in Washington really resented it, because it broke a mold that they were very comfortable residing in and it challenged their hegemony in the coverage of politics. So there were those, you know; the temple of commentators who went after us and hurt us with some of the elite that were driving sentiment toward the magazine.

But looking back on it today, 23 years later, I think John would be quite proud of what it accomplished. It did bring a lot of new people into the game of politics and I think it really did awaken people to all those intersections, how popular culture and politics intersect in meaningful ways. For me, it was just one of the great two years of my life, working with him and working on a startup that had such a profound impact on the world in that brief moment.

Alan Fleischmann

It was amazing. It's amazing when you look back and think about how many things that did transform. It was pre-social media, but when you think about how so many of the digital platforms speak to this intersection, of the personality as well as the policy, that seems to be our normal way of living. It was not our normal way of living until George.

Gary Ginsberg

Yeah, exactly. And I think for John, what was interesting was, when he watched the ’92 convention, he was reminded of his father's ’60 convention in LA. He didn't know his father, he was only three when he died. But he had been kind of brought up by Dave Powers and others who are close to his father and regaled with stories about his father's career.

I think one of the more vivid stories that was recounted to him was the week in LA and the confluence of Hollywood and Washington that came together that week. For him, watching Bill Clinton — the first postwar president to capture that same excitement and magic, that same confluence of celebrity and politics — to him was, “Okay, this is my dad reincarnate. I've got to somehow capture that in something that's going to live.” That's really the genesis of George.

Alan Fleischmann

The youthfulness, that it was a generational change. From George Bush to Bill Clinton was, you know, a World War II veteran to a guy who was really just slightly older than John F. Kennedy when he was president.

Gary Ginsberg

Exactly right. And not dissimilar to his father taking over from Eisenhower. Same thing.

Alan Fleischmann

We'll go back to George in a little bit, because I do find that I think about it a lot. I have the inaugural issue somewhere in this house, I kept it.

You guys sponsored things, that was another thing you guys did which was amazing. You didn't just use it as a publication to read, it became a convening. When you think about the things that you guys did that brought people together with George, under that name, that's also the norm now. When you look at all the major publications and how their lifeblood is often not just readership, but it's also what they do to bring people together. You guys were, I think, the first to do that as well.

Gary Ginsberg

We had huge convening power, obviously centered on John, and our parties were must-attend parties. We had a party at the Chicago convention in ’96 that was shut down by fire marshals about 10 minutes after it started. It's funny, the generation behind us has no appreciation for who John was. But in his day, he was like Princess Diana.

Alan Fleischmann

I was just gonna say that. There were two people in the world, both died within two years of one another, that had a worldwide draw that you probably hadn't seen since Bobby Kennedy. That was John and Princess Diana. A phenomenal draw.

I remember being with him in Chicago, I remember being with him in other places… I was with Kathleen, being at other events with other members of the Kennedy family. Two things were stunning: how many people would come, how many hundreds and hundreds of people were coming out to see him, but also how humble he was, how grateful he was. He handled it with a grace that I don’t think anybody could have done.

Gary Ginsberg

That's what I wrote about when I referred earlier to an event in Alabama. John and I were driving back on a roadside, and our two hosts had said that they were going to have a small dinner just for the four of us. As we approached the roadside inn where we were going to eat, there were literally hundreds of cars on the road as we pulled into the restaurant. John and I immediately knew what was up, these two hosts had invited their 300 closest associates and friends.

So John sat in the back of the car and said, “I'm not going in, this is bullshit. This is completely taking advantage of me.” The host went in, I told him to leave the car. John and I sat in the back and I said, “John, you have to do this. You know you have to do this. There are 300 people in that little roadside inn who are here to see you, whether you want to do it or not. I know you're tired. I'm tired. You’ve got to do what's right.” So he put on a tie, marched in, and for the next two hours, with his grace, charmed everybody in that restaurant, took pictures, and everybody went home so thrilled to have met John Kennedy.

That was just a just a small sign of the grace that you just referenced. He had it in droves.

Alan Fleischmann

He had a generous spirit, almost like he realized that was part of his destiny.

Let's go back a little bit as well, because you, after your senior year in college, became part of the advance team in Gary Hart's 1984 campaign. That's another legendary campaign, I would argue, where so many friendships were forged that still exist today. He was running against Walter Mondale at the time — the former vice president — and was certainly a dark horse. What drew you to his campaign rather than Mondale's? Was it a similar generational change there, as well?

Gary Ginsberg

Well, it's funny, Mondale's son Billy was a classmate of mine at Brown and a friend. He had been trying to get me to work for his father's campaign. But I had a very good friend from Buffalo who was doing field in New Hampshire for Hart from September of ’83 on. When Hart won the New Hampshire primary in an upset, he called me at one in the morning and said, “Hey, I'm leaving New Hampshire to go on the road. You want to join me?” I'd graduated from Brown a semester early and was writing for the Providence Journal-Bulletin, was a full-time writer at that point. I did not want to miss the opportunity to join this bandwagon. I upped and left, told the Journal-Bulletin I'd written my last article, and next thing I knew, I was in Buffalo, New York, with no training at all, advancing an event that Gary Hart was doing at Canisius College.

It was, I have to say Alan, the most thrilling campaign I ever worked on. For those five or six weeks — until the Super Tuesday primary, when “where's the beef?” from Walter Mondale prevailed and he was able to kind of overcome this insurgency — we thought we were we were leading the crusade to take over the Democratic Party. The youth were going to take over the party, to your point about this generational change.

Gary Hart was an incredibly impressive, if odd, candidate. Hard to penetrate, but he had an intellect that was as good as any I've encountered in politics. He had a depth of conviction and a depth of understanding of the issues that is rarely seen in politics. I think we all just felt like we were part of a movement that was going to change America. Change the party, then change America. It wasn't to be, but a thrilling ride for those few months.

Alan Fleischmann

And you were there for the whole time, obviously a huge disappointment.

Did you go right from there to law school? Was law school in your plan already?

Gary Ginsberg

Yeah, I had applied to law school in the fall when I was still at Brown. I had the chance to go work for the Mondale campaign at that point, but I had been admitted to Columbia. So I started law school that fall and missed that general election campaign.

Alan Fleischmann

You missed, I guess, what would have been a big gap if you hadn't had that law school opportunity.

Gary Ginsberg

It was hard to get excited about. When Hart lost, I think a lot of the elation of the campaign was lost for many of us.

Alan Fleischmann

What roles did you play after… Well, so you went to Columbia. Obviously, I shouldn’t miss that part — it’s a big deal, especially in your family where you had so many lawyers. You went to Columbia and you got your law degree.

Did you work on anything in politics while you were at Columbia? Because I know you joined the Clinton campaign.

Gary Ginsberg

I joined the Gore campaign in 1988. So, I was going to work for Gary Hart again. He had every intention of running and I had every intention of working for him again. So in my third year of law school, I interviewed for law firms, but I told them I was going to take a year off to work on the campaign. And that's the year of Monkey Business, so I got drawn right into that, right into the center of that. So obviously, the campaign… Well, I'm happy to tell you. He came to New York for that week, where he gave that speech to the Newspaper Association.

Alan Fleischmann

Where he said, “Follow me?” Or not that one.

Gary Ginsberg

No, no, that's the event, right? Where he said, “Follow me.” They followed him, they discovered that he had Donna Rice in his townhouse, though it’s never been proven that he actually had an affair with her in the townhouse.

Nevertheless, he was he was basically drummed out of the campaign. I had to then look for a new campaign, since I had taken a deferral from my law firm. That's how I ended up working for Al Gore.

Alan Fleischmann

How long did you work for him?

Gary Ginsberg

From August of ’87 until he withdrew in April of ’88.

Alan Fleischmann

So that was an interesting campaign, too: Joe Biden was running, a bunch of people were running during that.

Gary Ginsberg

Yeah. Joe Biden withdrew early, because of the Neil Kinnock plagiarism charge. Interestingly, Al Gore started out as a real dark horse, but ended up in the final three with Jesse Jackson and Mike Dukakis.

The three of them really squared off in New York, Ed Koch was taking Al Gore by his hand. It was not a very good sight for either man, didn't help either one's political career by looking like toadies to each other. He came in a very weak third, withdrew right afterwards, and then I decided to stay on the campaign and I worked for Dukakis through the ’88 campaign.

Alan Fleischmann

At some point, you just kept going, I love that you did this; I got involved with Dukakis a little bit then. But it's amazing how you kept going. As a Democrat, you had a few losses and you just said, “I'm gonna go to the next one.”

Gary Ginsberg

You felt the same way, right?

Alan Fleischmann

Of course.

Gary Ginsberg

If you worked in politics in the ’80s, it was just one disappointment after another. I mean, none of us who got involved in politics beginning in 1980 had any sense of what it was like to win a race of meaning. It was the era of Reagan and Bush, it took a lot of resilience to want to keep getting back on the horse.

Alan Fleischmann

Kind of looking at your playbook and saying, “How can we do it differently, what’s going wrong here? Why isn't this working?”

Gary Ginsberg

Right, exactly.

Alan Fleischmann

But then you signed up with the Clinton campaign. Was that after you went to the law firm?

Gary Ginsberg

Yeah, I was at the law firm. I was in my fourth year and I got a call from the former scheduler of the Hart campaign, who is now the scheduler for the Clinton campaign, saying, “Hey, would you come down a Little Rock and start an advance team for me? We don't have an advance team.” It was January of 1992. He had announced in October. I was in my fourth year, really going nowhere at Simpson Thacher, finding that I wasn't terribly interested in the law and looking for any exit. This was my exit.

I actually got the first leave of absence this 150-year-old law firm ever granted a lawyer and I decamped to Little Rock with a duffel bag. I got there the day that Gennifer Flowers was having her press conference at the Waldorf Astoria to play the tapes of her 11-year affair with the governor of Arkansas. So, I literally get there after she's gotten off the podium, and I'm thinking, “Do I unpack my duffel bag or not?” Because the campaign was thrown into absolute chaos by that revelation. It seemed, with the tapes, that she had the goods. But the governor was masterful in getting himself out of that. I unpacked my duffel bag and I ended up staying in Little Rock for two months to put together the first advance team for Bill Clinton. I had an advance school, I hired the first 12 members, many of whom went on to brilliant careers with the President.

It was fascinating, really encouraging, and fun for me to see how well this initial class did in their lives as a result of that advance school. That was probably my best contribution to the Clinton administration, was finding these young college graduates.

Alan Fleischmann

And one of the first advance schools, really. Right? There was no there was no such thing as an advance school before, maybe not on the Democratic side.

Gary Ginsberg

Actually, I stole the idea from the Dukakis campaign in ’88. The Dukakis campaign in a very proper one, unlike the Hart campaign, which had a kind of facsimile of one. But the Dukakis campaign was very well run and did it.

Alan Fleischmann

When you think of it, a lot of great alums of advance came from the Clinton era. Who went off and actually figured out a way to translate that in the private sector later on in life, as well.

Gary Ginsberg

Yeah, there's dozens, actually, who have done very well with that. Because look: advance teaches you a certain moxie, an ability to think quickly on your feet, be creative, be able to speak to power. You have to kind of act beyond your years, you have to have a certain wisdom beyond your years to succeed. Because you're dealing with elected officials, dealing with fragile egos, and telling them who can introduce and who can’t introduce, where you're gonna sit, all the kind of optics that matter.

Alan Fleischmann

You have to say ‘no’ to people. A lot of noes.

Gary Ginsberg

A lot of noes. You're imbued with all this power at a very young age and you have to learn how to exercise it judiciously and in a non-obnoxious way so that you don't leave town with a lot of detritus. It's a skill that you either have or you don't.

Alan Fleischmann

That's amazing. It's a skill that anybody can use. Also, asking the right questions, anticipating and pre-empting risk, all that.

So then, Bill Clinton wins. You go into the White House. We have the White House before the Justice Department, right?

Gary Ginsberg

Yeah. Well, I had left the advance operation to go up to Washington to vet vice presidential candidates. I spent three months, just after the governor secured the nomination, vetting Al Gore, essentially. He was my candidate. I did a deep dive into his life and produced a number of memos to Clinton and the senior team in Little Rock about the pros and cons of nominating him.

I write about that in my book quite extensively in my prologue, which was part of the inspiration for my book. So I became somewhat of an expert in vetting — to the extent that anyone could be an expert in vetting — along with a group of other lawyers. Many of whom you know, Alan. We became a kind of team that was then reprised during the transition to do it for the cabinet. Then I continued to do that in the White House Counsel's office with a number of them, where I vetted Ruth Bader Ginsburg for the Court. As well as all the senior Cabinet and Administration officials.

Alan Fleischmann

That's amazing, actually. People don't realize that one of the most attractive parts of Al Gore becoming the running mate was that he was the opposite of logic, which made people look at Governor Clinton so differently. People looked at him and said, “You're not trying to do the traditional.” They were the same age, practically, he was a little younger. Both from the South. They both represent so much of the same, it just was the opposite of any playbook prior to this campaign. It showed a freshness and it made people trust him, that he was going to do the right thing, I think, rather than just do what was popular.

Gary Ginsberg

That is exactly right. That is exactly what I wrote in my first memo. In fact, it's funny; Warren Christopher headed up our team and at our first meeting, in the back room of the of the Willard Hotel, he asked us to say who we would support, who we wanted. I said Al Gore, and he looked at me with the most skeptical look, like, “Why would you want to do that?” Because that would upend the playbook that you just described, Alan. I said exactly what you said, which is, we need to reinforce all the all the assets that Bill Clinton is bringing to this race. Youth, vigor, moderation. So, that was that was really the theme of all of my memos down to Little Rock.

Also, I thought that he alone of the really serious candidates had run already, had been vetted. Kind of the same approach that Biden took to Kamala. Why did Kamala ultimately emerge as the victor? Because you took no risks. One thing you learned living through the ’84 campaign — and even the ’72 campaign — was, you do not want to pick a vice presidential nominee who, in the immediate aftermath of the announcement, causes problems because of missed background checks. Whether it's taxes, fidelity issues, health issues. So we knew that Gore had gone through the gauntlet of a very serious vet in ’87 and ’88. I had done enough vetting from ’88 to ’92 to know that there would be no questions asked about his background.

So for the reasons that you cite, plus the kind of sanitized background, I think it was, at the end of the day, a pretty easy choice for the governor.

Alan Fleischmann

Yeah. But it did change… you've done so many things that I think you should get credit for. Being part of things that changed the way we do things after that. It liberated the way people could appoint or select their vice presidents. It was no longer like, “Okay, we're on the East Coast, we need someone from the West Coast. We need this, we need to bring balance here.” It really became down to the person. And again, it was this new era of people versus politics: is the person going to add? I think if you have a bad vice presidential choice, it hurts you. But you never fully understand, comprehend, or appreciate what it does to a campaign when you pick the right one.

Gary Ginsberg

You're exactly right. It's funny, we went on a bus trip right afterwards and I really wanted to accentuate that very point that you're making. There was a football that was in one of the buses, and I said, “Hey, when we get to the next stop…”

Alan Fleischmann

And that was the bus tour with Hillary, Tipper, and Al…

Gary Ginsberg

Yeah, the first, one, where we went to St. Louis. So I said, “We should have the two of them throw a football when we get off this bus.” We were doing some stupid event, and I said, “I'm telling you, if you really want to bring the youth and vitality of this ticket, let's just have them toss the football back and forth. It'll make them so accessible to the youth vote, it’ll look so hip.” Could you imagine Lloyd Bentsen and Mike Dukakis tossing a football? Or Lyndon Johnson and Kennedy? It doesn’t work. George Bush and Ronald Reagan?

It's funny how those little moments can have a real lasting impact. But I think the voters really did gravitate to this sense of generational change, just the vitality of this pairing and how telegenic they were together.

Alan Fleischmann

And television was changing its news reporting so that it was more 24/7. It was definitely covering more stories about the people, not just the policy. That exchange — the magazine photos, seeing it on TV… Throwing the football between the two was much more powerful than if the two of them just got up there and said, “Hey, we're both young and we're friends.”

Gary Ginsberg

You know the saying. Show, don't tell.

Alan Fleischmann

Exactly, exactly. But I really do think the choice of Al Gore — we still feel it — was such a profound choice. It's really one of the main reasons why he won. I think it changed the way people look at running mates ever since.

I don't think there would be a Joe Biden today… I think the same thing happened. Obama didn't pick Delaware as a great place for him to get more votes. He chose a person who was going to be the antithesis of what would have made sense in any old-fashioned playbook, which was refreshing. And he sent a message. I’ve got a seasoned, Washington-experienced uncle or godfather, if you will, that will join me on this road.

Gary Ginsberg

Exactly right. The tragedy of the Gore-Clinton relationship is how it ended. I mean, I know you know it as well as I do. It was a bitter falling out that has never really been repaired.

Alan Fleischmann

It's a sad thing. I mean, Al Gore has probably had the best post-vice presidential career of any vice president by far, he’s almost considered to be a former president. But it is sad how it ended. A little bit had to do, I think, with the wives also, how it ended.

Gary Ginsberg

Yes, yes.

Alan Fleischmann

It makes reunions a lot harder, I'm sure.

So tell us tell us a little bit then: you're now in the administration. You went and did all of that, you were part of the Al Gore choice, the campaign becomes a success. Then you go into the White House first, to the counselor's office. Which is a great continuity from where you were just before.

Gary Ginsberg

Yeah, and you've just reprise the role. I basically became a professional vetter. I did that, I worked for Vince Foster. Then when Vince died, I really wanted to go to the Justice Department. Vince's sister was an assistant attorney general. So in the fall of ’93 — I was at the White House for nine months — I went to the Justice Department, where I basically worked as a special counsel to legislative affairs and antitrust, spent a lot of time doing antitrust policy with a woman named Anne Bingaman, whose husband was Jeff Bingaman.

It was a really interesting year of doing law and politics, which was kind of what I wanted to do. Then I went back to New York, because I got married.

Alan Fleischmann

What did you do in New York when you came back?

Gary Ginsberg

I was initially going to work for Ron Perelman as his chief of staff, I was recruited out to take that job. And before I started, the person who was in the job, who was supposed to go to an operating company, ended up staying in the job. So they gave me a year for my troubles of going back up to New York. That's when I ended up going to work with John at George. It was very fortuitous.

Alan Fleischmann

I love all these things in the way they happen to you. I mean, it's obviously your gut. At this point, you've already built a great reputation.

But there is a fabulous thing in life… I tell this to people all the time and we talk about it on the show a lot. We're all about planning and strategy, you and I. We’re big on figuring it out. But it's not to come up with a strategy that becomes your hardcore blueprint. It’s strategy so that you can see opportunity when it's there, that you may not see if you don't identify it beforehand.

I think people look at strategy and life as, “I'm going to do this for two years, I'm gonna do that for a year, I'm gonna do that for three years, this is how I'm gonna do my life.” It doesn't work that way. It's really just identifying, asking yourself questions so that you can open up to opportunities when they do come forward and say, “Does this fit in what I want to do?”

Gary Ginsberg

Very, very wise. Just to encapsulate that, somebody in my late 20s said to me, “The way I've lived my life is, my first 35 years, I wanted to accumulate as many interesting experiences as I could and figure out during those experiences what I was really good at. Then spend the next 20 years doing that and amassing whatever you need to. Then, at 55 or 60, go back to accumulating as many more experiences to live out the rest of your life.” And I found that to be such an interesting organizing framework for my career. It's kind of how I ended up living my life, was to just… To your point, I didn't really have a, “I'm gonna do this, then this.” I was very open to new opportunities and willing to take risks. Which I think, you know, is not for everybody. But the willingness to get off of a track — and I was on a very specific track, going to law school, going into a big law firm. Everybody then stayed relatively on that narrow track. They may have deviated to an investment bank or to a consulting firm, but they put on a suit every day, they went into an office, they worked with grownups, they handled big matters, they made a lot of money.

When I went to George, I completely deviated from that. I was now working in a t-shirt with my friends, with people who were two-thirds my age, in a startup with a very uncertain future, making no money at all. But it was transformative. I learned so much from that experience, it was exhilarating. Little did I know that how much it would set me up for the things that would come after.

But it's not for everybody, and it's not like I made this transition without any fear or sleepless nights. I had all that.

Alan Fleischmann

You also worked all the time.

Gary Ginsberg

You work all the time. I worked as hard as my law firm colleagues who were making five times, six times what I was making. But I promise you, I was more were invested, I was more exhilarated, and I felt better about my work than any of them did. That I'm sure of. Nevertheless, it does take a strong constitution to be willing to do that.

Alan Fleischmann

It’s that. But it's also… I'm all about measuring things, metrics, all that. But I always push back with friends and clients in life about over-measuring. It's not the number of hits, it’s not that you came up with, “I want to do four things on Thursday, we do eight things on Sunday.” It's really identifying where there may be opportunities, so that you can both organically and inorganically identify them, make them happen, curate them.

I don't believe you should just sit back and let the world come to you only. You’ve got to sit up. But let yourself see opportunity. You would have never seen the opportunity in George, for example, if you hadn't felt that it was something that you could actually join.

Gary Ginsberg

Sure. But that takes courage. It takes faith.

Alan Fleischmann

It does. It takes risk, it takes faith, but it makes your blood move a little bit faster, makes the adrenaline become more ever present. So it's probably not a bad thing.

Is there anything in that George experience that you have regrets about? Are there things were you say, “Gosh, I wish we had done that.” Obviously, with John's death, it's a whole different thing. But looking back on the professional side of the George experience, are the things you think, “Gosh, if we had done it that way, we could have done it.” Or is it really — which is what I think — that you were ahead of your time?

Gary Ginsberg

I think it's three-quarters that we were ahead of our time, and one-quarter the fact that we probably had the wrong corporate parents. Had we been in a stable of magazines that were more established in throwing off more revenue and free cash to support a startup as daring as George, we probably would have been better funded and able to afford better writers. I mean, we did a lot on a very tight budget. And as the advertising dollars dried up, Hachette’s support for it dried up. It just had this catalytic effect on our ability to increase readership through better content. I think that was more a function of… Very few of the established publishing companies kind of got George in 1993, 1994. It took a guy like David Pecker, who was a swashbuckling head of Hachette, to make the initial investment. But I think over the long term, they were probably the wrong one.

Alan Fleischmann

You went from there to News Corporation with Rupert Murdoch, right? That had to be a little controversial for your life, I imagine.

Gary Ginsberg

It was. I think a lot of people looked at me like a chameleon. I could put nicer words on it. Sell-out, whatever. But it's interesting, because Rupert Murdoch at the time wasn't nearly as much of a lightning rod, in 1999, as he is today. He wasn't as divisive. I mean, he was controversial, because I think the programming was viewed as very downmarket, very populist. Fox News had started, but Fox News was still a blip on the screen in 1999. I actually took the job in 1998. It didn't have character, really, in New York for a long time, so it didn't make any impact. It hadn't really found its voice until the Clinton impeachment in ’98.

So I think for if I were to go to Rupert Murdoch today, it would be a shonda — you know that word. I also could take some comfort from the fact that so many of its assets were based in Hollywood and were quite progressive — you couldn't really fault 20th Century Fox, the Simpsons, Titanic. We had some cultural, iconic programming that was neither left nor right, but just really, deeply popular. In London, he was much more of a divisive figure for having broken the unions, for his role in electing Tony Blair. He was he was much more defined there than he was here in 1998.

Alan Fleischmann

I remember that period, we were there too. You were one of the great bridge builders, I would argue as well. You were there during a time when things were becoming, I think, more divisive in the world of News Corporation and Murdoch. But you were one of the very few people could actually sometimes bring people together, build bridges.

Gary Ginsberg

He hired me, I think in part, because he had been surrounded by a very particular kind of executive up to that point. I was generation younger than everybody else around him. I was a liberal, I was Jewish, and I don't think he had had anyone quite like me. I think at that point in his life, he wanted a different voice in his inner council, was very open to it and welcomed it right from the get go. We just bonded instantly. I could push him, I could argue with him, I could introduce him to things that he was always at least receptive, if not flat-out open to.

I look back on my nearly 12 years there with a lot of satisfaction. That in my time there, I was able to bridge a lot of worlds and do some good for the causes that you and I care about. Maybe that’s defensive, but I think it's fairly accurate.

Alan Fleischmann

You ever watch Succession?

Gary Ginsberg

Of course.

Alan Fleischmann

It’s amazing.

I thought it was a great way to define you, not stereotype you. I thought in some ways, that move allowed you to not be seen as a Democratic operative, or someone who was just a liberal, but someone who actually was an executive. From looking at your journey in your career, it is what made you be seen as an executive in the space that you're in, because you were no longer defined by other labels. You were defined by where you perched. And I think that was pretty important as well.

Gary Ginsberg

Well Alan, thank you. I never actually thought of it like that.

Alan Fleischmann

I think of it.

So you were at Time Warner — I know we’re going to run out of time, I don’t want to dive in too much — and then you were at SoftBank. I'm just curious: when you compare Time Warner, SoftBank, and News Corp, your jobs were similar, I would argue. But the cultures of those three had to be vastly different.

Gary Ginsberg

Vastly different. I think News Corp and SoftBank were very similar in that they had swashbuckling owners/CEOs/founders who are big risk takers, looked at the world as their oyster. There was no opportunity they didn't want to at least look at, if not seize upon. They were wild rides, particularly for me with Rupert where I was sitting by his side for as long as I was. I learned an enormous amount, because I watched his leadership style — and this is about leadership matters. He was a man who just consumed information. Read every newspaper that he published and most newspapers that he didn't publish that interested him. He watched enormous amounts of television and took in so much information to help form his thoughts about opportunities, economic or business opportunities.

Then he would take his counsel on a really on a one-to-one basis, he wasn't much for groupthink. He liked to listen to people, sound them out by phone or in his office, and then with a very small council make decisions that had great import. Oftentimes without the counsel of this board, I should add, because it really was a family-controlled business, which I always found amusing. I'd have to say to Rupert, “Maybe you should inform the board before we go out publicly with this announcement.”

Masa, in the little time I spent with him — which was little, in the two years I was there — was very similar in that. He wanted his entrepreneurs to act crazy, for good or for ill. We saw it for ill when WeWork crashed; in other instances, it was for good. He too had a voracious appetite to acquire, to control, to govern.

Jeff was a very wise, measured, traditional CEO, who understood exactly where the company was when I joined there in 2010 and knew exactly what he needed to do, which was ultimately to sell a business that was in structural decline. He saw, before any of his peers, that we were going to be disrupted by the Netflixes of the world and tried early on, with Brian Roberts, to solve for that with a thing called TV Everywhere. That didn't get any adoption from nearsighted content owners and cable operators. So it was a different kind of time and a different kind of leadership, because he knew in those next six years before we sold to AT&T that we had to divest rather than grow. We had to slim down in order to be to be bought. So I watched a CEO who is very much into convening, into hearing everybody at the table, to having very vigorous debate amongst ourselves in person. An equally effective style that resulted in a very advantageous transaction for shareholders — if not for employees, who had to live through a reign of terror by AT&T over the last three years, now culminating with the sale to Discovery.

Alan Fleischmann

Each one of those experiences were, in many ways, profoundly different journeys. But they all dealt with adversity, they all dealt with challenges, and all that dealt with the changing nature of media.

Gary Ginsberg

Yes, yes. I taught a class at Columbia Business School called “Entrepreneurship and Incumbent Media” because by 2015, the disruption was beginning. ESPN shed three million subs. So a friend of mine and I taught a class where we wanted to instill on young business students that they have to be able to see into the future and see where, yeah, you may be sitting on a cash cow now, but that cash cow isn't always going to exist. Every day, you have to be looking around the corner. Where where's the next threat? How do I anticipate that threat and begin planning for it?

That kind of heightened me to the need for leadership to not get complacent. Jeff, for sure, really embodied that, which was part of the impetus for my wanting to teach this class. Seeing how much he anticipated before anybody else and how he began to change the strategic direction of Time Warner in light of that.

Alan Fleischmann

When you left there, did you know what you wanted to do?

Gary Ginsberg

No, no. I left there in 2018 after we sold the business, we got challenged by Donald Trump. I thought I had one more play in me, I was gonna go work at the NFL actually and was offered their chief government communications job. I just wasn't sure I wanted that kind of intensity again. So I didn't take it, but SoftBank then came and I thought, “Yeah, I got one more in me. This is totally different than anything I've done. It's venture capital, it's $100 billion. It's a swashbuckling CEO again who wants to change the world. Let's give it a go.”

And I did that, really, for a year. I took a leave of absence to work on Mike Bloomberg’s campaign. I just wanted to go back to my campaign roots. So I spent three months working with him, which was a real joy. I mean, it didn't have a happy ending, but I have enormous respect for Mike and when he tried to deal with that campaign. It was unfortunate that the debate turned out the way it did, but it was working with close friends. I know, you know, the team really well. And it was thrilling for me to be back in that game after so long.

Alan Fleischmann

Yeah. And then, what was your plan? Was the book already in your mind?

Gary Ginsberg

Yeah. I always wanted to write a book, Alan. I wanted to write a book on chiefs of staff in 2012. I started doing research, I talked to an agent, she said, “I can sell this.” But I was in the throes of Time Warner, I just didn't have the time.

But in 2018, after I knew I was leaving Time Warner with the sale, I came up with this idea of First Friends. I called that same agent, and she said, “This time Gary, you cannot let this go away. This is too good. You've got to write a proposal, we've got to get this sold.” So I finally got my act together and sold it. I wrote the proposal beginning of 2019. We sold it quickly and I had until the end of 2020. Of course, I started doing work on it in 2019. I was working at SoftBank, working on the campaign, but I was making slow progress. Then when the pandemic hit in March of 2020, I basically went into a hovel and just devoted my life to it for the next 12 months.

It was one of the thrills of my life to do something completely different from what I had done. I had lived this world of external affairs, I was kind of the face, and every day was filled with lunches and dinners and meetings. Being out and about, as I know you are so familiar with. Suddenly, I'm just sitting alone with my computer, my phone, my books, and just reveling in it, just loving it. Because I was living with my heroes from the past, I was creating something tangible every day that, at the end of the day, I could say, here's what I did.

At a certain point, I kind of got the voice. And once I got the voice, I knew I could do it. It was just an absolutely satisfying, emboldening year for me, cranking out that book and then seeing its success.

Alan Fleischmann

During covid too. You're such a success and you were successful with this book during the pandemic, also, which is pretty remarkable.

The book itself is amazing. It doesn’t surprise me, you're always doing something where you're seeing something ahead, but it shocks me how we hadn't thought about that. Well, I’ll say it differently, I did think about it. I thought about how you really can't rein in how important the power of a friend is to the president — or anybody, whether it's a CEO or a president, but certainly at the White House. The first one that became so well-known in modern times is Vernon Jordan during that tumultuous period. Vernon and I were close, and I knew so much more about the first friends than a lot of people knew. They have full access, especially under Clinton, but others too. Then you saw that under Obama, Bush, and others as well. But no one ever quite told this kind of story. We talk about first ladies, but we never told the story about the first friends. And you did. I think it's the first one, the first one that certainly went deep.

Gary Ginsberg

Well, there have been books about a first friendship. There have been two, really: Lincoln and Speed was written about, and Daisy Suckling and Roosevelt. But no one had ever put it into a book and looked at a whole series of them through history. I just literally woke up with the idea of one morning and I was like, “Jeez, this is a good one. This one I got to do.” I was lucky to have an agent, who was the same woman who gave me my life advice about 35 to 55. Her name is Esther Newberg at ICM.

Alan Fleischmann

I know Esther. Esther also does Caroline Kennedy's, I met her through that.

Gary Ginsberg

Yes. Exactly. Just legendary. She's phenomenal, and really, without her prodding, I probably wouldn't have gotten off my butt and done it. So I'm immensely grateful to her.

Alan Fleischmann

She's quite a legend.

People might not realize it, but I thought of it reading the book, it's a little biographical for me about you and about anybody who's had a position where they are the trusted confidante. While that's not said, you could relate to the need for this president to have that person, who is going to tell you what you don't want to hear, and is going to be there to hold your trusted secrets and help you make decisions. That's a role that you've played throughout your entire career, both in politics and in the private sector. I can imagine you felt an affinity and a connectivity to those roles, because it's a role that you've played. And everybody needs it. It's what I do for a living everyday, too. This idea of the confidential consigliere, the adviser, the friend, the trusted person, the opposite of the yes man.

Gary Ginsberg

That’s exactly right. Without self aggrandizing, I think part of why I was so drawn to this was my experience at George. Because John started this magazine, and he was, you know, fearful. It was as if this was going to be his coming out party. He didn't want to be defined by being a DA. He wanted to be to be defined by this magazine, so he didn't want it to fall on its face. So he's starting to put together the business plan, he brings me into it, I help him write it.

And then when he starts it, I think what he really wanted was a friend around him, who could just kind of have his back. Because he's bringing on all these outsiders whom he doesn't know. Being him at that time, it's daunting to be surrounded by people you can't really necessarily trust yet. You don't know if they're gonna sell you out, you don't know what their ultimate objectives are. So I think he just wanted somebody who he felt comfortable with, who could tell him what was up, what was down. To decipher what was going on in a room in a way that he could understand, to have somebody to blow off steam with, and somebody to just tell him the hard truths when he needed to hear him.

I wasn't a magazine editor, hardly. I wasn't really a writer. But I think he just wanted that role around him constantly, to how to provide those twin functions of emotional ballast and substantive truth to help him through those early years. We spent as much time playing frisbee in mid-afternoon, because he needed to blow off steam and I needed to blow steam, as we were sitting in his office debating story ideas and whether he should fire an editor, or do a story or not.

So I guess I kind of, in a way, saw the role, even though he obviously wasn't a president, may never have been a president. But I just appreciated that role in a sense. I was not his first friend — he had closer friends than I was. But it was, in a sense, playing that function. I think that's part of what was motivating for me about this book, was seeing how it played out for him.

Alan Fleischmann

Certainly, he had a distinct category in life because of who he was and then who he became. I think in many ways, he was a public statesman and were playing that role. So it doesn't surprise me, also, that your first instinct for a book years earlier was on chiefs of staff and then you went off to first friends. Because at the end of the day, they can hold the same role.

When you look at your career and you see what you did in your career, it is that person you go to for common sense, good judgment, who isn't weighing things based on their own professional journey or their own ambition, but they actually put you first. That are willing to say, “Let's talk through the risks, let’s mitigate them; let's talk through the opportunity, let’s weigh them.” They help you make a decision. That's pretty profound.

The person in the front row is the one that gets to be recorded in history, often. What your book does, it expands that history. So that you know — whether it's chiefs of staff or first friends — that so much of history is made by the people, that trusted few, who were around that principal. That's something that we don't tell enough in history.

Gary Ginsberg

That was well said. I chose not to do chiefs of staff because I didn't want any staff to be in the category of friend. Because even with a chief of staff, there's a limit to just how blunt you can be. I think Mack McLarty probably ran up against that as a childhood friend. I think substantively, for him, it was probably a little bit far afield from what he was used to.

But I think for Vernon, he had no governor. He didn't need to have a governor because he didn't need or want anything from the president. His job was not dependent on his friendship with the president.

Alan Fleischmann

It affected my journey, because I always felt like, me saying I didn't want anything in return gave me more opportunity in life to actually be me and to say what I wanted to say at different times during these moments. I think the Vernon example is actually a shining example of how one could do that. With all kinds of things, with CEOs and other leaders, not just presidents.

Gary Ginsberg

Exactly. Then just to add on one other element: discretion. He had impeccable discretion in his relationship with the President.

Alan Fleischmann

Yeah. Being trusted and knowing it's not a person who's going to gossip, he's going to keep it. That's very impressive.

Well, the book is remarkable, I recommend people to read it. I hope that it has many other iterations or even, maybe, sequels to it if you're into doing another book. But it's a remarkable book. It's so enjoyable to read, but in many ways, just like you did with George, you personalized history and it allows you to actually digest history through human beings. Rather than, these are the facts to memorize, the data points to absorb.

Gary Ginsberg

Yeah, I was hoping to do with history what George did with politics, which is to popularize it, make it accessible and an easy entry point for understanding American history. That really was my aim with First Friends.

Alan Fleischmann

It's amazing.

You've been listening to “Leadership Matters” on SiriusXM and leadershipmattersshow.com. I'm your host, Alan Fleischmann.