When a mutual acquaintance introduced Bruce David Klein to legendary activist investor-slash-corporate raider Carl Icahn, the documentary filmmaker leaped at the opportunity. Klein, the helmer of docs on the late rocker Meat Loaf and the MIT blackjack team that took casinos for millions, says he is drawn to subjects that are “over-the-top successful” but whose talents are also “mysterious.” He pitched Icahn on a documentary about his life and work, which led to “a million and one questions” and months of negotiations.
Eventually, Icahn agreed to participate in the project, and HBO’s Icahn: The Restless Billionaire was born. Premiering Tuesday on the network and also available on HBO Max, the film explores Icahn’s life and career while highlighting landmark deals involving companies like Apple, Trans World Airlines, Texaco, Herbalife and Netflix. While Icahn tells his own version of events in the film, the documentary also canvasses journalists that have covered the 85-year-old for years about the good, the bad, the controversial and the contradictory in his career and legacy. In the view of some sources, he has sometimes crucially exposed management excesses and boosted shareholder value. Sources also resurface criticisms that Icahn’s takeover attempts have led in some cases to job losses and labor issues and that he’s amassed billions — this year Forbes estimated he is worth over $16 billion — by raising value in the short term without taking longevity into account. (His time as a non-salaried Trump White House adviser, which The New Yorker has reported was characterized by potential conflicts of interest that Icahn denies, is not addressed in the film; Klein says he asked Icahn about the role but “getting drawn into a highly charged ‘news cycle’ type political sidebar story — when politics is not actually a big part of what Icahn is about — seemed like a detour on our path to probing his unique DNA.”)
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In Klein’s view, one key takeaway from the film is that “if you have a problem with what Carl does, you should look to the system.” Before the premiere of his documentary, The Hollywood Reporter spoke with Klein about what the financier’s story says about “our current expression of capitalism,” Icahn’s reluctance to talk about his personal life and what it was like to debate interview questions with the takeover artist.
How did the idea originate for you and how did you get Carl Icahn and his family involved — was that a challenge?
Yes. Basically, after I was introduced to him through a mutual acquaintance, I kind of presented him this idea of a feature documentary on his life and work. And we went back and forth for many months, you could even argue over a year, about the “life” part of that. He immediately got the idea of, and I think was interested in the idea of, going deep into his deals to really understand his strategy and the choices he made at various points in negotiations on these huge deals that really changed American business history — things like TWA, Texaco, Netflix and Apple and Blockbuster. I think the idea there was, Carl, people will naturally be interested in you giving insight into your deals and that’s great, but people also like to see the 360 [degree] view, they want to see what you’re like personally. What are you like every day, what do you read, what do you do, what’s your favorite flavor of soda? All of that stuff is something that I become obsessed with whenever I do a film like this. And he was reluctant at the beginning: “No one’s interested in seeing me playing tennis, why do people want to see me having breakfast with my wife? People aren’t interested in that.” And I had to convince him over time that, actually, when people see an interesting business deal unfold and the person behind it, the thing they immediately want to know is how did the person become that person?
And interestingly, contrary to the common perception of Carl as a kind of my-way-or-the-highway-type guy, he really enjoys the debate. There were lots of phone calls, lots of meetings, he asked a million and one questions. One of the issues was he doesn’t really watch documentaries so it was kind of tough convincing him. But eventually I think I convinced him that people who watch documentaries hunger for both the life and the work. From there, that’s how the film really developed in terms of the film you see now.
How much time did Icahn give you to do interviews and to follow him around in his daily life? Did you have much freedom to observe or was your time together more structured?
By the end, we were with him over 100 hours over the last couple of years. We shot at his office, at his apartment in New York City, at his house in Miami, in East Hampton, we shot him having breakfast with his wife, him going back to the neighborhood where he grew up. This is for me one of the most fascinating dynamics of documentary filmmaking, that kind of push-pull at the beginning with a subject where they are reluctant and want to give you as little as possible, but over time there’s that dynamic that pops up where they realize that it actually may be in their interest to give more rather than less. He’s had 60 Minutes pieces on him and profiles and everything. Once he realized this wasn’t a traditional journalist preparing a single article or five-minute feature on a TV news show, but I was going in really deep, for instance, into a deal he did in 1979, and once he realized that I had studied a lot about his background, his deals, he made himself more and more available.
How did Icahn compare in terms of an interview subjects to past subjects you’ve worked with?
Well, everything with Carl is a debate, it’s just his nature, so even asking a question very often gets the answer, “Well, why do we have to ask that question?” And then it’s like “Well, I need to know this.” And then he’ll say, “Well but maybe this is more important.” “No, Carl, this is important.” So it’s a constant battle in that sense. In tribute to him, there were no questions, no topics that were off-limits. He was totally open. He clearly enjoyed talking about the deals much more than the personal stuff. Having said that, the personal stuff is in the film and I’m sure he would love it not to be in the film, but it’s in the film: You see I think a lot of revealing moments with him, with his family that are very often funny, poignant, sad, powerful, insightful, revealing, all those things, hopefully.
How did other interview subjects who act as commentators, people like Andrew Ross Sorkin and Bill Gates, join the documentary?
Basically I really wanted this to be an intimate film and I did not want to have random experts or journalists who may know a lot about Icahn but don’t really know him. So I kind of had this rule that everybody who would be an on-camera contributor actually had to know Carl. People who cover him, people who have meaningfully interacted with him. Like Bill Gates for an example, wasn’t just a name: He knows Icahn, they talk from time to time, I think they actually really appreciate each other’s minds. Even Oliver Stone, who’s in the film, although he doesn’t intimately know Carl Icahn per se he obviously spent time with Carl, which he talks about while he was writing Wall Street and learned about the new way of doing business in the ’80s, which certainly influenced Wall Street. So everybody had to have an actual connection, intimate knowledge of Carl, what makes him tick, what he’s like in a room as opposed to just a journalist who calls him once in a while for an interview.
Did Icahn want any of those people in particular to really be in the film?
No, I mean, we work very independently of him. So I think the people who are in the film are acknowledged as people who really know Carl very well because he appears on their shows often or they write about him often, and not always positively. So Andrew Ross Sorkin in the film talks very openly about this debate that he has had over the years in his columns over what is Carl Icahn? Is he a vulture who only cares about Carl Icahn and making money? Or is he a shareholder advocate who actually is this beneficial force to make a lot of people a lot of money? So he’s a good example of somebody who has discussed and debated that in his columns and with Carl, and that’s why he was a perfect contributor for the film.
As you noted with Sorkin, some of your sources mention all of the contradictions that Icahn’s story contains — he’s amassed massive amounts of wealth by meddling in companies, he has also created more value for some shareholders, he’s a one-percenter, he’s also a critic of wealth inequality. Did you come out of the film feeling like you had made sense of some of those contradictions, or were many of them still mysterious to you?
That’s actually a really key question. I think a couple things: One is I was fascinated or haunted at the beginning of this process by the question of “do rich people really know better, are they really smarter if they have had outside success, or do we just perceive them to be smarter?” There’s a line in Fiddler on the Roof where “when you’re rich, [they] think you [really] know.” I was fascinated by that question early on and by the end of the film I became much more convinced of his unique DNA, of his unique mixture of the street kid from Far Rockaway and the finely tuned brain, à la philosophy major at Princeton, and that was a very, very interesting journey to go on. In addition, I always when I start a film kind of look at, what are the common things that people think about the subject? And I think in Carl’s case you realize fairly quickly that he is not the humorless, angry, moneymaking machine that most people think of him as. It turns out that he is a man of contradictions: He is absolutely stand-up comedy-level funny and he has a soft side and while he’s absolutely obsessed and driven to make as much money for Carl Icahn as possible, it’s not always for the reason you think. There are often some surprisingly profound philosophical principles that energize a lot of what he does. To capture this is was really about letting the cameras roll at home or in the office, and capturing moments that defy expectations.
In your view, after speaking with sources and working with Icahn, what were the positive and negative effects that Icahn’s career has had on Wall Street?
I think that the revelation is that if you have a problem with what Carl does, you should look to the system. Because people like Carl, the way they see it, they are making money within the system that was created. So our current expression of capitalism is such that somebody like Carl can find these kind of pores in which to dive in and make a lot of money. That’s part of also, to me, the revelation. I think the easiest thing to do is to say he has $20 billion, therefore that’s unfair and he’s not a good person. I think the more nuanced look at it is to probe deeper and say, well, why was he able to make $20 billion and is this a system that we like? What he points out, which is kind of true as you delve deeper and deeper, is that he could not make one penny if every company — and again, it’s not possible — was basically productive and well-run. Then he would not be able to exploit weakness and make money. And so his point is, well, make your companies productive, make sure your CEOs don’t make a zillion times what the average worker does, change that system, and I may not be able to make any money and ironically he’s fine with that. That’s what makes him a contradiction.
This interview has been edited for length and clarity.
