Carl Icahn – corporate raider or activist investor?

How did a kid from Queens in New York go from being a cabana boy to one of the wealthiest financiers on the face of the planet? Icahn: The Restless Billionaire reveals all in one of the greatest examples of The American Dream in action. A prominent figure, Carl Icahn’s name sounds a lot like ‘icon’, which could have motivated him to become one in his quest to build an empire. A master strategist, it’s as if Icahn plotted his trajectory over the course of the last half century, amassing close to 20 billion dollars. The son of a school teacher and cantor, it’s extraordinary that he became the kingpin in some of the biggest business deals in history. 

So what led Icahn to forge a kid and his toy soldiers to untold wealth, and how did he get there? These burning questions were the driving force for writer-director Bruce David Klein, who caught up with Icahn to uncover some of the contradictions that make him one of the most fascinating characters on Wall Street. In one sense, a man with a ceaseless desire to win the numbers and strategy game at all costs and in another, someone trying to poke holes in the system that made him into a billionaire, he represents the best and worst of capitalism.

This focus makes the HBO documentary Icahn: The Restless Billionaire essentially a character portrait of the controversial financier, which chronicles his business triumphs (and even some failures) through insightful case studies and vivid flashbacks. 

Carl Icahn has a sign on his desk that says Master of the Universe – making you wonder if he’s playing or placating a galaxy-sized ego. While the billionaire investor has many mementos and toys serving as tokens from some of his biggest acquisitions and deals, there’s always a hint of seriousness in a joke. Founder of Icahn Enterprises, the “master” has a knack for acquiring controlling stakes in companies and pushing for changes in management and strategy to boost shareholder value. Now a respected activist investor, Icahn’s aggressive business tactics initially landed him the label of corporate raider in the 1980s, specifically during his takeover of the Howard Hughes founded airline, TWA. Whatever your feelings about the high finance bigwig, there’s no denying his far-reaching influence, having had a direct influence on Gordon Gecko’s speech in Oliver Stone’s high finance 1987 thriller Wall Street. 

Taking a step back in time, Icahn: The Restless Billionaire rewinds to Carl’s childhood in Queens, managing to come top in class at some rather rough schools. While his parents bragged about his achievements in public, Carl was berated at home and had a tough childhood. Testament to this was his father’s decision to cover his Princeton university tuition fees but not his board and lodging. Possibly a blessing in disguise that made the self-driven man who he is today, this prompted him to get a job and hone his poker skills. Picking up a few books on the card game and mastering a few aspects of poker while working as a cabana boy, this street smart education prepared him for boardroom power dynamics. 

Icahn’s pluck is legendary, having had a knack for corporate combat and been involved in many classic rivalries. Taking board members to task, while instilling innovation and productivity to outmuscle competitors, the billionaire developed a sixth sense for knowing which companies could unleash their full potential under his guiding influence. Having been integrally involved with corporates such as Texaco, eBay, Herbalife and Netflix to name a few, Icahn: The Restless Billionaire unpacks several high profile case studies over the years with photos, footage and industry pundits weighing in to illustrate each chapter. Described as a corporate raider on more than one occasion, this is far from a puff piece but does paint Icahn in a positive light. 

Sharing intimate moments, fond memories and recalling some of his biggest moments through a series of candid interviews with Bruce David Klein, the investor opens up about his life’s story without pulling punches. As honest as he is in his podcast series with his daughter, Icahn enjoys his lifestyle and perch but says he made money because the system is bad, not because he’s a genius. Touching on his marriage to Gail Golden-Icahn, there’s not a great deal of detail on his family life, shifting the focus to his biography and business dealings. 

Icahn: The Restless Billionaire delves into the investor’s biggest hits, giving viewers a fair impression of the character, his motivations and contradictions without harking on the on-the-ground fallout from some of his sweeping changes. An influential figure and real-life Logan Roy, who has drawn attention to the very wealth gap he admonishes, this slick documentary remains entertaining and serves as a valuable lesson to future billionaires and captains of industry.