“I lost more money than anyone in capitalist history,” Ted Turner once said

(SeaPRwire) –   Ted Turner, who died this Wednesday at 87, never approached life with half-measures. In October 2006, I had the privilege of attending the opening of his Ted’s Montana Grill restaurant in midtown Manhattan. The invitation came as a “plus-one” from my close friend and fellow writer Pattie Sellers, who had profiled Turner for the magazine. (Pattie was a pioneering journalist known for founding the magazine’s influential “Most Powerful Women in Business” list and its renowned annual conference by that name.) The restaurant was conveniently located just one elevator ride from our offices on the 16th floor of the Time & Life Building, nestled in the art-deco lobby on the ground floor. Stepping into the venue felt like entering an 18th-century saloon fantasy, complete with an array of bison dishes—from pot roast to short ribs to steak frites. Turner owned one of the world’s largest bison herds and promoted bison meat as a healthier and more flavorful alternative to beef. His restaurants proudly offered a slice of “Big Sky sustainability,” notably ditching plastic straws, even amid Manhattan’s towering skyline.

When we arrived, Turner was the only guest in the dining room. He had played a pivotal role in building the Time Warner media empire where I worked (I belonged to one of its largest divisions, magazine publisher Time, Inc.), and I often wondered about the circumstances behind his sudden and bitter departure five years earlier. To summarize: Turner had sold Turner Broadcasting—owner of CNN, TBS, TNT, and the Cartoon Network—to Time Warner in 1996, receiving approximately $7.5 billion in stock from the acquiring company. However, in 2001, after Time Warner merged with AOL, CEO Jerry Levin effectively fired Turner by stripping him of all executive authority. What puzzled me was this: when Turner sold his creation to Time Warner, he amassed around 11% of its shares. Yet, to secure his massive payout, this restless entrepreneur reluctantly agreed to strict limitations on his influence. The deal included a so-called “standstill agreement” that barred Turner from launching hostile actions against the company, restricted him from buying additional stock, and essentially forced the outspoken maverick to support the Levin leadership on major decisions. The restrictions were so severe that Turner even publicly endorsed the controversial AOL merger.

Before the AOL acquisition, Turner served as Vice Chairman and oversaw his former networks. But Ted Turner never wanted to be a “Vice” anything. His ambition posed a significant threat to Levin. After several years, Turner could have likely exited his standstill agreement by resigning from the board and then pushing to oust Levin and assume the CEO role himself. After all, once free, he would wield immense power as Time Warner’s largest shareholder, holding over 10% of its stock.

The AOL transaction orchestrated by Levin, however, effectively neutralized Turner. It issued a flood of new shares, which cut his ownership stake in the combined entity by more than half, down to roughly 4%.

Besides Pattie and myself, the only other person to arrive within the first hour was actor Timothy Hutton, a friend of Ted’s. After chatting briefly, I seized the opportunity to ask Turner whether the strategic maneuvering I suspected had actually led to his dismissal: “Do you believe Jerry Levin structured the AOL deal, at least partially, to dilute your ownership and prevent you from using your substantial shareholder position to replace him as CEO?”

In a slow, measured tone, Ted Turner replied, “I don’t know if that was the main reason, but I do know it was on his mind.”

Turner seemed to believe that Levin saw the deal as a double win: securing a hefty premium from AOL for Time Warner shares, paving the way for a powerful new dot-com-media giant that would drive up the stock price—and simultaneously eliminate his most formidable rival.

In reality, shares of the newly formed AOL Time Warner plummeted almost immediately after the merger was announced. Enraged by both his ouster and the unraveling of the deal, Turner sold nearly all of his Time Warner stock in 2003, after the shares had dropped nearly 80%. He received about $3 billion for a stake that, in 1999 before the AOL merger, had been worth approximately $11 billion.

At the New York debut of Montana Grill that evening, Turner made another bold declaration: “I lost more money than anyone in the history of capitalism!” he told me. With characteristic audacity, Ted Turner wanted the world to understand that he always thought big—whether pursuing the America’s Cup on the open seas, revolutionizing journalism by launching the first 24-hour news network at CNN, or, no doubt, aiming to lead the world’s largest media conglomerate at Time Warner. Part of his irresistible charm was his unapologetic openness about losing big; he made it clear that, on rare occasions, he lost more than anyone else.