Herbert J. Siegel, Investor in Major Media Deals, Dies at 95

Herbert J. Siegel, a maverick investor who became a billionaire entertainment-industry mogul most notable for finally enabling the merger of Warner Communications and Time Inc. in 1989 and for selling 10 television stations to Rupert Murdoch’s News Corporation in 2000, died on Saturday at his home in Manhattan. He was 95.

His wife, Jeanne, said the cause was heart failure.

Mr. Siegel, the gregarious son of an immigrant garment manufacturer, combined his boyhood passions — deal-making and an infatuation with the film industry — to reap massive profits.

The humorist Art Buchwald once said that Mr. Siegel deserved an Academy Award for having earned the most money in Hollywood without ever making a movie.

Mr. Siegel got started young; he was still in college when, flush with a trust fund from his father, he sought to purchase a 20 percent stake in the Philadelphia Eagles of the National Football League for $60,000. His bid was unsuccessful, so instead he bought an interest in a company that packaged television programs and that was partly owned by his father-in-law, an organizer of the Columbia Broadcasting System.

After buying a brewery, a car-wax company and a jukebox manufacturer, he further insinuated himself into the entertainment business in 1962 by buying General Artists Corporation, a talent agency that represented, among others, Pat Boone, Perry Como and Jackie Gleason.

In 1965, after building a base at the Baldwin-Montrose Chemical Company, he netted $2.5 million from a failed bid for Paramount Pictures, then acquired the boat maker Chris-Craft Industries, where he served as chairman. His goal was to buy undervalued companies, funnel their earnings to Chris-Craft’s income statement and sell these investments for a capital gain.

“At 28, I was the youngest chairman of a company on the American Stock Exchange,” he told The New York Times in 1984.

He sold off Chris-Craft’s boat-making business and charmed Wall Street, despite losses at the company’s chemical division, the largest manufacturer of the insecticide DDT, and its television division.

He lost an eight-year bid to acquire Piper Aircraft, but in 1980 he sold his stake in 20th Century Fox, which he had begun accumulating two years earlier, for $74 million, collecting a profit of more than $800 million once Chris Craft Industries settled an acrimonious dispute that enabled Warner Communications to merge with Time Inc.

He had sought to buy Warner in 1968, then stepped in as the movie mogul Steven J. Ross’s white knight in the early 1980s, investing in a 21 percent stake in the company to fend off a takeover by Mr. Murdoch.

But their partnership soured after Mr. Siegel became vexed by Warner’s extravagant corporate culture and invoked an earlier agreement between Warner and Chris-Craft that delayed the Time-Warner merger until 1989. Chris-Craft’s stock soared as a result of the deal, and the company collected about $1 billion.

“We are delighted,” Mr. Ross and Mr. Siegel said in a statement, “that despite our earlier differences, the relationship between Warner and Chris-Craft is ending on a constructive and amicable basis.”

In 2000, Mr. Siegel reaped a windfall from the sale of 10 television stations to Mr. Murdoch’s News Corp. for $5.3 billion in cash and stock — a blockbuster deal that government filings estimated generated more than $1 billion for Mr. Siegel, although his family said he actually netted around half that amount. The sale provided News Corp. with valuable TV outlets in New York, Los Angeles and San Francisco.

“The name of the game is how well the shareholders are doing,” Mr. Siegel told The Times. “Are they richer because they made an investment?” He continued, “They want to make more money through capital gain, and that’s my responsibility.”

Mr. Siegel was not a hands-on manager. He conducted business by keeping one eye fixed on the Quotron stock-price monitor beside his desk and an ear to the phone while his lawyers were embroiled in hostile takeovers.

“Herb’s not the kind of guy who’s going to get grease under his nails,” J. Ira Harris, a former executive managing director of Salomon Brothers who was involved in Mr. Siegel’s negotiations with 20th Century Fox, said in 1984. “He’s a phenomenal asset manager rather than a business manager.”

Herbert Jay Siegel was born on May 7, 1928, in Philadelphia to Jacob Siegel, an overcoat manufacturer who had immigrated from Romania, and Frieda (Stern) Siegel, a musician and homemaker.

He graduated from Blair Academy in Blairstown, N.J., and then, in 1950, from Lehigh University in Bethlehem, Pa., with a bachelor’s degree in journalism.

That same year he married Ann Levy, whose father, Isaac D. Levy, had been an organizer of CBS. She died in 2005.

In 2007 he married Jeanne Sorenson. In addition to her, his survivors include two sons from his first marriage, John and William, and two grandchildren.

While Mr. Siegel was considered a generous philanthropist and was hardly miserly in his personal spending (Frank Sinatra sang at his first wedding; Tony Bennett sang at his second), he was taught the value of hard-earned cash early in life. One of his first acquisitions was a sentimental one: the overcoat company started by his father, who had come to America with the equivalent of $5 in his pocket.

“He insisted I pay him with a certified check and would take no stock,” Mr. Siegel said.