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 August 12, 2023 at his home in Manhattan. He was 95. His wife, Jeanne, said the cause was heart failure. 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. 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 at age 28. 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. 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. 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. Frank Sinatra sang at his first wedding; Tony Bennett sang at his second.