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At age 32, after his father's death, he took over the family businesses and even made successes out of some that had been failing. He bought other print media as well as radio stations and television stations, successfully managing them as well.
His biggest success was the creation of TV Guide in 1952, which he started against the advice of his financial advisors. He also created and made fortunes from the Daily Racing Form and Seventeen magazine.
While he ran his publishing empire as a business, he was not afraid to use it for his own ends, both good and bad. One of hit publications, the Inquirer, was influential in ridding Philadelphia of its corrupt city government in 1949. It also attacked Senator Joseph McCarthy in the 1950s when most other publications feared McCarthy. It campaigned for the Marshall Plan after World War II. He also made many enemies: activist Ralph Nader, actress Zsa Zsa Gabor, boxer Sonny Liston, and many politicians became "non-existent" in his newspapers. Their names were never mentioned, and they were even air-brushed out of group photos. He eventually sold the Inquirer and the Philadelphia Daily News to Knight Newspapers for $55 million in 1970.
His first marriage, to Veronica Dunkelman, failed in 1949 after 11 years. His only son, Roger, committed suicide in 1962. Harvard University, where Roger was a student at the time, now has a Roger Annenberg hall in his honor. His marriage to his second wife, Leonore "Lee" Rosentiel, was, by all accounts, a lasting and fulfilling relationship. Lee was a niece of the late Harry Cohn, founder and successful mogul of Columbia Pictures.
Annenberg led a lavish lifestyle, enjoying his riches. His winter estate "Sunnylands" in Rancho Mirage near Palm Springs hosted gatherings with such people as Ronald Reagan, Frank Sinatra, Bob Hope, Bing Crosby and Charles, Prince of Wales. It was Annenberg who introduced Reagan to Margaret Thatcher, and the Reagans often celebrated New Year's Eve with the Annenbergs.
Even while an active businessman, he had an interest in public service. Richard Nixon appointed him ambassador to the Court of St. James's in 1969, and he became quite popular in Britain, eventually being knighted. His wife Lee was named by President Ronald Reagan as the State Department's chief of protocol.
After the sale of the Philadelphia papers, he established the Annenberg School for Communication at the University of Pennsylvania, which has become the premier school for communication in the United States. He also endowed another school for communication at the University of Southern California. He became a champion of public television, gaining many awards, including the Presidential Medal of Freedom from Reagan and the Linus Pauling Medal for Humanitarianism.
In 1989 he created the Annenberg Foundation, then, in 1993 he created the Annenberg Challenge, a $500 million, five-year reform effort, and the largest single gift ever made to American public education.
In 1998 he sold TV Guide, Seventeen, and a few other publications to Australian publishing magnate Rupert Murdoch for $3 billion, announcing that he would devote the rest of his life to philanthropy. The Annenberg Foundation gave away billions, mostly to educational institutions. "Education...", he once said, "holds civilization together." Many school buildings, libraries, theaters, hospitals, and museums all over the United States now bear Annenberg's name. It is estimated that he gave over $2 billion in his lifetime. His collection of French impressionist art is valued at approximately $1 billion, and has been donated to the Metropolitan Museum of Art in New York City.
Annenberg died at his home in Wynnewood, Pennsylvania in October 2002, at the age of 94. He was survived by his wife Lee, daughter Wallis, and two sisters, Haupt and Evelyn Hall. Including those by his wife's daughters from his first marriage (Diane Deshong and Elizabeth Kabler), he left behind seven grandchildren and six great-grandchildren.