When America Online bought Time Warner in 2000, it was not only the largest corporate merger in history, but also a much-touted marriage of New Media and Old Media. Questions, however, began on the day the merger was announced by Steve Case of AOL and Jerry Levin of Time Warner. The stock price started a long decline, and the Federal Trade Commission subjected the merger to intense scrutiny. More than a year later regulatory agencies gave their approval, but AOL Time Warner’s troubles were far from over. A clash of cultures prevented the company from fulfilling expectations and AOL’s business slowed and then stalled. Just two years later, once-triumphant AOL is under investigation by both the SEC and the Justice Department. The company reported the largest loss in corporate history - USD100 billion - in 2002, and four of the top AOL and Time Warner executives present at the announcement of the merger - Case, Levin, Bob Pittman, and Ted Turner - resigned. How did the deal of the century become such an epic disaster?