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The original source of Adelson's wealth and current investments was the computer trade show COMDEX, which he and his partners developed for the computer industry; the first show was in 1979
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In 1988, Adelson and his partners purchased the Sands Hotel and Casino in Las Vegas, the former hangout of Frank Sinatra and the Rat Pack, in order to bring Las Vegas to a new source of business from the exhibition industry.
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The following year, Adelson and his partners constructed the Sands Expo and Convention Center, then the only privately owned and operated convention center in the US.
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In 1991, while honeymooning in Venice with his second wife, Miriam, Adelson found the inspiration for a mega-resort hotel. He razed the Sands and spent $1.5 billion to construct The Venetian, a Venice-themed resort hotel and casino.
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In 1995, Adelson and his partners sold the Interface Group Show Division, including the COMDEX shows, to SoftBank Corporation of Japan for $862 million; Adelson's share was over $500 million.
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In 2003, The Venetian added the 1,013-suite Venezia tower – giving the hotel 4,049 suites; 18 restaurants and a shopping mall with canals, gondolas and singing gondoliers.
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The one-million-square-foot Sands Macao became the People's Republic of China's first Las Vegas-style casino when it opened in May 2004. Adelson recovered his initial $265-million investment in one year and, because he owns 69% of the stock, he increased his wealth when he took the stock public in December 2004.
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In 2007, Adelson made an unsuccessful bid to purchase the Israeli newspaper Maariv. When this failed, he proceeded with parallel plans to publish a free daily newspaper to compete with Israeli, a newspaper he had co-founded in 2006 but had left. The first edition of the new newspaper, Israel HaYom, was published on July 30, 2007.
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In August 2007, Adelson opened the $2.4-billion Venetian Macau Resort Hotel on Cotai and announced that he planned to create a massive, concentrated resort area he called the Cotai Strip, after its Las Vegas counterpart.
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In the late 2000s, Adelson and the company decided to build a casino resort in Bethlehem, Pennsylvania. It is one of five stand-alone casinos that were awarded a slots license by the Pennsylvania Gaming Control Board in 2006. The casino opened May 22, 2009.
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In May 2006, Adelson's Las Vegas Sands was awarded a hotly contested license to construct a casino resort in Singapore's Marina Bay. The new casino, Marina Bay Sands, opened in 2010 at a rumored cost of $5.5 billion. It includes a shopping mall, convention center, and 2,500 luxury hotel rooms.