Before he transformed the skylines of Las Vegas and Macau or became a decisive donor to US presidents and Israeli prime ministers, Sheldon Adelson estimated he had done 50 different jobs.
Born in 1933, he was 12 when he borrowed $200 from his uncle to buy the right to hawk newspapers on Boston’s busiest street corners. By 16, he was selling sweet vending machines. After two years in the US army, he became a court stenographer, supplied soap to hotels and sold spray for defrosting car windscreens.
It was not until he was 32 and working as a mortgage broker that Adelson, who died on Monday aged 87, made his first $1m. He came close to bankruptcy soon after, having invested borrowed money in the stock market before the 1969 crash.
Within two years, however, he had bounced back, buying a bankrupt publishing company which owned a computer industry trade magazine.
Adelson’s realisation that the nascent industry had no trade show led him to launch the Computer Dealers Exposition in 1979. The first Comdex brought just 4,000 people to the MGM Grand in Las Vegas, but the personal computer revolution transformed the industry and by 1995 it was drawing crowds of 200,000.
That year he and his partners sold Comdex for $800m to Masayoshi Son’s SoftBank, giving Adelson the funds to embark on the venture that made him a billionaire.
He had bought the Las Vegas Sands from financier Kirk Kerkorian in 1989. His main interest was to build the country’s largest convention centre on the site. Sin City, he realised, could bring in suited conference-goers from Monday to Friday to complement the gamblers who crowded in on weekends. But an old Rat Pack haunt was not a sufficient draw, so he demolished the 17-storey building in 1996.
In its place he built the Venetian, a $1.8bn complex with a replica of the Bridge of Sighs, gondoliers crooning to the tourists they propelled along its desert canals and a fax machine in every room.
It made him a pioneer of the integrated resort model which now dominates the Las Vegas Strip. Its success convinced authorities in Macau to grant him a lucrative gaming licence when Stanley Ho’s gambling monopoly in the former Portuguese colony ended in 2002.
A history of organised crime hung over Las Vegas and Macau, but Adelson demanded “a certain moral behaviour” from employees, said Mike Leven, a former Las Vegas Sands president. “The gaming business has some ugly moments to it but Sheldon had principles. He was against prostitution and things like that.”
His attraction to casinos was underpinned by the belief in how profitable they could be when paired with conventions. And when Adelson had a strong belief, Mr Leven said, “he never varied from it”.
Over the past 20 years, he put more and more money behind two beliefs that came to define his public identity: the US Republican party and Israel.
The son of a Lithuanian Jewish cab driver and a Welsh seamstress, Adelson grew up sharing a tenement bedroom with his immigrant parents and three siblings.
Republicans had not even bothered to campaign in their poor Boston neighbourhood, but as Adelson’s wealth grew and he fought with culinary workers looking to unionise at the Venetian, his politics shifted to the right.
It was not “because I didn’t want to pay taxes or because of some other conservative caricature”, he wrote in 2012. It was that the Democrats failed to appreciate entrepreneurs and harboured “a visceral anti-Israel movement”.
Adelson backed his rhetoric with his estimated $35bn fortune. With his second wife Miriam, he contributed $82m to Republicans in 2016 and a record $218m in 2020.
The money earned him the friendship of presidents from George W Bush to Donald Trump, who he endorsed in 2016 as “a CEO success story that exemplifies the American spirit of determination, commitment to cause and business stewardship”.
Adelson’s influence was such that Barack Obama once called him to try to persuade Republicans over a budget sequestration battle, Mr Leven said. Adelson agreed to help, telling the then president: “I’m a Republican, but I’m first an American.”
His donations also made him hugely influential in US policy towards Israel. Adelson strongly opposed to a two-state solution and underwrote visits to Israel for scores of US politicians. He also funded a newspaper which staunchly supported Benjamin Netanyahu, the rightwing Israeli prime minister.
Adelson’s Zionist father had died before managing to visit Israel, so he wore his father’s shoes on his first visit.
Adelson attributed his philanthropy to his father keeping loose change for those in greater need than they were. Colleagues noted that when the Covid-19 pandemic shuttered casino floors, Adelson kept staff on full pay.
A litigious executive, he was once sued by two sons over a family stock deal. The judge concluded that Adelson “although perhaps lacking paternal kindliness and, indeed, cordiality generally, did not mislead, cheat or defraud [the] plaintiffs”.
Mr Leven said he was a controversial and “bigger than life character” for whom some struggled to work. “If he wanted to get something done in his particular way, you likely could not convince him to do otherwise.”