The Improbable Life Of Sheldon Adelson, Republican Kingmaker And Casino Billionaire

Sheldon Adelson only bet big. Whether he was wagering on a new casino location, a controversial business model, or a conservative political candidate—he’d make his pick and throw hundreds of millions of dollars, often billions, behind it. More than anyone, he bet on himself— ignoring critics, rivals and often his executives as he laid his fortune on the line to back long-odds bets—damn the consequences. “Some people call me an optimist,” Adelson told Forbes in 2012. “The fact is that my appetite for risk was far greater than other people, and my courage in my own conviction was unshakable.”

His conviction could bring Las Vegas Sands on the brink (during the 2008 credit crisis, his refusal to refinance debt and or pause construction on Macao casinos nearly destroyed the company). But Adelson’s bets eventually paid off.

With his business winnings Adelson, who died January 11 from complications related to the treatment of non-Hodgkin’s Lymphoma, made himself a power player in casinos, hotels, media and politics. At the time of death, Forbes estimates he had a net worth $35 billion, making him the 19th richest person in the world. The fortune gave Adelson outsized influence that stretched beyond his walled kingdom on the Las Vegas strip to entertainment empires in Macau and Singapore, newspapers in Israel and Nevada, and most recently in halls of Washington D.C where he played the role of Republican kingmaker whose nearly-limitless donations could fuel or foil political careers. 

Slums To Slots

Adelson’s fate as a conservative kingpin was far from preordained. He grew up in Boston’s then-rough Dorchester neighborhood. His parents were Jewish immigrants, his father from Lithuania, his mother from Wales. The family lived in a one bedroom walkup where the parents got the mattress and the kids slept on the floor. The streets taught Adelson, who never shied away from a public spat, how to fight. “We had to go to school with at least four kids,” Adelson told Forbes about the anti-Semitism in the neighborhood when his was young. “The Irish kids came out of the bushes and tenements with rubber hoses and chains and brass knuckles.”

He took refuge in business, selling papers at age twelve and later buying vending machines to place in busy gas stations where taxi drivers (his dad drove a cab) fueled up 24-hours a day. After high school he joined the Army, sold advertising in financial publications and later began brokering deals between small banks and start-up businesses in need of funding. Soon he was organizing syndicates of suburban banks to back commercial real estate and later jumped into the burgeoning condo markets. As he told Forbes: “it was back in the 1970s when most people thought a condominium was a form of birth control.” 

Next came hotels and then Interface, his trade show company that would eventually start Comdex—the essential tech summit at the dawn of the 1980s computer revolution. Based in Las Vegas, Comdex attracted more than 100,000 guests a year. In 1989, he had enough revenue to go from renter to owner, buying the Sands casino for $129 million. 

In 1995 he sold the Comdex conference to Softbank for $890 million and plowed the proceeds into the Venetian—a $1.5 billion Las Vegas casino that helped shape the future of Sin City with suite-only rooms, high-end retailers and restaurants, and massive event spaces.

The Global Casino Kingpin

The Venetian strategy was a success, and Adelson scouted the globe for other cities to repeat the recipe. First came Macao—a once seedy port town a few hours from Hong Kong—which was quickly transforming into China’s Vegas Strip. The Sands Macao—a barebones casino with a small hotel attached—arrived in 2004. The much larger and opulent Venetian Macao opened in 2007. That same year, Adelson took on $10 billion in debt to fund an all-out building boom which now included a $1.9 billion expansion in Las Vegas, a massive $12 billion project in Macao’s Cotai Strip and the $5.5 billion Marina Bay Sands in Singapore. Adelson had a hot hand. Then the 2008 credit crisis hit. 

For Adelson, the recession delivered twin blows. Casino and hotel revenue evaporated as business conventions and tourism spending vanished overnight. Meanwhile banks, facing their own financing disasters and fighting to stay alive, began calling in their loans. 

Shares of Las Vegas Sands fell 50%, then 80%. Adelson’s finance team scrambled to refinance debt and sell new bonds, but the boss rejected each offer, betting (as always) that the markets would recover and that he could give up less equity if he waited.

The move seemed fatal—Lehman Brothers soon blew up, throwing the credit markets into a full panic. Shares of Las Vegas Sands dropped  99% down from their peak. The company teetered on the brink of bankruptcy. To keep the company afloat, he committed his remaining $3 billion to keep the Sands alive. In one of the boldest double-downs in business history, he invested $1 billion of his own cash to prop up the company. 

The investment bought the company the time it needed. The economy recovered. Travel returned, and the construction that he refused to slow created a series of casinos in Macao and Singapore that proved to be goldmines. Over the next four years, Sands shares (of which Adelson owned 50%) surged 3,700% taking Adelson’s fortune from $3 billion to $27 billion. “I’m too old to be a kid,” Adelson told Forbes in 2012. “So you can call me the comeback adolescent.”

Steve Wynn, the founder of Wynn Resorts, a longtime rival and eventual close friend to Adelson, says Adelson’s bet on Cotai was one of the greatest money-making schemes ever pulled off in the gambling world. 

“Sheldon played it so good. Think about the guts and vision required to build Cotai. I don’t know how you play a better hand,” says Wynn. “He was my favorite competitor ever—Adelson will be hard to replace.”

No American, not even Mark Zuckerberg had made more money during the first Obama administration. Soon, Adelson would spend his recovered fortune trying to get Obama and the democrats out of power. 

Republican Power Player

In 2012, Las Vegas Sands started issuing quarterly dividends to shareholders for the first time. Over eight years, like clockwork, Adelson collected between $90 million and $260 million in dividends every quarter—all favorably taxed at 15%. The chairman and chief executive even had a well-known catchphrase he liked to say during his company’s earnings calls: “Yay, dividends!”

Republican candidates were just as excited. Adelson and his wife Miriam used the hefty payouts to power mega-political donations to Republicans. Always known to political insiders, Adelson’s political ambitions and influence became national headlines when the casino billionaire donated $11 million to resurrect former House Speaker Newt Gingrich’s presidential campaign. 

When pundits and political opponents accused Adelson of trying to buy the presidency, as usual he increased his wager. “Those people are either jealous or professional critics,” Adelson told Forbes in 2012. “They like to trash other people. It’s unfair that I’ve been treated unfairly—but it doesn’t stop me. I might give $10 million or $100 million to Gingrich.”

He and wife Miriam would eventually give more than $90 million to Mitt Romney and other Republican candidates in 2012. The donations continued in midterm races and again spiked in the 2016 election cycle where the Adelson’s spent $82 million. The couple were not early supporters of Donald Trump, but they eventually donated $20 million toward the pro-Trump super-PAC Future45. For the 2018 midterms, the Adelsons disclosed spending $123 million on Republicans, and conservative causes.

The historic 2020 election drew historic donations from Adelson. In total, they spent $180 million, including $75 million to a super-PAC funding ads opposing Joe Biden and $1.2 million to a joint-fundraising committee backing Trump. At the time of his death, the couple disclosed over $500 million in donations over Adelson’s lifetime, mostly to Republicans, hawkish Israel policy, and conservative causes, according to Federal Election Commission filings. 

The Final Hand

For Adelson and Las Vegas Sands shareholders, 2020 started on a high note. In early January shares of Sands hit a one year high with a market cap topping $56 billion. Soon, like the rest of the economy, the Covid-19 pandemic brought his gaming and resort empire to a grinding halt for months. Las Vegas Sands’ stock crashed 54% in March from its 52-week high. The next month Sands suspended its dividend program.

In October, Sands reported that its third quarter revenues were down 82% from a year ago. In Macao, the most important market for the company, sales were down 92%.

But, Las Vegas Sands has been able to weather the downturn. Once nearly crushed under its own debt during the 2008 recession, today it boasts one of the strongest balance sheets in the industry and has enough cash to operate without revenue for more than 18 months. Betting on brighter days ahead, Sands continues to invest billions of dollars in its mega-properties in Macao and Singapore.

Adelson’s global wager seems to again be paying off. A Deutsche Bank research note published in October, reaffirmed a buy rating for Las Vegas Sands, noting that Covid-19 and the presidential election could make business tough for casino operators with assets only in the U.S. But Sands is in a good position as 90 percent of its profits come from its Asian properties. 

In fact, before his death, Adelson looked to be cashing in the chips of his American business. In October, news broke that the company is exploring a sale of its iconic Vegas assets— the Venetian, the Palazzo, and the Sands Expo Convention Center. The properties could go for $6 billion. 

There were signs too that he was closing out his Trump wager. In November the Las Review-Journal, which Adelson bought in 2015, published an editorial calling for Trump to concede his loss to President-elect Joe Biden and laid into Trump’s false claims of a “rigged” election.

The Review-Journal endorsed Trump in 2016 and 2020, and although former Review-Journal employees said that Adelson was hands-off when it came to the newspaper’s content, at times the Adelsons’ political views, and even their own words, found their way onto the pages of their paper. 

Editors at the paper refused to speak on whether Adelson approved the editorial or not. But what’s most interesting about the piece is not whether Adelson approved, but what it represents—one of the biggest Republican donors in history indirectly signaled to Trump that he lost and it’s time to leave.

Still on January 12, President Trump, who has remained mostly silent and hidden since the riot on Congress, briefly emerged to release a press statement on his benefactor’s death. “Sheldon lived the true American dream. His ingenuity, genius, and creativity earned him immense wealth, but his character and philanthropic generosity his great name.” 

Whether or not Adelson formally cut ties with Trump, it’s hard to miss the irony that one of the largest and most influential players in Republican politics died during the tumultuous and chaotic waning days of Trump’s presidency.

While Adelson has passed, his influence in politics and gambling will remain—his wife Miriam and his family now steer a fortune north of $30 billion. 

Michela Tindera contributed reporting to this story.