Nov. 19, 2010 -- Las Vegas is a place where many bet high but few come out on top ... and then there's Sheldon Adelson, who proves that old Vegas saying, "The house always wins."
The billionaire behind the Las Vegas Sands Corporation likes things big, including his checkbook.
"A friend of mine says, 'You're the tallest guy in the world,'" he said in an interview with "Nightline's" Cynthia McFadden. "I says, 'How do you figure that?' He said: 'When you stand on your wallet.'"
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Before the economy fell apart two years ago, Adelson's company was making an estimated $20 million per day from his hotels and casinos in Las Vegas and Macau.
His properties are huge. In Vegas, the Venetian and Palazzo complex, at 18.5 million square feet, is three times the size of the Pentagon and boasts the title of the largest hotel in the world. In Macau, he spent $2.4 billion on a 3,000-room resort.
Adelson has a reputation for being very tough, and he has a very tough background to match.
"In my mind, here's a kid who comes from the slums, me," Adelson said. "I came from a very poor family, there were six people, four children, and my parents, one bed in the room ... and my parents were poor.
"When they died in 1985, 11 days apart," he said, "they didn't have as much as $100 in the bank. Their whole life. They gave everything to their children. So I'm talking not from a white shoe background or from a privileged background. I'm talking [as] somebody who wore his skin down on his fingers trying to climb the ladder of success."
By 2007, he seemed to be minting money. With an estimated net worth of $40 billion, he was one of the richest men in the world and No. 3 on the Forbes magazine list of richest Americans, just behind Bill Gates and Warren Buffett.
His extravagance, he said, is airplanes. Together, he and his company own 14 aircraft.
It's "probably the largest private fleet in the world," Adelson said. "But we use the planes very wisely because we use the planes to bring players in. It gives us an advantage over others."
But the planes and the perks looked as if they might have been in jeopardy when the market crashed in 2008. His company's market value plummeted more than 90 percent, at one point losing as much as $1,000 per second.
Adelson: There's 'No Such Thing as Fear' to an Entrepreneur
Adelson didn't blink.
"So I lost $25 billion," he said. "I started out with zero."
"It certainly wasn't the most joyous moment of my life, but there was nothing that anybody could do," Adelson said. "You could look at the Dow Jones industrial average and see it swing 500 points or 1,000 points in a day and you say, 'This is incredible! What can anybody do to stop this?'"
Adelson said he takes "a very small portion" of the blame for what happened to his company.
"I was the guy that had to put the money in," he said.
To prevent the company from going under, Adelson and his family invested $1 billion into the Las Vegas Sands Corporation.
"$1 billion doesn't buy you what it used to," Adelson joked.
That $1 billion bailed out the cash-strapped company, but much of the senior management was fired. Adelson claims he never really broke a sweat during it at all.
There's "no such thing as fear -- not to an entrepreneur," he said. "Concern, yes. Fear, no."
Even in the depth of the financial crisis, Adelson never backed off from a planned multi-billion-dollar project in Singapore. The Marina Bay Sands Hotel is now open.
It's another massive structure, with three 55-story hotel towers joined together by a 40,000-square-foot sky park, 500-foot pool, two theaters holding 4,000 seats and 800,000 square feet of retail space. Adelson said the complex cost $5.6 billion to build.
"As I keep saying, who's counting," Adelson said, adding he had no doubt that the Marina Bay Sands would be a success.
He turned out to be right. In its first full quarter of operations, it generated a whopping $242 million in profits. His Las Vegas properties, unlike many on the strip, are thriving as well. For the third quarter of this year, they booked record profits of $645 million.
Adelson isn't quite back to his 2007 heyday, but he's working on it: He dropped to No. 26 on the Forbes list in 2009 and now stands at No. 13. Asked if he'd like to see himself back on top, he answers, "Why not?"
At 77, he shows no signs of slowing down. He and his second wife, Miriam, have been married for 19 years. Together, they have two sons, ages 11 and 13. Adelson has three other grown children.
Still a Cabbie's Son
For all his riches, Adelson is still the son of a Boston cabbie. His parents, he said, could never comprehend the scope of his wealth.
"When I was able to support them and have them live in a more luxurious way, my mother would still take the bus," he said. "I would say, 'Mother, let me send a limo,' and she would say, 'You can't teach an old dog new tricks.'"
But you can raise a son who grows up to have a fleet of planes.