My piece on Sheldon Adelson for POLITICO

Sheldon Adelson, the most successful gambling entrepreneur in history, is terrified.

If web gaming is legalized, the self-made multibillionaire and mega-donor insists, big-name Silicon Valley companies will invest heavily in the business, eventually coming to dominate the market with their superior technology and global reach. States will smell money and levy taxes. And then it will happen: the apocalypse, sayeth the Cassandra of gaming soothsayers, who is putting his fortune where his crystal ball is.

“Somebody like Google or Facebook, they’ve got a billion customers hitting them every day,” marveled Adelson, who chairs Las Vegas Sands, which owns the Venetian and the Palazzo on the Las Vegas Strip, in a lengthy recent interview. “They’ll come in there, they’ll squash the other guys like … you squash the little ant running across the table or the floor and that’s going to be the end of all of it.”

Is this man bluffing?

“I’ve been an entrepreneur for 68 years,” the 80-year-old casino mogul told me as we sat in a conference room at his offices at the Venetian, a cavernous space with one entire wall festooned with magazine covers with his picture. He was surrounded the entire 75 minutes during this rare sitdown by two aides and his wife, Miriam, a success in her own right as a doctor who specializes in addiction. “I’ve never failed yet. And I’m telling you, the one characteristic of a successful entrepreneur is to have courage and belief in your own convictions.”

If there’s one thing Adelson believes in, it is himself. The octogenarian who parlayed a computer trade show into a billion dollars, sold it in 1995 and bought the place where the Rat Pack hung out, then erected the Venetian where the Sands once stood, knows not of equivocation. And if you listen to him talk about the dangers of web gaming, he does not vacillate, he does not doubt, he does not flinch.

Adelson has said he will spend whatever it takes— he is worth an estimated $37 billion and his earnings dwarf those of all other gaming companies—embarking last fall on what a rival calls a “jihad” to stop Internet wagering and threatening to use his ample political muscle as the country’s largest GOP donor to stop what many think is unstoppable. Now, he’s funded an anti-web gaming coalition, tapped former politicians as mouthpieces and vowed to go state by state to end the scourge.

He cannot be ignored. But despite his undeniable successes in the convention business and in the hard-knocks world of casinos, Adelson has mostly failed at the one business he needs to excel in to achieve his goals now: politics. From seeking to control local elected boards and defang unions to bankrolling pro-Israel groups opposed to Middle East peace talks to spending at least $100 million in 2012 to oust President Barack Obama, Adelson has given much and reaped little.




Read more.