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Sheldon Adelson / Photo courtesy of East Coast Gambler under Creative Commons

We live, more than ever, in a world of caricatures.

Perceptions are fueled by partisan animus, economic dislocation and increasing alienation. People are good or evil. You either hate or love. Nuances disappear. Simplicity substitutes for clarity.

Sheldon Adelson embodied this more than almost anyone, beloved by those who admired his acts of boundless generosity, unmatched entrepreneurship and visionary accomplishments and reviled by those who despised his Republican donations, anti-union crusades and occasional vindictiveness.

There were very few people who were agnostic about Adelson, who died last week at 87. But like so many human beings, especially remarkably successful ones, he was a complex man, just as likely to quietly help a wounded warrior as he was to try to bankrupt a journalist who displeased him, just as likely to donate significant sums of his fortune to Israel-related charities as he was to obsess over a dispute with the Las Vegas Convention and Visitors Authority for decades, just as likely continue to pay his employees throughout a pandemic as he was to muse about nuking Iran.

Much has already been written about Adelson, some of it hagiographic, some of it hateful. He was as polarizing as almost any non-elected public figure alive.

While there were some notable praiseworthy columns, I do not think I have ever seen the level of disgusting savagery in the social media sewer that the announcement of his death occasioned. And yet I also think all of us would like the person closest to us to write as touching a remembrance upon our deaths as Miriam Adelson did for her husband.

But I come not to bury or simply praise Adelson, knowing full well that what many felt was evil about him will live on and that much of the good he unquestionably did will be interred in Jerusalem, where he was laid to rest a few days ago and where he was able to after so many years persuade a president to move the Israeli embassy.

Adelson’s impact on the gaming industry and state and national politics (not to mention that of Israel’s) cannot be underestimated. He revolutionized the industry’s attitude toward conventions and proved the doubters wrong with his all-suite approach and investment in Macau. He more than anyone else was responsible for bringing the Raiders to Las Vegas — an idea he conceived and then devoted all of his company’s resources to pushing a (sweetheart and awful) financial deal through the Legislature for what would become Allegiant Stadium.

Adelson is a seminal figure in the history of Las Vegas, deserving of a place in the pantheon that began with Bugsy Siegel and includes Howard Hughes, Kirk Kerkorian and Steve Wynn. Indeed, in many ways, Adelson was the anti-Wynn.

Unlike the undeniably charismatic, brilliantly articulate and preternaturally extroverted ex-chairman of Wynn Resorts, who hobnobbed with celebrities and loved being in his own ads, the more private Adelson was driven by his desire to succeed and prosper, ever the poor kid from Dorchester, ever the outsider.

The Mirage and the Bellagio were spectacular, yes, but The Venetian and the Palazzo were, too, in their own way.

“He was not afraid to go all-in and take his position based upon his opinion without looking over his shoulder or second-guessing himself,” Wynn said after Adelson’s death in an almost perfect coda for the Las Vegas Sands chairman’s life, a quote that is at once laudatory and somehow not. Adelson was indeed driven, was hard to dissuade when he had an idee fixe about politics or business. One of those was that Macau was an untapped gold mine for the industry, which occasioned much derision inside the industry but ultimately resulted in Wynn coming to Adelson for tips on entering the market.

“Steve liked to share his vision, and so did Sheldon in a much more practical way, with far less color and adjectives,” said Andy Abboud, who for 23 years was the chairman’s political right hand. “He had a very practical business sense, would walk through the financial modeling of integrated resorts, why you have so many square feet of convention space, the mechanics of how you make money.”

Or as someone else who knew him well told me: “He was a finisher. He did what he said he was going to do. He was not all talk; he was all do.”

My sense was that some people were jealous of Steve Wynn but some people just hated Sheldon Adelson. He was the incarnation of the billionaire trying to buy elections and politicians simply to make or save himself more money.

“Anybody who is high-profile and has been a disruptor as he has been – in philanthropy, in business and in politics – he is going to make enemies,” said Matt Brooks, the executive director of the Republican Jewish Coalition that Adelson helped fund.

But those who really knew him said Adelson did not contribute hundreds of millions to politicians and PACs over the years because of his personal bottom line. For him, especially after he became wealthy, the money was just a way of keeping score – and by that metric, no one in the business he had chosen came close.

Adelson’s politics were not as easy to pinpoint as his pre- and post-mortem cartoonists tried to do. Yes, he was a zealous supporter of Israel, an unabashed Zionist and a fiscal conservative.

But he was also pro-choice, pro-gay marriage and pro-immigration reform. He strongly believed the GOP was wrong on immigration, his immigrant parents always on his mind.

Adelson also diverged from many in his party – including some bleating daily in Nevada – about the pandemic and the government’s response.

“He never was going to diminish how horrific the pandemic would be, and he never had a problem with any of the measures that came down (from the governor),” Abboud told me. “The pandemic scared the daylights out of him.”

Adelson’s decision to continue to pay his employees – even after COVID lasted much longer than a month or two – was widely and justifiably lauded. Sure, he could afford to do it more than his counterparts, but he also spared his workers from untold hardships.

It’s hard to believe the man he helped elect, President Donald Trump, would have done the same. And while Adelson surely had little regard for Trump’s lack of substance, he also probably saw him as a winner and used him to pursue his political agenda. And Trump, for his part, if he respected anyone, it was someone who had (a lot) more money than he did.

By contrast, Adelson’s little-known backchannel relationship with the most powerful Nevadan ever to hold office – Democratic Sen. Harry Reid – was a testament to both Adelson’s practicality and his and Reid’s similar blunt styles. Reid knew that Adelson could marshal significant resources against him in campaigns, and Adelson knew that Reid had ascended to the pinnacle of capital power. It was a symbiosis that served both men.

That’s not to say there wasn’t a darker side to Adelson’s involvement in politics.

His effort to discredit former employee Shelley Berkley, by releasing internal company memos she wrote and going all out to beat her in a race for Congress, was ruthless and nasty. He once hired a quite-inept Las Vegas consultant to try to defeat three Democratic Clark County commissioners and was dubbed the “billionaire bully” in mail pieces. And his team essentially created the phenomenon known as Adam Laxalt out of whole cloth and ran one of the nastiest campaigns in recent history against Steve Sisolak in the 2018 governor’s race.

All of which goes to show that Adelson…often wasn’t very good at politics.

Berkley won that race, all three of his candidates for the Clark County Commission lost and, of course, Sisolak is now governor. And even when he had success, it was nothing to boast about. Adelson now has the unique distinction of having spent a fortune to help elect arguably the worst governor in the state’s history (Jim Gibbons) and arguably the worst president in the country’s history (Trump).

Adelson also spent an inordinate amount of time in what seemed like petty feuds, whether it was pitting one local temple against another or suing journalists near and far.  I’m sure Adelson thought he was wronged. But the lengths he went to, especially with The Indy’s John L. Smith, as the columnist detailed in a piece for The Daily Beast, were quite appalling and frightening.

Sometimes, it seemed, it wasn’t enough for Adelson to win. He sought to crush, maim, destroy. (His Javert-like pursuit of the convention authority and its leaders through a half-century after feeling he had been disrespected when he owned COMDEX fits this pattern, too.)

Emphasizing the duality of the man, Adelson’s many acts of generosity and kindness, some known and many unknown, show a much different side.

He gave tens of millions of dollars to groups such as Birthright Israel, which offers free trips to the country for young adults, and other organizations there. And he has long been a supporter of veterans, including his work with the Wounded Warriors Project.

“When we would do the Wounded Warriors, he would always go and chat with them at dinner,” Abboud recalled. “He would quietly do these incredibly generous things, help them financially, provide medical assistance and long-term care. No one ever knew about it.”

I was particularly struck by a Facebook post from Ed Bernstein, the well-known lawyer and onetime Democratic candidate for U.S. Senate, about his daughter, Dana, who died three years ago after a long battle with Crohn’s disease.

“There wasn’t a time when Dana would call him for a medical emergency that he didn’t respond immediately and offer his help,” Bernstein wrote. “He was always kind and loving to her and I will forever be grateful for that. His generosity and good deeds will be remembered by many.”

As for my relationship with Adelson, I knew and observed him for more than 30 years, from before he imploded The Sands to make way for The Venetian, after which I referred to him as Gondolier Numero Uno. (I was told he chuckled.) I did not know him well, but I interacted with him and his agents enough times to get more than a sense of the man.

We had cross words a few times, but I always found him to be a fascinating and refreshingly candid interview, whether he was on my TV show or in his office or if I ran into him at an event and managed to get by his security detail.

(One thing that has stuck with me is how protective Miriam was of her husband, whether it was her standing a few feet away from the camera when he was on the show or wandering into his office when I was interviewing him and occasionally admonishing him, “Say ‘off the record,’ Sheldon!”)

There was a mutual respect, but we were never friendly per se. Indeed, I always believed he was behind a threatened lawsuit against The Indy when we considered publishing a negative story about the Review-Journal and I suspected (and I was hardly alone) that he might have been behind the abrupt cancellation of my television show by craven public television overlords. But in both cases, I was Tessio talking to Tom Hagen; I knew it was only business.

Ironically, Adelson became the best fundraiser The Indy could have hoped for as his purchase of the RJ induced many a donor to help contribute to an alternative news source. I was – and remain – disturbed by his purchase of the newspaper. He also owns one in Israel, and it is known for having been a political billy club for Bibi Netanyahu.

Sure, other billionaires own newspapers. But no billionaire so enmeshed in the political and economic fabric of the state, and a small one at that. I thought it was dangerous, and his initial effort to keep his ownership a secret and the newspaper’s subsequent kowtowing to him only confirmed my fears.

Don’t get me wrong; I don’t believe he constantly hectored editors, and there were and are good reporters there impervious to such pressures.

But when you assemble an investigative team and its first project is to go after your bete noire (the convention authority) and Miriam is allowed front-page columns and mandatory-to-publish talking points are sent over on what to report about a trial involving the Sands and…well, you get the picture.

So, yes, I acknowledge it bothers me deeply, and I have pointed out when editors there, either pre-emptively or after a call from a Sands minion, bent to his will. All these last five years, though, Adelson never expressed any anger at what I was saying vis a vis the RJ, mostly because, I think, he didn’t care that much.

I’m not sure where the RJ goes now that he is gone, nor do I have much insight into the future of the empire he built — I’ll leave that to experts like Howard Stutz.

But, love him or hate him, Adelson’s passing is going to leave a huge vacuum in the worlds of politics and gaming. “A force of nature,” as one associate called him, and you always knew which way the wind was blowing with Adelson.

I often thought to myself during the last few years that rather than pressing forward into new markets or enmeshing himself in the political fray or getting into pointless scrapes that Adelson should just take his billions and go enjoy his remaining years. And you know what?

Maybe he did.

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