Like bettors at a Roulette wheel, Donald Trump’s campaign staff, advisors, and donors all gather around, wagering on the outcome of the volatile candidate’s bid to become the next president of the United States of America. But unlike the more familiar “horse racing” analogy used to describe political races, aka when a party places its bet in favor of a specific horse with an observable record of performance and said horse runs on a familiar and predetermined track, the roulette wheel is proving to be a more apt casino game in personifying Mr. Trump’s Presidential campaign. Even a casual observer can piece together that the only thing predictable about this candidate is his unpredictability.
Bearing this in mind, it makes sense that the one trait that might link together all of the key players in Donald Trump’s campaign, is an impulse to spin the roulette wheel – each player wagering a unique amount and hoping the ball stops on the number that would serve them best.
Let’s get familiar with a few key players:
Sheldon Adelson – Donor
Adelson, a casino mogul who has made billions of dollars heading up the Las Vegas Sands Corporation, would seem to have a natural affinity for the inner workings of a casino. Adelson has never been opaque about the policies that are important to him, and two of these issues remain firmly in his sights: the protection of Israel, and the protection of his business.
During the primaries, Adelson pledged to donate $100 million to Donald Trump’s campaign. But as the Republican convention loomed, Trump’s campaign made missteps – you know, just your everyday misstep, like tweeting an image that utilized anti-semitic imagery from another Twitter user who likes to post racist propaganda.
Needless to say, Adelson’s wager appeared to be stalled in a holding pattern at the time of the convention. Was he no longer so sure of his bet? Trump’s Jewish son-in-law, Jared Kushner, may have been able to convince him that Trump would honor his interests, but perhaps Trump’s policies could be too easily swayed by the rabid adoration he receives from those who harbour deeply rooted nationalist and anti-Zionist ideology?
Sheldon Adelson’s choice to stack his chips in Trump’s favor during the primaries likely had a great deal to do with the campaign assuring him that Trump would honor his opposition to the legalization of online gambling as well. A vocal and monetarily-influential opponent of the growing mainstream presence of online casinos and online poker in the United States, Adelson has funneled approximately $100 million dollars into Congressional races between the years of 2012 and 2014. He has also maintained a laser focus on influencing politicians to pass the Restoration of America’s Wire Act, which would prohibit online gambling, including fantasy sports betting – the latter of which Adelson is more closely tied to having become a recent NFL team owner.
Adelson’s pledge was also meant to inspire Trump to choose Newt Gingrich as his running mate, who has been very loyal to the causes that Adelson is passionate about. But it did not succeed. Instead, Trump went with the Christian conservative favorite, Mike Pence, whom would end up being a decent consolation prize for the billionaire casino magnate.
Mike Pence is pro-Israel and has an even stronger record of opposing online gambling. In 2003, Pence voted in favor of the Unlawful Internet Gambling Funding Prohibition Act, which made it illegal for financial institutions to process online gambling transactions. In 2006, he voted for the Internet Gambling Bill, which placed further restrictions and imposed a five-year prison sentence on anyone who violated those restrictions. Later that year, he then voted for the Unlawful Internet Gambling Enforcement Act, surely permanently cementing himself as an Adelson “Anti-Online Gambling” darling. Pence even wrote a letter in 2014 to his fellow lawmakers strongly urging them to vote in favor of the The Restoration of America’s Wire Act.
It would seem that the choice in Pence paid off, because as first reported by CNN in late September, Adelson stepped forward with a $45 Million investment to go toward Republican campaigns, $5 Million of which would be earmarked for Trump. The donation is the largest of the 2016 election cycle thus far. But then again, maybe it’s because Trump has Jewish grandchildren – something Trump himself loves to mention.
Jared Kushner – Campaign Advisor
Donald Trump’s son-in-law and husband to Ivanka burst onto the scene at the age of 23 when he had to step in and help run his father’s real estate business – his father being Charles Kushner, who was convicted of charges of tax evasion, illegal campaign donations and witness tampering in 2004. Two years later, Jared took a $10 million gamble in purchasing The New York Observer, a publication that once held cultural significance among New York’s elite society, but was losing money and suffering from the same atrophy experienced by many other papers. His bet began paying off five years later in 2011 when the The Observer finally began to turn a profit due to Kushner converting it into more of a ‘tabloid’ model with a stronger online presence. The cost of doing so was its respectability amongst the intelligentsia and social elite.
In 2007, Kushner pulled together $1.8 billion to purchase 666 5th Avenue, which now houses his offices. Two years later, he married Ivanka Trump, whom he was introduced to by Rupert Murdoch’s then wife, Wendi Deng.
But what exactly is Jared Kushner betting on in his father-in-law’s campaign to become President of the United States?
One possible answer is that Kushner is becoming so highly involved in Trump’s campaign to ensure he and his wife’s brands and businesses are able to survive relatively unscathed after all is said and done. A piece at Bloomberg Business Week calls it Kushner’s “Trump Card”. Managing the effects of a scandal caused by a father figure is certainly not uncharted territory for him; and colleagues and friends report that he is incredibly measured and well-mannered, which is a valuable political survival skill.
That said, what Jared Kushner may ultimately be hoping to win by entangling himself with the political prowess of his father-in-law, is a political career of his own. In a 2004 profile piece, New York Magazine reported he has a framed picture of JFK in his office, and refers to him as a major inspiration.
Only time will tell if he will be able to steer his brand away from Trump’s and reshape it as his own. Drawing upon his more liberal upbringing, Kushner could very well help bridge a gap toward more moderate voters. Whether or not this is part of his Master Plan, Mr. Kushner’s personal investment in the campaign will pay dividends in new powerful contacts that he can cash-in on later.
John Paulson – Economic Advisor
This once-little-known hedge fund manager raked in nearly $4 Billion in a single year by betting against the over-inflated housing market. As a result, John Paulson is now a bonafide “whale” on Wall Street. He has built a career on predicting and capitalizing on a bearish turn in the market, and after convincing his investors to go against conventional wisdom and bet against mortgage-backed securities leading up to the bubble burst in 2008, he succeeded in increasing their investment by 590%. He seems to be uniquely skilled at identifying a deflation before it occurs and using it to his advantage, although his political bets have not always panned out so swimmingly.
In 2011, Paulson donated $1 Million to a super PAC that was backing Mitt Romney’s campaign. But as we know, Romney was not able to secure the White House, which is a little ironic, considering Huffington Post recently reported that Donald Trump is polling significantly behind Romney.
Prior to the 2011 Presidential election, Paulson was much more conservative in his political contributions, only dropping $140,000 between the years of 2000 and 2010. Even more intriguing, only 45% of that went to Republicans. The remainder was split 36% and 16% between special interests and Democratic candidates respectively.
Taking this into account, Paulson’s choice to simply chip in $250,000 toward hosting a fundraising dinner for Donald Trump with two other wealthy moguls seems less enthusiastic than his financial support of Mitt Romney. Nonetheless, other than Adelson, Paulson has been one of Trump’s most prominent Wall Street backers. Meanwhile, Paulson has also been investing $1.5 billion in Puerto Rico real estate and urging other wealthy Americans to do the same. He even convinced 80-year-old fellow hedge fund manager, Michael Tennenbaum, to make the move there as his permanent residence.
Now, Trump has placed Paulson on his 13-person team of economic advisors. For someone who has made a killing on betting against assets before they make an abrupt turn and lose value, his involvement seems to spark questions about how Trump envisions this affiliation could ultimately benefit.
Even though Paulson has donated money to help prevent predatory lending after he hit the jackpot on the housing crisis, many question his willingness to so clearly put his own interests below that of the country as a whole. The more convinced Paulson became that the housing crisis would rock our economy to its core, he doubled down and even prevented his clients from forwarding firm emails in order to preserve as much of a stake from the impending spoils as possible. If the sub-prime lending crisis was akin to the British Coming, Paulson, unlike Paul Revere, took one look at the two lanterns in the steeple and decided against taking the “midnight ride” to warn the citizens of America, but instead thought up a way to make a huge amount of money for himself.
Understandably, it was his job to make his investors the most amount of money possible – a job he does remarkably well. But a person with a healthy imagination can easily find themselves envisioning Paulson still doing what he seemed to do best, which was to bet against the people of America as long as it still benefited him and his close friends.
Could betting on Trump be the ultimate bet against America, thereby priming our economy into becoming the ultimate Bear market, in which Paulson is so skilled at making gains from? A house of cards that crumbles to the soundtrack of cash registers ringing? And all the while, Paulson safely observes it all going down from his new investment properties in Puerto Rico, which just so happen to spike in value as mainland ex-pats come flocking? Given how unpredictable this Roulette wheel of a race this year’s election campaign has been, I wouldn’t bet against it. Might I suggest a nice game of skill instead, like Poker?