By Jonathan Swan - 01/10/16 05:10 PM EST
Republican mega-donor Sheldon Adelson has joked privately that he belongs to a divided household: He likes Florida Sen. Marco RubioMarco RubioClinton’s strategy: Get under Trump’s skin Rubio, Heck help out at car crash scene Florida paper endorses Clinton, writes separate piece on why not Trump MORE and his wife Miriam likes Texas Sen. Ted CruzTed CruzJudge rejects attempt to stop internet oversight transfer Tech groups file court brief opposing internet transition suit Cruz criticizes federal law enforcement on terrorism MORE.
But the truth, more than half a dozen sources close to Adelson say, is more complicated. The casino owner, who together with his wife spent nearly $100 million in the 2012 campaign cycle, is still weighing his options.
“The guy is cagey,” said a conservative leader with ties to the donor community who spoke with Adelson recently. “He said ‘I like Rubio.’ He did not say ‘I support him.’ … But he also said that his spouse feels more strongly about Cruz.”
Funded almost entirely by Adelson, the former House Speaker assaulted and nearly destroyed the ultimate nominee, Mitt Romney, through negative ads that some believe cost Romney the presidency.
So despite speculation that Adelson’s formal endorsement of Rubio could come as soon as last October, the billionaire is biding his time.
He still meets with and talks regularly to Cruz and has told sources he likes what both Cruz and Rubio are saying. He is particularly taken by Rubio’s hawkish foreign policy positions. He has also met several times with Jeb Bush's campaign and has been reassured, after an early stumble, that the former Florida governor will staunchly defend Israel — the subject the billionaire cares about most.
All three campaigns claim to be optimistic about winning Adelson's support, but sources close to the billionaire say he is thinking about the race in a more pragmatic way than in 2012, when he had a deep loyalty to Gingrich.
Above all, Adelson has told his confidants that he is determined to win this time and has hinted that it might be unwise to throw his lot in too early on a candidate who can't beat front-runner Donald Trump.
Gingrich says he hasn't spoken to his friend about the billionaire's spending plans for 2016 but said in a telephone interview with The Hill that 2016 candidates lack the years of personal friendship he had when Adelson supported him in 2012.
“I suspect what he's doing now is sitting back and watching,” Gingrich said.
"Think about it as an investor," he added. "You've got four to five centrist conservatives sitting out there. You don't have any idea which one could emerge."
Adelson's political adviser, Andy Abboud, declined to comment for this story.
Sig Rogich, a veteran Nevada Republican strategist and finance chair of Bush’s campaign in that state, said that even though he knows Adelson well, he would never claim to know what the casino owner is thinking. This was a comment repeated in off-the-record conversations even with a source who works for Adelson.
Although he hasn’t spoken about 2016 with Adelson recently, Rogich said he has been left with the impression that the billionaire’s mind is not yet made up.
“I think he will probably wait until the primary process plays itself out,” Rogich said. “That’s what he’s always told me in the past, that he’ll wait until the debates are finalized and wait until the early primary states" have voted.
"Newt and he were very close, so there was a different dynamic there. I think he will wait things out because it’s never too late to get involved when you have resources like that to give.”
A source familiar with Adelson's thinking cautioned, “People who profess to be inside Sheldon's head or know what he's doing I would say are 99 percent full of shit or trying to promote their own self importance.”
The source agreed that Adelson's large and aggressive intervention in the 2012 primaries on behalf of Gingrich probably would not be repeated this cycle.
"The Newt thing, a lot of that was loyalty-driven. They had a friendship that transcended decades. ... That's not the case with these candidates.
"I think he's going to let this process play itself out. I think he wants to have impact but in a way that's constructive and thoughtful and strategic. The landscape [in the GOP primaries] is quite unsettled."
Another source familiar with Adelson's political operation said that people often underestimate how the fortunes of his casino interests affect his willingness to give money to politicians. Part of Adelson's current caution, the source suggested, is the recent damage to his casinos in Macau, where the Chinese authorities are targeting high-roller gamblers in an anti-corruption crackdown. The Sands share price has been falling, and billions have been wiped off the market cap.
"The business side affects his general disposition," the source said. "When he's doing well the sky's the limit and he feels better about giving." And when things are going badly — as they are currently — Adelson questions even $2 million political investments, the source said.
Adelson has so far this cycle only been reported by the Federal Election Commission to have made nominal contributions to the campaigns of Rubio and former presidential candidate Sen. Lindsey Graham (R-S.C.).
But he is known as such a cagey operator that even those in his close political orbit say they cannot be sure he hasn’t already made a secret payment to a social welfare non-profit that supports a particular candidate.
Such a vehicle, organized under section 501(c)4 of the tax code, would allow Adelson to hide his identity from the public. The most obvious venue for Adelson’s cash would be the non-profit supporting Rubio, Conservative Solutions Project, which claimed to have raised nearly $16 million by early July.
Conservative Solutions Project spokesman Jeff Sadosky would not comment on the group’s donors.
Still, if Adelson has already made a secret multimillion-dollar payment to a candidate, it is unknown even to some who work for him at senior levels. And it would also be an extraordinary move, given he is still meeting with candidates and leaving them — particularly Cruz — and their associates with the impression that he remains undecided.
He also met with Trump during the recent Republican debate at Adelson’s Venetian Hotel in Las Vegas. Trump's campaign manager, Corey Lewandowski, sat in on the meeting and told The Hill, “Mr. Trump has said that he's not seeking financial support from Mr. Adelson but that he would be honored to have his support in the voting booth.”
Lewandowski said he got no indication of Adelson’s intentions.
In conversations around that period, Adelson consistently suggested one thing: He badly wants to win this election and is prepared to spend what it takes to do so.
With a net worth estimated by Forbes to be $23 billion, Adelson can afford to spend a lot. And freed from personal obligations of friendship, he can hold off and enjoy the courtship until he feels confident that he has a candidate who can win.
"At the end of the day,” said a source who speaks to Adelson regularly, “he wants somebody he can agree with on the issues.
“But winning is the most important criteria.”