“Establishment: A group in a society exercising power and influence over matters of policy, opinion, or taste, and seen as resisting change.” —Oxford Dictionary
Early on in his presidential bid, Donald Trump began touting his anti-establishment credentials. When it worked, he ran with it. It was a posture that proved pure gold in the Republican primaries, and was even, in one sense, true. After all, he’d never been part of the political establishment nor held public office, nor had any of his family members or wives.
His actual relationship to the establishment is, however, complex in an opportunistic way. He’s regularly tweeted his disdain for it. (“I wish good luck to all of the Republican candidates that traveled to California to beg for money etc. from the Koch Brothers. Puppets?”) And yet, he clearly considered himself part of it and has, at times, yearned for it. As he said early on in his run for the presidency, “I want the establishment—look, I was part of the establishment. Let me explain. I was the establishment two months ago. I was like the fair-haired boy. I was a giver, a big giver. Once I decided to run, all of a sudden I’m sort of semi-anti-establishment.”
An outsider looking to shake up the government status quo? An insider looking to leverage that establishment for his own benefit? What was he? He may not himself have known.
He once rejected the idea of taking establishment (or Super PAC) money, only—more recently—to seek it; he rebuffed certain prominent establishment players, only to hire others to help him (and fire yet more of them). He’s railed against the establishment, then tried to rally it to his side (even as he denounced it yet again). Now, with the general election only four months away, it turns out that he’s going to need that establishment if he is to have a hope in hell of raising the money and organizing the troops effectively enough to be elected. There, however, is the rub: Power brokers don’t suffer the slings and arrows of “outsider” scorn lightly.
As a result, if he now needs the establishment more than he’d publicly admit, it may not matter. He may find himself ostracized by the very party he’s set to represent.
Once upon a time not so long ago, making America great again involved a bankroll untainted by the Republican political establishment and its billionaire backers. There would, The Donald swore, be no favors to repay after he was elected, no one to tell him what to do or how to do it just because they had chipped in a few million bucks. But for a man who prides himself on executing only “the best” of deals (trust him) this election has become too expensive to leave to self-reliance.
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One thing is guaranteed: Donald Trump will not pony up a few hundred million dollars from his own stash. As a result, despite claims that he would never do so, he’s finally taken a Super PAC or two on board and is now pursuing more financial aid, even from people who don’t like him. Robert Mercer and his daughter Rebekah, erstwhile influential billionaire backers of Ted Cruz, have, for instance, decided to turn their Make America Number 1 Super PAC into an anti-Hillary source of funds—this evidently at the encouragement of Ivanka Trump.
In the big money context of post–Citizens United presidential politics, however, these are modest developments indeed (particularly compared to Hillary’s campaign). To grasp what Trump has failed to do when it comes to funding his presidential run, note that the Our Principles Super PAC, supported in part by Chicago Cubs owners Marlene Ricketts and her husband, billionaire T.D. Ameritrade founder J. Joe Ricketts, has already raised more than $18.4 million for anti-Trump TV ads, meetings, and fundraising activities. (On the other hand, their son, Pete, Republican Governor of Nebraska, has given stump speeches supporting Trump.)
To put this in context, that $18.4 million is more than the approximately $17 million that all of Trump’s individual supporters, the “little people,” have contributed to his campaign. (He is no Bernie Sanders, who raised $220 million from individuals in the 2016 campaign season.) Even with all his wealth, Trump is in a funding nightmare, lacking the confidence of the Republican Party and its most generous loyalists.
To be sure, other establishment billionaires have expressed support for Trump, like funding kingpin Sheldon Adelson, who said he’d fork over $100 million to the Trump cause. It’s just that he hasn’t done that yet. Chris Christie is similarly trying to help raise funds for the campaign. But the man-who-would-be-veep hasn’t had much luck. So far, at least, Trump’s biggest establishment supporters have been more talk than action.
The Trump Team
In addition to the usual money not flowing in from the usual crowd, there’s the issue of actually preparing to staff a future administration with the usual people, not to speak of the seasoned set of advisers that normally surround presidential candidates. Increasingly, it seems that they may not be available or have already left the proverbial building—and that’s a problem.
Trump has vowed to fill his administration with “the best people.” (In a perfect world, they would, of course, be his clones.) Yet so far he’s been pursuing what he has characterized as a “lean” strategy, which means that few are yet on board and it’s getting late in the game to fake it.
Usually by this time in the election cycle, nominees have pulled together their inner circle, mostly from well-known or rising establishment players, including policy wonks by the bucketful. He hasn’t. According to Vin Weber, a DC-based partner at Mercury, which bills itself as a global, high-stakes public strategy firm, who crafted Mitt Romney’s “policy shop” in 2012, the lack of infrastructure is unprecedented. Romney’s policy shop was first formed 18 months before the 2012 election and fine-tuned in January 2012. We’re in July 2016 and from Trump on this score—nothing. Nada. “Nobody in Washington that I know of,” Weber says, “is assembling a staff for an incoming Trump administration.”
Given his public war with his party, Trump may find himself without anyone left to fire. It’s one thing to cut back on government, another to have no one around to do anything.
Maybe winging it on national policy and disparaging those who might someday make such policy is endearing in The Donald, but not to the Washington establishment. Whatever the case, it might be useful before the Republican convention, which already promises to be a bizarre spectacle, to consider who Trump’s “best people” are—and aren’t—at the moment. Who are his most loyal advisers and supporters? Who would take a political bullet for him or put that bullet in him?
For the answers to such questions, it’s necessary to consider three categories: blood, money, and power. In the land of Trump (and Clinton), of course, blood—that is, family—comes first; financial interests, second; and the political power-elite (a.k.a. the establishment), last.
For Trump, family is foremost; general-election finances are still remarkably lacking; and that final group remains infinitesimal, given how big the Washington establishment actually is. And do note that this has not been because The Donald hasn’t tried to broaden his establishment support. He just seems congenitally unable to succeed at it. It’s a deal he can’t broker. His supporters may think of him as one of them, but his outsider status has come about by default, not by strategic choice, and it shows.
Trump’s most loyal support comes from his family who make up his core “board of advisers.” They are anything but inside-the-Beltway types. If, however, he were to make it to the Oval Office, they could certainly be the new Clintons, the latest bloodline in Washington.
So from family to finances to establishment, here’s a rundown on key players in Trump World, who’s up and who’s down, who’s in and who’s out.
Trump’s Establishment Gets on Board
Ivanka Trump, campaign adviser
Omnipresent in his campaign, daughter Ivanka is the executive vice president of development and acquisitions in the Trump Organization. She “actively participates in all aspects of both Trump® and Trump branded projects.” The presidency is, of course, the ultimate branded project and were the economy to fall off a cliff one Trumpian day, the White House might make the perfect Trump luxury condo building.
For all practical purposes, Ivanka, not wife Melania, is Trump’s “first lady” (in waiting). She appeared on the presumptive board of The Apprentice and Celebrity Apprentice. It was widely rumored that she was the one who had the clout to get Corey Lewandowski, the campaign manager who lifted Trump to victory in the primaries, fired. Put another way, the “establishment apprentice” got the shaft because he crossed the person with the real power in Trump’s campaign.
Jared Kushner, Campaign Adviser-in-Law
Ivanka’s husband, real-estate developer Jared Kushner, tried to persuade one and all that his ownership of the New York Observer didn’t make the paper’s endorsement of The Donald any less objective.
Before the turn of the twentieth century, the Stillmans (bankers) married the Rockefellers (industrialists) to breed young Stillman-Rockefellers who controlled a chunk of the banking sector for decades while advising multiple presidents. Depending on the fate of Donald Trump’s presidential bid, perhaps the 2009 Jared-Ivanka merger (wedding) will someday be seen in the same light. It was, after all, witnessed by an array of movie stars, television personalities, and politicians like former New York City Mayor Rudy Giuliani and present New York Governor Andrew Cuomo.
If Trump is elected, Kushner could wind up appointed, say, Secretary of Real Estate. (Okay, that post doesn’t actually exist—yet.) Kushner set up critical meetings between Trump and key Republican dignitaries and leaders that were meant to elevate his father-in-law’s relationship with the party establishment.
In early May, the New York Times reported that “Donald J. Trump has asked his son-in-law, Jared Kushner, to begin quietly compiling a blueprint for a transition team should he win the White House in November.” If his recent actions are a guide, Kushner will undoubtedly try to snag some significant establishment players as the race progresses.
Paul Manafort, New Campaign Manager
Manafort, a man of controversy, comfortable with wealth and luxury (though refusing any cash compensation for being on the Trump Train), has 40 years of work for the Republican Party establishment under his belt. In addition to being a former principal at the lobbying firm of Black, Manafort, Stone, and Kelly, he played a leading role in George H.W. Bush’s nomination at the 1988 convention, Bob Dole’s in 1996, George W. Bush’s in 2000, and John McCain’s in 2008.
For a campaign selling anti-establishmentism, having a manager from the inner circles of DC might seem like sheer Trumpocrisy, but such seeming contradictions are the essence of The Donald.
Manafort, by the way, has kept an apartment in Manhattan’s Trump Tower, which, as we know, is “one of the world’s elite luxury residences, catering to public figures, athletes, celebrities, and other affluent sophisticates.” In other words, he’s establishment with a view.
Michael Glassner, deputy campaign manager
Glassner is another classic insider. An adviser to the George W. Bush campaign of 2000, he became a top adviser to Sarah Palin in the 2008 election (which may have been a recommendation in Trump’s eyes). He had also once been an adviser to Bob Dole and the Southwest regional political director for the American Israel Public Affairs Committee. Glassner is one of the small team of Trump’s establishment guys reportedly responsible for his chaotic preparations for the Republican National Convention in Cleveland.
Donald F. McGahn II, chief legal counsel
McGahn, one of Washington’s best-connected lawyers, is legal counsel for Trump and a partner at Jones Day, the elite law firm that lists anti-trust and government regulation as its top specialties. By February 2016, the firm had already received more than $500,000 in payments from the Trump campaign.
According to MSNBC’s Zachary Roth, McGahn “was a crucial player in creating the out-of-control campaign finance system that his boss now denounces.” He has helped connect Trump with Republican congressional leaders at his DC offices, further dispelling the myth that Trump is anti-establishment.
Steven Mnuchin, national finance chairman
Not to be outdone by Hillary’s Wall Street connections, Trump recently bagged a former Goldman Sachs partner to run his fundraising operation (the one he used to say he didn’t need). In terms of Mnuchin’s own political contributions, like the firm he once worked for, he’s spread the wealth around. He donated to both Romney and Obama. He also contributed to Hillary Clinton’s Senate and presidential campaigns. In 2012, he donated $20,000 to the Republican National Committee. Overall, Mnuchin has contributed more than $120,000 to political groups over the past two decades, slightly favoring Democrats.
Shades of Trump, according to Variety, he left Relativity Media, where he had been a co-chairman, two months before it filed for Chapter 11 bankruptcy in 2015. He also led a group of billionaire investors that took over beleaguered California bank IndyMac from the FDIC at a bargain price during the financial crisis, profiting, that is, from the pain of California’s foreclosure victims.
Who’s Gone From the Trump Train?
The list of those who have jumped off or were thrown from the Trump train is also heavy on establishment types, though most weren’t exactly from its crème de la crème. Among them were:
Corey Lewandowski, former campaign manager
Lewandowski developed his establishment muscle working for various Koch brother initiatives and was legislative political director of the Republican National Committee in 2001. He had also worked for three congressional representatives and, most recently, the conservative advocacy group Americans for Prosperity, a Koch brothers–funded organization.
According to The Wall Street Journal’s analysis of Federal Election Commission documents, Lewandowski was “paid $20,000 a month”—the equivalent of an annual salary of $240,000, “or 45% more than 2012 GOP nominee and multimillionaire Mitt Romney paid his senior staffers.” He was involved in a notorious incident with a female Breitbart reporter. It seems that, organizationally, he lost out to Paul Manafort, alienated Ivanka, and in June was fired by Trump. He hit the tracks running—CNN promptly hired him as an on-air analyst for a reported $500,000.
Stuart Jolly, former national field director
Jolly resigned on April 18. He had previously worked at the Oklahoma chapter of the Koch brothers’ flagship group, Americans for Prosperity, and also at the Education Freedom Alliance, an organization focused on expanding school choice and free-market economics.
Upon leaving he offered this advice to Trump: “My hope is that you will continue to listen to those who have propelled you to victory.” However, he soon returned as a national adviser for political and fundraising activities at the pro-Trump Super PAC Great America.
Roger Stone, former top adviser
Stone, too, has been an establishment GOP operative for decades. In 1974, he left his position as staff assistant for Senator Bob Dole amid controversy over Nixon White House “dirty tricks.” Five years later, he co-founded the National Conservative Political Action Committee where he developed a knack for creating negative campaign ads. Before he resigned from the Republican Party on his blog in 2012, he had worked on 12 Republican presidential campaigns.
The story of his fate in the Trump campaign is murky. The Donald insists he fired Stone, while Stone insists that he was the one who said, “You’re fired!”
Rick Wiley, veteran Republican adviser
An establishment player and a former political director for the Republican National Committee, he was removed as Trump’s national political director in May 2016, two months after having been brought on board by Paul Manafort. The media cited various unnamed sources offering various reasons why. Whatever the explanation, he was in and then he was out, because measured thinking about position selection isn’t a Trump priority. Wiley now works for the Republican National Committee.
Who Doesn’t Want to Be Seen at Trump Station?
The list of establishment players exhibiting no interest in associating with The Donald or an absolute animus against him seems to expand by the day. It includes, of course, Mitt Romney, Jeb Bush, George W. Bush, and Lindsey Graham, among so many others—key players all in the Republican Party. Romney typically didn’t mince words, saying, “Donald Trump is a phony, a fraud. His promises are as worthless as a degree from Trump University. He’s playing the American public for suckers: he gets a free ride to the White House and all we get is a lousy hat.”
Romney might be wrong about the hat.
Meanwhile, a troop of prominent Republicans are heading for the hills, not the party’s convention. Congressional representatives are going into opposition; convention delegates pledged to Trump are restless and other delegates are muttering about revolt. A former Republican national-security adviser and a former Republican Treasury secretary (and former Goldman Sachs chairman and CEO) have thrown their support to Hillary, and the establishment cast of characters thinking about heading for the exits continues to lengthen.
If much of the rest of the establishment follows the present pattern and departs Trump Station, what will this election look like? If history is any guide, family is not enough in American politics, only in banking. A candidate needs a party establishment for everything from experience to organization to money.
Trump himself lacks experience in government or public service of any sort. He’s essentially at sea when it comes to what it might mean to govern this country. In this, he is anything but typical among Republican front-runners who became president. William Taft was a former secretary of war. Herbert Hoover was secretary of commerce. Warren Harding was a senator. Calvin Coolidge was his vice president. Dwight Eisenhower was a decorated general. Richard Nixon was his vice president and had been in Congress for years. Ronald Reagan was, yes, an actor, but had also been the governor of California. George H.W. Bush had been a congressman, an ambassador, and director of the CIA. His son was, of course, governor of Texas.
If Trump continues to play the outsider card (as he essentially must, given what his supporters now expect) and continues to alienate ever more of the establishment, he’s likely to find himself fighting a battle of diminishing returns in his own party. And what about that establishment’s money? After all, what’s an election these days but a pile of donated money and backroom deals?
We know he raised significantly less than Jeb, Ted, and Marco and still beat them in the primaries, and that undoubtedly gave him a certain unrealistic sense of what was possible in a presidential campaign. The result: This May his campaign raised only $1.3 million to Hillary’s $42.5 million. If that’s a sign of what’s to come and his supporters, unlike those of Bernie Sanders (the only true populist in the race), don’t begin to up the ante drastically, watch out.
Unsurprisingly, establishment pockets are looking a good deal less deep these days when it comes to him, though Trump has begun to say that he might need to find up to $1.5 billion to run this race. Key establishment money-raising figures have now visibly turned their backs on him, just as he did on them.
The Koch brothers are not atypical in refocusing the future contributions of their Super PACs on Republican races in the Senate and House. Charles Koch even signaled the possibility, however faint, of taking a further step and using his money for the other side. “We would have to believe [Hillary’s] actions would be quite different than her rhetoric. Let me put it that way,” he said in an interview on ABC’s This Week. When asked if it was possible that another Clinton could be better than a Republican, he added, “It’s possible.” (With establishment money, all things are possible.)
Outside groups—PACs and Super PACs on both sides of the aisle—have already spent a combined $34.1 million on Senate and House races, according to a Bloomberg News analysis of Federal Election Commission data. That’s nearly double the amount spent at this point in the 2012 campaign. The Freedom Partners Action Fund Super PAC, a political arm of the Koch empire, has divided nearly $10 million among four key Senate races in Wisconsin, Nevada, Pennsylvania, and Ohio. It has, however, kicked in only $36,000 for anti-Hillary efforts and not a penny for Trump.
American Crossroads, a Karl Rove Super PAC, is also opting to focus on Republicans in the Senate, though so far it has doled out just $100,000 for that effort and $135,000 against Hillary. Rove has called Trump “a petty man consumed by resentment and bitterness,” which tells you all you need to know about where he’s likely to put his outfit’s money this election season.
It’s increasingly clear that the GOP establishment is playing a different end game than The Donald. Whether Trump or Hillary wins, they want a Congress stacked in favor of their needs, and perhaps many of them are looking to a Paul Ryan run in 2020 as their saving grace.
So here’s a question for that ultimate insider of outsiders: Can Donald Trump actually lose the 2016 election? Let’s say Hillary beats him, as the polls of the moment suggest she will. Has he lost? Probably not.
After all, he’s brought his brand to a far broader global audience on a stage so much larger than any Apprentice imaginable. He could lose dramatically, blame the Republican establishment for being mean to him, and then expand the Trump brand into new realms, places like Russia, where he’s long craved an opening. Vladimir Putin and he could golf together bare-chested while discussing the imminent demise of the American empire. “My country could have been great again,” he could sigh, “if only it had voted me in.” His consolation prize: a Trump Casino in Moscow’s Red Square?
In other words, whether the establishment supports him or not, whether he wins on November 8 or not, his brand wins, which means that he triumphs.
Consider this: The Old Post Office building on Pennsylvania Avenue with views of the White House is already wrapped in blue Trump International banners as it’s being converted into a luxury hotel. Due to open two years ahead of schedule and two months before Election Day, it’s one of Ivanka’s projects. It ensures that her father has branded the avenue regardless of whether he ends up in the White House or not. Given the property’s location and what its “presidential suite” is sure to look like, working in the Oval Office might prove to be a downgrade.