Donald Trump speaks at a briefing with senior military leaders in the Cabinet Room of the White House (Getty/Andrew Harrer)

Donald Trump and his shady entourage — a brief history

With friends like these...


Jonathan Z. Larsen
December 22, 2018 12:30AM (UTC)
The original article appears on WhoWhatWhy.org.
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It has often been observed that President Donald Trump behaves more like a mobster than an executive, let alone a statesman. Perhaps it is not so surprising.

Both his grandfather and father were “rough customers.” During the Gold Rush, his grandfather Friedrich Trump allegedly operated hotels full of “sporting ladies” for the enjoyment of prospectors.

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To help him run his real estate business, Trump’s father, Fred, picked an associate of two prominent mob families as his partner. “Decades later,” writes David Cay Johnston, “Donald Trump would also do business with the heads of those same families, though at a remove, developing numerous business connections with an assortment of criminals.”

And then there were the merely shady people with whom Trump surrounded himself throughout his life, and now as president.

The media seemed perplexed when Trump picked the elegant dandy Paul Manafort as his campaign chair in the spring of 2016, but in truth Manafort was just as comfortable in a world of thugs as Trump himself — he had worked for so many of them. Before he got to Trump, Manafort had become infamous for putting lipstick on pigs — dictators, tyrants, and autocrats all, among them Marcos of the Philippines, Mobutu of Zaire, Savimbi of Angola, and Yanukovych of Ukraine.

Behind the face cards of Trump and Manafort stood a rogues’ gallery of operatives more than happy to serve in the shadows. As special counsel Robert Mueller files his papers in court, with each day it is becoming more and more obvious that Trump would probably not be president today were it not for the combined efforts of these chimerical figures. Almost all have a prior history in the darker recesses of Republican political campaigns stretching into the past century.

Here are brief introductions and timelines for some of those who have emerged from the shadows to make their cameo appearances in the ongoing Mueller investigation.

2000: Roger Stone and Bush v. Gore

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A longtime friend of Trump, a lifelong political operative, and a former lobbying partner of Paul Manafort, Roger Stone began 2000 as head of Trump’s half-hearted presidential bid, and ended it playing a crucial role in getting George W. Bush elected.

It was Stone who led the infamous “Brooks Brothers riot” on the ground, sending Republican congressional staffers to Florida to stage phony “grassroots” protests outside the offices of state election officials. These raucous manifestations of a supposed “public uprising” led to the suspension of a vote recount in crucial Miami-Dade county.

When the Supreme Court stopped the recount midway in the case Bush v. Gore, the Republican majority on the court effectively supplanted the voters and appointed Bush president by fiat. As we will see, that may have not been the last time Stone affected a presidential outcome.

2004: Jerome Corsi and the Reelection of George W. Bush

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By rights, President George W. Bush, by then highly unpopular as it became more and more clear that the justification for his Iraq intervention, weapons of mass destruction, was bogus, should have had no better chance of reelection than his father before him. But W. eventually beat John Kerry by some 3,000,000 votes or so, the same popular vote margin by which Hillary Clinton bested Trump in 2016 while losing in the Electoral College. One major reason for Kerry’s loss was an ad hoc group called Swift Boat Veterans for Truth that was heavily funded by Dallas friends of Karl Rove and the Bush family. Dallas oilman T. Boone Pickens alone threw in $4 million, adjusted for inflation.

The man who helped put the Swift Boat fraud into the national conversation was Jerome Corsi, through his book "Unfit For Command," co-authored with Swift Boat captain John O’Neill.

Corsi’s book and an ad hoc group of Vietnam veterans would argue that Kerry did not deserve his three Purple Hearts, nor his Bronze Star, nor his Silver Star. Not only did they throw doubt over Kerry’s “specious” medals won during the Vietnam War — as a swift boat captain Kerry had one of the most dangerous assignments imaginable — they also called him a traitor for having testified to Congress in 1971 about atrocities committed by fellow service members; the story of the My Lai Massacre that killed more than 300 women and children had broken two years before.

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The irony of this campaign of vilification was that a bonafide hero of the Vietnam War would lose the election to a man who sat out the war stateside with the National Guard, and in fact never even completed his Guard obligations. (There are irresistible comparisons to be made to draft-dodger Trump trashing the heroism of Vietnam POW John McCain).

2004–2008: Felix Sater, Donald Trump, and money laundering

New York’s Trump Soho, finished in 2008, was built with virtually no money from Trump, but millions upon millions invested by shady operators brought to the deal by Felix Sater and his partners at the Bayrock Group.

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Much of the Trump Soho money came from countries that had been part of the former Soviet Union (FSU). Over the years, figurative freight trains full of freshly laundered FSU money had been invested in various Trump condos, real estate deals, and yachts, but the Trump Soho in particular seemed to be built as much with Russian rubles as it was with concrete and steel.

Felix Sater’s role in the project was well hidden, as were his later efforts to build Trump Moscow (see below). This was in large part because Sater was a convicted criminal whom Trump publicly professed not to know.

The New York Trump Soho was finally completed only by dint of serial lies about the state of its financing and the degree to which its condo units had been sold. Even Trump’s children were enlisted in this fraudulent sales campaign, to the point that the New York District Attorney considered bringing charges, but backed off at the last minute.

2007: Erik Prince, Blackwater, and the Iraq War

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So much went wrong with the Bush-Cheney war in Iraq, but high among the factors was the rogue behavior of a private mercenary force then called Blackwater USA.

Founded by Erik Prince, a former Navy Seal from a wealthy Republican family with connections to the Bush administration, Blackwater eventually landed a $1 billion contract to protect American diplomats running the war effort.

By 2007 Blackwater had become controversial enough that a government investigator traveled to Iraq and wrote in a memo that he had found an environment in which Prince’s security guards “saw themselves above the law.” Two weeks after that memo, Blackwater guards killed 17 Iraqi civilians and wounded 20 in the middle of a square in Baghdad. The horrific incident contributed much to the United States’ deteriorating relations with the Iraqi government.

2008: David Bossie and the 2008 Election

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David Bossie, a college dropout and former firefighter, has been a worker in the trenches for Republican issues for decades. He was one of the first to sign on to Trump’s winning presidential campaign; indeed it was Bossie who recruited Steve Bannon to the cause.

Bossie has prided himself in particular on being a Clinton family “researcher,” and his most prominent book on the subject was produced in time for the 2008 election. Called "Hillary and the Politics of Personal Destruction," this book, among others, would lay the seeds for one of Trump’s most insistent campaign themes in 2016: “LOCK HER UP!” Bossie’s attempts to bring out an anti-Hillary movie based on the book would eventually wind up before the Supreme Court (see below).

Bossie’s name has recently been floated as a possible replacement for John Kelly as White House chief of staff.

2008: Roger Stone and the Fall of Eliot Spitzer

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As attorney general of New York State, Eliot Spitzer had been a relentless prosecutor of local white-collar crime. Few people had better reasons to fear him than Trump, whose company, whose “University,” and whose “foundation” were all shot through with shady business practices, if not outright criminality. (The fraudulent university was eventually shut down by the feds — Trump had to pay $26 million in restitution at the end of the 2016 campaign — and the Trump Foundation is still being scrutinized by the New York attorney general’s office.)

Once Spitzer was elected governor, a group of Republican-aligned power brokers went after him, tailing him with private detectives. They eventually caught him associating with a prostitute, a scandal that forced Spitzer to resign.

In the thick of this effort was Stone, who may well have been tipped off by one of his own prostitute friends. Stone is a notorious swinger and philanderer who has bragged about the high-class escorts he knew. In a well-crafted documentary on the subject, Client 9, Stone winks at the role he might have played in Spitzer’s fall from grace.

As the scandal was breaking, a phone call was made to Spitzer’s father’s house, threatening to bring his whole family down. The phone message was made public and the call was eventually traced to a telephone. It was Stone’s.

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2010: David Bossie and the Supreme Court

David Bossie has long been associated with an organization called Citizens United, and it was this enterprise that would give the name to one of the most ill-considered decisions ever made in the history of the Supreme Court.

The case that Bossie’s company brought before the court was its right to distribute its highly partisan "Hillary: The Movie" in the midst of the 2008 election, in conjunction with Bossie’s book "Hillary and the Politics of Personal Destruction."

A lower court had ruled no. In its Citizens United v. FEC decision, the Supreme Court disagreed, arguing that corporations are “people too” and thus have First Amendment rights like the rest of us, thus allowing corporate executives to spend as much as they wanted, whenever they wanted, to effect political outcomes.

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As one can well imagine, this has proved to be a game changer for democracy going forward. At the same time Citizens United narrowed the legal concept of corruption down to an absurdity — an observable exchange of goods or money for political acts. The court’s decision not only opened elections to a flood of dark money from hidden sources, but made prosecutions for buying political influence all but impossible.

2011: Jerome Corsi and the so-called "Birther Movement"

Just as he had defamed Kerry in 2004, Corsi, through a new book entitled "Where’s the Birth Certificate?", sought to throw similar shade on Barack Obama, the sitting president of the United States, claiming he was not a US citizen and therefore his election had not been legitimate.

Donald Trump immediately picked up on this flimflam, beat it to death for years on national television — why did the media give him that air time? — and eventually rode it into the 2016 presidential primaries.

By the time he had disavowed Corsi’s Birther Movement — ever so reluctantly — he was the Republican nominee, running on a campaign of racial division and white nationalism, the very issues that had been greatly inflamed by Corsi’s book.

2016: Roger Stone, Jerome Corsi, and WikiLeaks

Some close observers of the 2016 presidential election believe that the dump of hacked Democratic Party emails in the summer of 2016, and, later, the Chinese-water-torture release of Clinton campaign chair John Podesta’s hacked emails, played a vital role in the election’s outcome.

The very word “email” conjured up the now old scandal over Hillary Clinton’s private email server — the subject of congressional and FBI investigations — and the new hacked emails now served to further inflame Bernie Sanders supporters and sow further doubt among potential Clinton voters.

During the campaign, Trump would claim it was impossible to know who leaked the emails — perhaps the Chinese, perhaps a “four-hundred pound man sitting on his bed.”

It now appears likely that the Trump campaign knew all along that Russia had indeed hacked them, and had moved swiftly to seize them and deploy them.

Campaign chair Manafort, his old friend and lobbying partner Stone, and Swift-Boater and Birther Movement’s Corsi may have all played key roles in this effort, not just to find out everything they could from WikiLeaks about its email trove — but to enlist Julian Assange as a silent partner in Trump’s election.

The first tranche of Podesta emails, in fact, would drop just hours after Trump’s Access Hollywood tape became public. If that was not a beautifully orchestrated dump — like dropping balloons that had been long held suspended in a giant net at the end of a victorious election — then it was a mighty odd as well as a convenient coincidence.

2016: Michael Cohen, Felix Sater, and the Moscow Tower

Through the fall of 2015 and until June of 2016, these two men would try to arrange for the building of a Trump Tower “East” in the middle of Moscow.

Trump had been trying to build in Russia for 30 years without success. Now his organization sought not only permission from the Russian government but also financing through Russia’s state bank to build Trump Moscow.

To further Trump’s cause, Michael Cohen and Felix Sater allegedly dangled the notion that Putin might be given the penthouse, worth an estimated $50 million. All of these efforts were hidden from the public once Trump’s presidential campaign started in earnest.

Interestingly, during the Trump transition, Cohen and Sater would prepare for future National Security Adviser Michael Flynn a plan to lift US sanctions on Russia.

Without the lifting of sanctions, no Trump project in Moscow would have been possible. Were sanctions all along the quid pro quo at the heart of the alleged Russia-Trump collusion?

2016: Erik Prince, Hillary Conspiracies, and the Seychelles Meeting

After selling Blackwater USA in 2010, Erik Prince established other mercenary ventures. Both he and his sister, Betsy DeVos, the future secretary of education, were major donors to the 2016 Trump campaign — but Erik was otherwise all but invisible.

He could be heard on Breitbart, angrily spouting wild, unsubstantiated allegations about the Clintons, including sex slaves being held on remote islands, but that just made him another right-wing kook.

Then it slowly emerged that Prince had been playing a role behind the scenes. The one-time intern to California Congressman Dana Rohrabacher — he of extreme pro-Russian views — Prince had met privately during the 2016 transition in the Seychelles with Kirill Dmitriev, a Putin ally and the head of Russia’s Direct Investment Fund.

People mostly go to the Seychelles islands to watch birds. Was Prince serving as Trump’s bagman? Was he establishing a Russian back channel for the White House? Had he lied to Congress when he told the House Permanent Select Committee of Intelligence “I didn’t fly there to meet any Russian guy”?

George Nader, a Lebanese-American businessman and a former Blackwater agent, told Mueller that he had indeed set up a meeting between Prince and Dmitriev, and had even met with Prince in New York the week before to brief him on the get-together.

This spring the New York Times revealed that Prince, at the height of the presidential campaign, met with Don Junior and an emissary for “two wealthy Arab princes” from Saudi Arabia and the UAE to discuss their help in winning the election.

All the while, Prince has been trying to convince Trump officials that the war in Afghanistan should be turned over to a private security force. He has one in mind — a new mercenary firm he would lead.

If Prince had been doing special favors for the Trump campaign behind the scenes, could his sister’s cabinet appointment have been the payoff?

So many shadowy characters. So many questions. Mr. Mueller?


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