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An Honest Liar: Meet The Wonderkid Behind Trump's Unlikely Rise

WHEN HE WAS 16-YEARS-OLD, Sean Moskowitz was robbed at gunpoint by a group of African-American men outside of the Sawgrass Mills Mall.

That isn’t true, but it is an anecdote the now 31-year-old tells those that interview with him for a job on Donald Trump’s campaign staff. “It’s a Rorschach test I use to suss out saboteurs or, even worse, the weak," says Moskowitz in his overtly affected voice. "If an applicant responds with sympathy, or in a way that I feel excuses the behavior of my fictional delinquents, I won’t have them on my staff. But if they respond with anger and focus on, shall we say, the complected characteristics of the criminals, then they may just have the constitution necessary to help keep “Crooked Hillary” out of the White House.”

Moskowitz was named as Donald Trump’s campaign director this week following Corey Lewandowski’s ouster and is, like most things this election cycle, something of a political anomaly: He is an honest liar.

He is, for example, the first to acknowledge that Trump’s political ascension may not be the catholicon that his supporters are expecting. “Donald Trump may very well be “bad” for the country” says Moskowitz, his legs perched on the oversize mahogany desk that occupies his off-the-greens war room at Trump’s Doral National golf course. “But I don’t care,” he quips in a faux-Texas drawl so as to imitate Tommy Lee Jones’s response to Harrison Ford’s plea of innocence in The Fugitive.

“Mr. Trump is paying me to get him elected. Period. And that is exactly what I am going to do.”

MOSKOWITZ WAS RAISED IN A WEALTHY, MOSTLY WHITE NEIGHBORHOOD in Moorestown, New Jersey. As he talks about the country, its problems, and Trump’s solutions for restoring a vague notion of greatness to it, one cannot help bear his upbringing in mind. This is especially true when he speaks harshly of society’s most disadvantaged citizens or drops, with surprising regularity, the word “nigs” when speaking about African-Americans, a term he insists is not racist and that he uses with his unnamed black friend.

By all accounts a shy and introspective child, Moskowitz moved to Boca Raton with his parents when he was 15-years-old after his father, renowned periodontal surgeon Dr. Hershel Moskowitz, moved his practice to the wealthy, mostly white South Florida community. The move was in part motivated by the changing demographics of Moorestown, which Sean’s father believed would have a negative impact on his professional practice and his son’s upbringing.

The move proved hard on the diminutive adolescent. “Sean was so small growing up, but he had a nice set of friends that had his back in Moorestown," said his mother Gillian, a housewife and fitness enthusiast. "When we moved to Florida, he didn’t have anyone. He would be picked on because of his height and would come home crying. It was just heartbreaking.”

It was after a particularly hard day at school that Sean received advice from his father that would forever change his outlook on life.

“My dad sat me down and told me that I would almost always be the smallest guy in the room. He said if I wanted to make it in this world, I needed to act big. From that moment I decided I was going to walk into every room like I was the biggest, smartest, and most ruthless guy on the planet.”

Beginning in high school Sean started to dress and act differently. His father, who himself stands at an equal 5-foot-6-inches, purchased his son an expensive wardrobe, submitted him to hours of private tutoring, enrolled him in acting classes to improve his articulation and confidence, and made him join his school’s cheerleading squad.

“It was so counterintuitive. It was genius” said Sean of his father’s insistence that he cheer. “When I signed up, I caught so much grief for it and really thought I was undoing all of my work to improve my status. But my dad insisted, telling me the best thing I could do for myself was join the squad. That’s when I learned to take a long-term view of things and not get too caught up in the initial controversy or embarrassment of a decision.”

“I felt it was important for Sean to learn how to "interact with women". Being the only male member of a cheerleading squad certainly has its advantages,” said Dr. Moskowitz, who was himself a cheerleader and who insisted that he had a number of sexual encounters with his teammates on overnight cheerleading trips. “I think my boy did all right for himself,” gloated the doctor, “like father, like son.”

AFTER HIGH SCHOOL, Sean enrolled in Drexel University to study finance. He also joined the school's cheer squad, where he met freshman cheerleader Dory Freedman of White Plains, New York. It was through Ms. Freedman that he first became interested in politics.

“Sean was so awkward when I first met him,” chuckled Ms. Freedman. “Here he was, this little tiny boy, who was sort of prematurely balding but nevertheless shockingly over-confident. I remember he dressed like he was always just about to board a yacht. It was the funniest thing. It would be 30 degrees outside and he would wear a bright yellow shirt with his collar popped, deck shorts, and a pair of Sperry Top-Siders and would go out of his way to insist that he wasn’t cold.”

During the winter of 2007, Dory started volunteering for the Obama for America campaign. Sean, whose personal political philosophy at the time could be described as apolitically right leaning, would accompany her to meetings.

“He would follow me around to these Obama events and go canvassing with me,” said Ms. Freedman, who insisted her relationship with Sean was strictly platonic. “He asked me out all of the time, but I just couldn't see myself with him. Not because of his looks necessarily, but because he was always just trying too hard to impress me. He would say and do anything. I think maybe that is why he got so involved with the Obama campaign. He thought if he became political I would start to like him.”

As an Obama volunteer, Sean became fascinated by the data concerning likely voters and started to pay special attention to those factors which would repel voters away from his candidate. “The type of insights you could read from the data was incredible," said Moskowitz. "For instance, if you were a white person that lived in a suburban community less than 15 miles away from an urban area with at least a 40% African American or Hispanic population, there was a greater than 70% likelihood that you voted for John McCain. That same group split almost evenly four-years earlier in the Bush/Kerry election. I found that the most statistically significant factor to explain these types of differences was the voters' views on race.”

Following Obama’s election, Moskowitz, who had become a political science major and washed out of Drexel's cheerleading program after injuring his back while trying to demonstrate that he could do a back-handspring to a crowd while standing on icy pavement, authored a paper titled "The Politics of Fear and Race" that made headlines among politicos for its conclusion that the failure of McCain’s campaign was not its inability to attract African American or Hispanic voters, but its powerlessness to mobilize, through rhetoric and coded language, the still majority white population of the country that is frustrated about or afraid of their declining social primacy.

“The trick,” Moskowitz concluded in his paper, “is to shroud the campaign’s message in language that evokes an undefined nostalgia, rather than explicit racial terminology.” As an example of the type of slogan that could be effectively used to rally the white masses, Moskowitz suggested “Make America Great Again.”

“I should have trademarked that phrase,” Moskowitz says with a smile.

AFTER LEAVING DREXEL, Moskowitz became a man without a home. Obama for America refused to hire him for the reelection campaign partially because his article had received a significant amount of press among conservative pundits and became something of a how-to guide for Tea Party candidates during the 2010 midterm election, but also because of numerous complaints filed during the 2008 campaign against Moskowitz regarding allegations from female staffers and volunteers that he had become sexually aggressive toward them. On advice from counsel, Moskowitz refused to answer any questions regarding these uncharged allegations, but according to an internal Obama for America memorandum, there were at least three separate incidents during the 2008 campaign in which Moskowitz allegedly took advantage of women who were under the influence of alcohol or drugs.

The self-described wonderkid also found himself blacklisted from Mitt Romney’s 2012 campaign, again partially on account that his article had become a point of controversy among GOP mainliners who advocated a long-term Republican strategy of appealing to non-white voters, but also to avoid the liability associated with Moskowitz’ reputation.

“We were very seriously considering bringing him onboard,” said a senior Romney campaign staffer who agreed to speak on the condition of anonymity. “He is a very intelligent young man with unique political views. But we couldn’t get one person to attest to his character. Even his own references described him as ruthless and obnoxious. Couple that with the serious sexual allegations made against him and we determined bringing him on was too much of a liability for the campaign.”

Unsure of his next move, Moskowitz enrolled in law school at the University of Miami to regroup. It was during this time period, some might say serendipitously, that he also took up golfing at the course that his office now overlooks.

IN NOVEMBER OF 2014, third-year law student Moskowitz was seated at the restaurant in the Trump National clubhouse when the course’s owner, Donald Trump, joined a man at the table next to him. That man was Trump’s soon-to-be campaign director Corey Lewandowski. It was more than six-months from Trump’s official campaign announcement.

“I was trying to act nonchalant when Trump walked in, but when he sat next to me I couldn’t help but listen. It was really interesting because they were talking about some political race and Lewandowski kept telling Donald that the key was to mobilize white voters by exploiting their fears about race and immigration and terrorism. It was as if he was reading right out of my article. Then I looked over and saw that he actually was reading out of my article, which was sitting on the table in front of him.”

Feeling as if fate were compelling him to introduce himself, Moskowitz walked over to Trump and Lewandowski’s table and introduced himself as “the mastermind behind the strategy the two of you have been discussing.”

“To my shock, and as if my introduction was totally expected, Donald replied ‘well you better have a seat then,’ and before I knew it I was helping him formulate what would be his primary electoral strategy." It was at this initial hours-long meeting that Trump decided to crib Moskowitz's Make America Great Again slogan, formulated his rhetoric about building a wall to stop immigration from Mexico, and first flirted with the notion of banning Muslims from the Country.

"Donald was really the first person who understood what I had been saying since 2008. A campaign becomes unshackled from the day-to-day controversies and pitfalls of modern "p.c." sensibilities if they abandon what I call "coalition politics" in favor of appeals to the still powerful white working-class majority. By focusing solely on energizing the base, rather than spending needless energy and money trying to widen the tent, you can use language so incendiary that the media will have no choice but to cover it and help spread the message. It was the perfect strategy for a person like Donald."

That night, Moskowitz sent the dean of his law school a note that he was withdrawing and started working as Mr. Trump’s deputy political director.

WITH LEWANDOWSKI’S FIRING last week, Moskowitz was promoted to the campaign’s political director, and the mind charged with orchestrating Trump’s uphill battle against Hillary Clinton for the Presidency.

“This election poses some challenges for Trump, and there have been a few mistakes, but luckily he is running against probably the weakest candidate the Democrats could have nominated. Statistically speaking, Donald Trump needs to win 65% of the white vote in order to win the Presidency. That is about 5% better than Romney did in 2012. Now, I’m willing to bet there are at least 5% of Obama voters who fundamentally do not trust Hillary Clinton. The game is to get those folks out to vote.”

Moskowitz’ plan for engaging the untapped white voter? Continue to paint Clinton as a dishonest, Washington insider that is unconcerned about what he calls “the ethnic dangers” of the world.

“White America is concerned about Muslims blowing them up, black people rallying in the streets, and immigrants taking their jobs. If we can focus on those issues for the next 5 months, and continue to say whatever we need to say so the American people believe Clinton is responsible for those problems, then we will win. The numbers don’t lie.”

"A couple more well-timed ISIS attacks, preferably domestically, will also help. White voters get really engaged around domestic terror and firearm restrictions, both of which become points of focus following an attack."

When asked how it felt to quietly hope for more attacks on American civilians in order to benefit Trump politically, Moskowitz turned glib. "Jesus Christ, I have a job to do. And the fact is terror is good for my business right now. I don't want anyone to fucking die, but if some do, I hope that it happens the week before the election."

MOSKOWITZ SPENDS MOST OF HIS DAYS bunkered in his Doral office, pouring over polls and data. Above his desk is a poster of Lee Atwater, the former Republican National Committee Chairman and political operative who invented the win-at-all-cost form of modern racial politics that Moskowitz seems to have perfected. Mr. Atwater, it should be noted, who was diagnosed with terminal brain cancer in 1990 at the age of 39, publicly repented and sought forgiveness for the destruction caused by his divisive political strategies. Moskowitz, gleaming no lessons from Mr. Atwater's deathbed conversion, says there is plenty of time to seek forgiveness. "For now, I have win."

Moskowitz sleeps in a hotel room at the adjoining resort most nights and has, to this reporter's best estimation, almost no friends to speak of. In fact, for this profile the Plantain was unable to find anyone to speak on the record about their friendship with Moskowitz with the exception of Ms. Freedman, who acknowledged that their relationship had grown distant.

“Sean is unabashedly self-interested,” said Ms. Freedman. “That is sort of his charm, I suppose. But it is just so difficult to be around. After I let him know, in very explicit terms, that I would only ever be interested in being his friend, I learned that he was actually incapable of being a friend. He is an angry and lonely person and doesn’t seem to believe in anything. All he wants to do is win at any cost.”

Moskowitz admits that life as a campaign director is hectic, but disagrees with Ms. Freedman’s characterization, insisting that the now married mother of three is simply “jealous that she didn’t snatch me up when she had the chance.” When asked about his past romantic relationships and whether the Plantain could interview his previous girlfriends for this profile, Moskowitz would say only that he had “dated” two women – Jessica and Deborah – in college and has not met any women who were "worthy" of him or his intellect. No last names were provided, however it is noteworthy that Moskowitz’s alleged past girlfriends share names with two of the three women that accused him of sexual assault during the 2008 campaign. The third woman, as listed in the Obama for America memorandum provided to the Plantain, was named "Dory". Ms. Freedman declined to comment on whether she was indeed that third victim.

“I’m interested in starting a relationship,” said Moskowitz. “Sure. But right now I’m just focused on getting Donald Trump elected President.”

SURROUNDED BY STACKS OF DATA, Moskowitz spends nearly all of his time crafting messages designed specifically to appeal to the basest instincts of the American people in order to persuade them into a fear vote in favor of Donald Trump. When asked to apprise his situation, Moskowitz said his job is phenomenal and that he is very well paid, and that the fact that he is in charge of the presumptive Republican nominee's general election strategy is an “incredible accomplishment” and a “testament to [his] own genius.”

It is not difficult to draw parallels between Moskowitz and Trump, or understand why the two men have developed a kinship toward each other. One cannot help but wonder the true effect these two men have had on each other, or the effect of their relationship on the Country. Has Donald, himself an insecure and boisterous man, provided Moskowitz with a role model he needed to fully embrace his own bad behavior in exchange for political power and personal gain? Has Moskowitz provided Donald with the theoretical underpinnings necessary to exploit, as he has done so many times before, average Americans for his own grandiose glory? Have the two conspired to doom American democracy and usher in a new, more divisive political reality? The answer to all these question seems, more and more likely, to be yes.

It really is quite incredible,” admitted Dory Freedman of both her college friend's rise to power and the campaign for which he works. “For better or worse, it’s incredible.”