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Playing to Win

Exclusive interview by Yisroel Besser, New York

Just three months ago, as the presidential primary season got underway, the burning question was whether Donald Trump could capitalize on his popularity in the polls and translate that into votes. Ten million votes and victories in 25 states later, the real estate mogul and television celebrity is on the verge of closing the biggest deal he has ever bargained for. An exclusive Mishpacha interview

Wednesday, May 04, 2016

 Mishpacha image

BIG PLANS Donald Trump is curious about what people in the Orthodox world (“not an alien species”) think of him and his ideas, happy to clue Mishpacha’s reporter into plans “that will be beautiful”

I t’s the day before the New York State primary — a race Donald J. Trump is expected to win being that this is his home state, and a race that has turned into a must-win if Trump is to regain momentum after three consecutive losses in Wisconsin, North Dakota, and Utah.

We’re in the hallway outside his office on the 26th floor of the 68-story Trump Tower on Fifth Avenue, three blocks southeast of Central Park. Trump stands waiting for the elevator that will take him down to the lobby for an appearance before the National Diversity Coalition for Trump, whose supporters hail from more than a dozen racial and ethnic groups, including African-Americans, Hispanics, Asian-Americans, Jews, and Muslims.

Trump is the tallest man in the elevator going down, and also the most talkative.

An aide informs him about a new endorsement that’s just come in, and the Republican front-runner makes a note to call his newest supporter and say thank you. He jokes with another aide about having added weight to his six-foot-two-inch frame along the campaign trail. When the elevator stops at the second floor mezzanine, where Starbucks is located, Trump tells a colleague: “That’s the best use of the space we’ve ever had, the first tenant that’s really doing well there. Starbucks, what a great company,” he adds, obviously having changed his tune from last December, when he suggested he might terminate Starbucks’s lease after the company announced a change in the color scheme of their traditional, holiday season green-and-red cups.

He’s still talking as the doors slide open to reveal a mass of gawking, cheering, frenzied supporters.

Even though Donald Trump appears exuberant wherever he is in this city of crowded sidewalks, with street vendors hawking wares ranging from hot dogs to T-shirts to cell phone chargers, the acclaim and the passion here in his own tower visibly energizes him. Working the crowd of supporters gathered in the lobby, he’s enjoying himself immensely, foreshadowing something he will express a few minutes later. The greatest attribute he brings to the table as a politician, he will tell me, is a genuine love of people, an interest in connecting with them and understanding them.

Reflections from the flashbulbs make the bronze elevator doors behind him glow like fire. They open to escort him back upstairs, and he waves one last time.

“What a great bunch of people,” he says, brimming with satisfaction, eager for the others to feel what he did. “You can feel the love, right? Right?”

The Jokes Will Stop

Clearly, it’s important to Trump that people like him. I observed him in the elevator and lobby, saw his eager interaction with people, the bonhomie of a small-town mayor walking Main Street.

It’s ironic that his latest endeavor — his quest to become president of the United States — has created quite the opposite effect.

Ever since Trump announced his improbable candidacy last June 16 — two days after his 69th birthday — he has inspired many loyalists, and alienated just as many antagonists. His campaign has earned him friends and adherents, but it has also made him into a target. No Trump comment, it seems, goes unreported. An army of so-called “Trumpets” and the opposing “Never Trump” or “Dump Trump” forces pounce with equal zeal.

His face, his hair, his gestures and mannerisms are a windfall for comedians and political pundits who find Trump-bashing as easy as hitting a baseball off a stationary tee.

Trump has fed the frenzy by teeing off against his many opponents, whether it’s “Lying Ted Cruz” or “Crooked Hillary” or “Little Marco,” but when the sharp edge of the barbed tongue boomerangs to slap him in the face, he concedes that it isn’t easy.

“It hurts,” he admits. “No one likes when people say not nice things about them, but I try not to let it get to me.”

The candidate says he understands the backlash, the anger that’s been directed his way and the deep-rooted cynicism that drives the jokes. “I believe I can help these people, and when I get that opportunity, the jokes will stop,” he tells me. “I try to focus on that.”

With nearly 1,000 delegates of the 1,237 he needs to secure the Republican nomination for president (Trump only needs to win some 40 percent of the remaining delegates to reach the mandatory 1,237) the nearly yearlong quest of this real estate mogul and reality television star to represent his party in the run for the nation’s highest office is in clear sight.

To ensure he gets over the top, Trump has recently shaken up the campaign internally. In the last month, he’s hired two seasoned veterans: Paul Manafort, who has worked for four US presidents, to serve as his delegate process and convention manager in a race that may not be decided until all the delegates are tallied on the convention floor in Cleveland on July 20; as well as a new political director, Rick Wiley, who worked with the George W. Bush reelection team in 2004.

The recent appointments reportedly did not sit well with the campaign team that got Trump this far, but supporters dismiss talk of dissension as “hiccups in the back office” of a campaign that is a new line of business for the boss.

One longstanding Trump employee who asked not to be identified said that the Trump organization “is a well-oiled machine.”

“On the business end, everyone knows their role, and we’ve all been doing our jobs forever, but political campaigns tend to be cobbled together on the fly. Pieces get picked up in motion, so what you’re seeing there is an anomaly.”

Trump is often accused of making claims that cannot be substantiated. At the same time, the facts on the ground seem to demonstrate a real talent for tapping the support of the masses. While hardly scientific data, sentiment around the office bears out his assertion that he’s connected with the people. Employees I spoke with freely, regardless of rank, have been around for years, sometimes decades. One woman told me, “It isn’t just loyalty, it’s also comfort. We feel taken care of.”

The calm atmosphere in Trump’s office — especially in contrast to the commotion downstairs — would seem to corroborate the employee’s account.

The only indication that these rooms headquarter a political campaign and not just a real estate empire are the Secret Service agents quietly going about their business. The men and women at desks and cubicles work quietly, laughing among themselves, going over spreadsheets, and sipping Diet Coke, as in any other office.

The corner office is far less ostentatious than you might imagine.

Trump’s desk features stacks of magazines featuring his famous image on their covers. The walls covered in plaques pay tribute to his generosity. Strangely, many of them are from Jewish causes. (Perhaps not so strangely, considering we invented the fundraising industry.) There is also a gun mounted on the wall, and a collection of pictures. Mainly of himself.

My host — around here, the boss — is downright gracious. Donald J. Trump asks about the magazine, our community, our circulation. He is curious what people in the Orthodox community think about him and his ideas. He is eager for me to understand that Orthodox Jews aren’t an alien species to him, something he’s read or heard about, but people he’s worked with all his life.

The Donald has fed the Trump-bashing frenzy by teeing off against opponents like “Lying Ted Cruz,” but concedes that “no one likes when people say not nice things about them”

Predictably, he tells me about his daughter, Ivanka, who underwent an Orthodox conversion to Judaism, and how Ivanka’s husband — his son-in-law, Jared Kushner — is familiar with Mishpacha magazine.

“So I told Jared, ‘Look, I’ve made the cover of Time magazine four times, maybe I’ll even be on the cover of Mishpacha!’ ” he tells me, laughing at his own difficulty in pronouncing the word.

“It means family, right? Family,” he beams.

He can afford to beam. Even his fiercest opponents have a hard time impugning his family. Trump has five children from his three marriages and is proud of their unique, even remarkable, accomplishments in American public life — namely that children who’ve come from such celebrity and wealth have emerged as hardworking, courteous adults. All three married Trump children — Donald Jr., Eric, and Ivanka — work in the offices one floor down and are in near-constant contact with him.

Do Something Bigger

When we finally sit down to talk “tachlis,” I open the discussion with a touchy question. Donald Trump likes to talk about how rich he is — very rich, very often. In theory, people who do that tend to be insufferable, most likely to be left standing alone at a cocktail party.

Yet this unabashed one-percenter has connected with and earned the trust of the truckers and shippers, the clerks and cashiers who make up middle-class America. He may have the Republican establishment squirming, trying valiantly to adapt to the idea of the New York businessman at the top of the GOP, but he’s certainly hit a responsive chord with voters.

According to the 2016 RAND Presidential Election Panel Survey, a substantial proportion of GOP primary voters hold relatively liberal positions. RAND says Trump has won 45 percent of the GOP vote among those who favor raising taxes for people earning more than $200,000 a year.

How can a person announce their own privilege so vocally and still be one of the boys?

Trump seems to appreciate the question, even with the inherent slight alongside the compliment.

“Look, I built buildings, and I worked with the banks and architects and designers. But I also worked with the actual builders, got to know the guys out there on the site, got to feel their concerns. I’m not them, but I identify with them. I want to make things better for them.”

Trump has proposed revision of income tax brackets that would appear to be beneficial to the Orthodox Jewish community, with its high share of growing low-income families. His plan calls for a 0 percent income tax on individuals earning less than $25,000 a year and married couples earning less than $50,000, a potential boon for kollel and chinuch families. Trump has explained that he would pay for these cuts by eliminating the loopholes made available for the very rich (with which he is admittedly familiar), and special interests.

While lower taxes has always been a Republican prescription for economic growth, critics of the plan contend a 0 percent tax rate carries risks for low-income families, as it incentivizes the comfort of remaining beneath the poverty level, and reducing the incentive to climb out of the hole. It’s a challenge generally issued to Democratic candidates. In this case, Trump, the Republican, answers it, but more like a businessman than a politician.

“Every American is trying to make it. Everyone wants to have a better life. The problem is that they don’t have any money in their pockets. There is nothing to invest, no spare change to put in the stock market or real estate. It all goes to rent or mortgage payments or groceries. By giving them this tax break, we’re putting money in their pockets, and then,” he leans forward, gripping the table, “and then they’ll want to do something bigger. It’s a nation of entrepreneurs. I met the people and they all have dreams.”

And because he’s Donald Trump, he breezily adds, “And by the way, why is it such a hassle to pay income tax? So many papers. Why are poor Americans forced to go pay H&R Block to help them get through the pile of rules and fine print? Let’s make it easy. One form. We’ve figured out how to use technology to make life simpler in so many other areas. Paying income tax shouldn’t be the task Americans dread most. So that’s not a fiscal plan, but it’s part of the way we’ll upgrade the process. We’re going to reduce and simplify and it’ll be beautiful.”

I’ll Do Better

As powerful a position as the presidency is, and while its impact is generally felt closer to home than abroad, Trump has promised to make the world a safer place, and that includes for Jews as well.

In January of this year, Trump was the subject of caustic headlines when he referred to Brussels as a danger zone. “Donald Trump Finds New City to Insult,” wrote the New York Times, ever ready to highlight the candidate’s lack of diplomatic experience. Two months later, after the horrific Brussels airport attack, they swallowed the sarcasm.

On Jewish affairs, Trump turns to Jason Greenblatt, his trusted confidant and chief legal officer of the Trump Organization. The Orthodox attorney is more economical with words than his boss, speaking in a measured voice. “America sets the tone,” Greenblatt says. “We’ll create a different tone in Europe and around the world. We should be creating a culture that strengthens Israel and by extension, individual Jews, Jewish communities. We can do that.”

Visibly Jewish travelers have experienced the subtle change in the airports of Europe, the hostile looks that are no longer veiled.

“Look, you’re a visibly Orthodox Jew,” Trump says, looking straight at me and raising a finger in a trademark gesture. “They see you. They’ve already learned that they can do whatever they want and get away with it. Obama taught them that.”

Trump switches to a more comfortable position and turns schmoozy, drawing a page out of his AIPAC speech. “I don’t get why the Jewish community supports Obama, or why they like Hillary — I really don’t. Maybe it’s out of habit. Honestly? I think he likes Iran better than he likes Israel.”

Trump does this thing with his face where he laughs but also frowns, so that it’s clear that he isn’t joking when he says, “I think Obama has made Iran powerful and rich, and weakened Israel that way. It’s dangerous.

“I believe,” he adds, “that a US president who makes it clear that we respect our friend, and that being aggressive with Israel is being aggressive with us, sends a message with a ripple effect. Across the globe they’ll get the memo: You can’t away with it.”

With less than 24 hours to go before the New York primary, Donald Trump’s time is more precious than ever. New York, with 99 delegates, offers the fourth richest delegate prize in the nation, behind California, Texas, and Florida. Trump won all of Florida’s 99 delegates, lost in Ted Cruz’s home state of Texas, and has his eye on the big prize — California’s 172 delegates — on the final primary day on June 7. He looks forward to each state as a new opportunity.

“I’ve traveled through most of this country in the last few months and met all sorts of people. I didn’t realize how great the average American is. We have the best people out there. We need to ‘make America great again,’ to let those people be great. And on a global scale, it means that we have to start playing like winners. We have all the good cards, but no politician who knows how to use those cards.”

The press has caught on to the narrative of two Donald Trump’s — “The Donald” versus “Donald Trump” — one brash and at times offensive, the second, a backstage figure who is far smarter and affable. The candidate wraps up our 20-minute conversation in full graciousness mode.

I had already prepared a note for Trump to sign, a nice gesture for a friend to whom I thought it would mean a lot. The frontrunner takes the paper and asks a few questions: Why for this guy? What are his challenges and how is he addressing them? Why would the signature mean something? He fires a few more questions, genuinely interested, and then crumples up the paper.

“I’ll do better,” he turns to find a piece of his own stationery — From the desk of Donald J. Trump at the top — writing a new note of his own, thoughtfully crafting an appropriate message.

He shakes my hand and frowns slightly. “How do you think we’ll do tomorrow?”

And without waiting for my answer, he says, almost to himself, “We’re going to win, we’re going to win. It’ll be great.”



Until about a month ago, Jason Dov Greenblatt was the chief legal officer and executive vice president of the Trump Organization, a bright, mild-mannered Orthodox Jewish lawyer from Teaneck. Part of his boss’s inner circle, he’d long represented the author of the Art of the Deal when it came to making deals.

“Jason understands Donald’s thought process, how he approaches an issue, and he’s accomplished great things for the Trump Organization that way,” an industry insider tells me.

Still, the knock on his office door came as a surprise for Greenblatt. “Donald wants you,” said the messenger, and Greenblatt hurried to the conference room, where his boss was meeting a delegation of Orthodox Jewish media representatives.

Less than ten seconds after coming in, the boss had deflected a question on Israeli settlements to his lawyer, and suddenly, Greenblatt was thrust onto the stage.

Jason Greenblatt has no background in diplomacy or politics. He’s never been part of a think tank or study center on Israel, but the man tabbed by Trump as his special advisor on Israel — even as he continues in his legal role for the company — brings something else to the table: real passion for the country.

The Queens native spent a year in yeshivah in Israel before returning home to graduate from Yeshiva University. After a stint with a prestigious law firm, he was hired by the Trump Organization, where he’s remained for close to 20 years.

Both he and his wife Naomi, a psychiatrist, work long hours, but they’ve found a shared hobby. The Greenblatts try to travel abroad with their six children each year, more often than not, to Israel.

Their experiences formed the basis of a book. Israel for Families is a comprehensive and thorough guide, filled with necessary information (insurance, car rentals, routes, schedules, and the like) as well as the inner core — the “why’s” of the trip, the significance and meaning of the various sites. Written in collaboration with the six Greenblatt children, the tone is easy, light, and throbbing with love of the Land.

It seems like quite the project for a couple with full-time jobs — but Jason has experience.

In the early ’90’s, the Manhattan kosher restaurant scene seemed to be in constant transition, with restaurants opening and closing, and hechsherim removed from glass windows days after they’d been affixed. At the same time, the borough was fast becoming the hub of Jewish single life, and a comprehensive list of kosher restaurants was necessary.

In those pre-Internet days, there was a single resource. Jason Dov’s List, as it was known, was photocopied again and again, the authoritative directory of eateries — hechsherim, addresses, menus — passed around shuls and offices. It was the perfect contribution from someone with a sharp eye for detail and a devotion to the wider community. (At the bottom of the list was a suggestion that those who’d benefitted might consider donating money to Chabad in Salt Lake City, since Jason, an avid skier, had come to appreciate the shaliach there.)

Greenblatt has none of the hard-nosed lawyer air. He’s soft spoken and courteous, passionate about his family, committed to Yiddishkeit. And very loyal to his boss.

He’s never yet had to choose between them. “Several times, over the years, I’ve had to walk away from deals because of Shabbos or Yom Tov and Mr. Trump has always been understanding. I remember sheepishly telling him that I had to go home in the midst of intense negotiations over a billion dollar deal. We’d been working for weeks and I’d actually slept in the office for a few nights, but here I was, leaving — for a three-day Yom Tov! I was scared to tell Mr. Trump, but I finally summoned up the courage. He looked at me and said, ‘Jason, go home, be with your family, pray, enjoy. We’ll pick it up after the holiday.’ ”

Jason is gracious about sharing his experiences as a Shabbos observer at the highest level of corporate life, speaking for Chabad, NCSY, shuls, and on college campuses about what Shabbos does for him and his family.

He might be a supreme mensch, but can someone with virtually no foreign policy experience be an advisor on foreign policy?

“Sometimes, too much experience is as bad as too little experience.” Greenblatt reflects. “You can’t conduct negotiations with preconceived notions, locked into a vision of the way things have to be, with no willingness to rethink positions. Sometimes, fresh faces are a good thing.”

He is also confident that his boss will surround himself by qualified people when the time comes to make decisions. “The image people have of Mr. Trump is that he operates alone, listening to no one. It’s not true. He’s great at identifying talent and ability and he hires well. I won’t tell you he doesn’t have his own mind, but he certainly doesn’t micromanage. He finds the right balance.

“Look, when it comes to Israel, Mr. Trump will take the approach he knows best. He’ll try to make a deal.”

And when it comes to deals, there are few people that the candidate trusts more than Jason Dov Greenblatt.

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