Politically Presentable:  Jared Kushner and Ivanka Trump attend a benefit for the New York Metropolitan Museum of Art last May.

Donald Trump’s Favorite Son-In-Law Is Jewish — Does That Matter?

On stage at Donald Trump’s victory party on primary night in Manchester, New Hampshire, Trump’s son-in-law Jared Kushner was hard to spot.

A polished Harvard graduate wearing muted grays, Kushner seemed ready to fade into the background alongside Trump’s sons Don Jr. and Eric in their wide, bright ties — but Trump wouldn’t let him.

“And Jared,” Trump said, gesturing past his daughter, and Kushner’s wife, Ivanka Trump. “Jared is a very, very successful real estate entrepreneur in Manhattan. But he likes this better than real estate I think.”

What Jared Kushner likes and doesn’t like is one of the emerging mysteries of Trump’s presidential campaign. A 35-year-old Jewish real estate developer, Kushner was best known, until this year, as the owner of the New York Observer and the son of Charles Kushner, who spent more than a year in federal prison for, among other things, hiring a prostitute to seduce Jared’s uncle, taping their encounter and sending the recording to Jared’s aunt.

Now, after Super Tuesday has shifted Trump’s bid for the Republican presidential nomination to increasingly likely outcome, Kushner is in an unusual position: a privacy-seeking Manhattan Jewish businessman with the country’s most polarizing Republican for a father-in-law. And privacy desires notwithstanding, Trump has not hesitated to use his son-in-law as a live prop.

“Yes. I am a great friend of Israel,” he told Fox News host Sean Hannity at a February 22 town hall meeting in Las Vegas. “I was the Grand Marshal of the Israeli Day Parade… I have so many friends. In fact one of them, one of my great friends—where is Jared, my son-in-law? Where is he? My son-in-law is Jewish, and he’s fantastic — a very successful guy in the New York real estate. So, there is nobody closer.”

An external spokesperson for the Kushner Companies, of which Kushner is CEO, declined to make him available to speak for this story. Friends and colleagues either declined to speak about Kushner or did not respond to requests for comment. But Trump performances like the one in Las Vegas, and Kushner’s appearance in New Hampshire, along with another campaign stop in Iowa in early February, could draw new attention to the Jewish real estate mogul with a troubled family history.

An alumnus of Harvard, where he received his undergraduate degree, and New York University, where he earned graduate degrees in law and business, Kushner is CEO of the Kushner Companies, which owns Manhattan office buildings, a New Jersey mall and tens of thousands of apartments across the country, among other properties. Kushner owns the Observer newspaper, an upscale New York paper. His brother, Joshua Kushner, was an early investor in Instagram and is a co-founder of the health insurance startup Oscar, among other ventures.

Yet Kushner’s place in the Trump clan remains an enigma. Brought up in a modern Orthodox Jewish community in New Jersey, Kushner has given almost exclusively to Democrats, including Hillary Clinton. His father, now a convicted felon, was in the 1990s and early 2000s the largest Democratic political donor in New Jersey. And although his brothers-in-law Don Jr. and Eric Trump are best known for appearing in a set of safari photos with exotic game they shot in 2011 in Zimbabwe, including a cheetah, Ivanka and Jared are smooth urban sophisticates with boldfaced-name friends and heavy-duty business connections.

A fawning Town & Country profile in late 2015 called Ivanka a “modern-day superwoman,” and featured friendly quotes from Roger Ailes of Fox News and Mika Brzezinski of MSNBC, both of whom have been critical of her father. The couple has vacationed with Rupert Murdoch and his ex-wife Wendi Deng, and their daughters were flower girls at the couple’s 2009 wedding.

Trump’s apparent fascination with his daughter has made Ivanka an object of fun. He comments regularly on her looks, and has joked that he would date her if they were not related.

Yet Ivanka and Jared seem to exist in a different sphere than the rest of the Trump family. In glossy photographs in Vogue and on Ivanka Trump’s carefully curated Instagram account, the couple look rich, stylish and, in a decidedly un-Trump-like way, tasteful. “You hear that name, Ivanka, and you expect fur, leather,” Brzezinski said to Town & Country. “But she’s really poised, elegant, down to earth.”

Also separating Ivanka Trump and Jared Kushner from the rest of the Trump family is their religion. Kushner attended the modern Orthodox Frisch School in Paramus, New Jersey, for high school, and Ivanka converted to Judaism under the tutelage of Kehilath Jeshurun spiritual leader Rabbi Haskel Lookstein. (Lookstein declined to comment for this story.) The two have told reporters that they observe the Sabbath with their children on Friday nights.

While it’s hard to picture Kushner and his wife among the garish Trumps, Kushner, arguably, had the best possible preparation for being a Trump. As the son of Charles Kushner, Jared Kushner knows a few things about loose-cannon dads, and about loyalty.

Charles Kushner and Donald Trump resemble each other, to a point. Both grew large real estate empires, and both had a similar urge to see their surname on the sides of buildings. While Trump puts his on towers and hotels and golf courses, Charles Kushner has put his on an Israeli hospital and a New Jersey Jewish day school.

Where the men differ, of course, is in Charles Kushner’s spectacular fall. According to a July 2009 New York Magazine profile, Jared Kushner was interning in the office of Manhattan District Attorney Robert Morgenthau while on summer break from NYU Law School when he learned of his father’s imminent arrest. That soured him on the life of a government prosecutor: “The law is so nuanced,” he told The Real Deal in 2014. “Seeing my father’s situation, I felt what happened was obviously unjust in terms of the way they pursued him. I just never wanted to be on the other side of that and cause pain to the families I was doing that to, whether right or wrong.”

Charles Kushner’s arrest came at the end of a complex tangle of family feuds, federal investigations and civil lawsuits. It nearly coincided with the 2004 resignation of New Jersey Governor Jim McGreevey, who had close links to Charles Kushner. The New Jersey developer was not just the governor’s largest political donor; he was the former employer of McGreevey’s male lover, whose threatened lawsuit against McGreevey precipitated his resignation.

Charles Kushner was among the largest political players in New Jersey, handing out huge donations through a multiplicity of entities controlled by his firm. He gave mostly to Democrats such as McGreevey and New Jersey Senator Jon Corzine, among others. Charles Kushner’s tax record and political giving came under scrutiny from New Jersey’s current governor, Chris Christie, who was the U.S. Attorney for New Jersey at the time (and who recently suspended his own campaign to be the Republican presidential nominee). Charles Kushner’s sister and brother-in-law cooperated with investigators. Kushner, in response, set up a honey trap, sending a prostitute to seduce his brother-in-law, recording their encounter and sending it to his sister.

The judge in the case called Kushner’s behavior “horrific,” according to a March 2005 report in The New York Times.

Jared visited him in prison in Alabama every week. Later, after his father was released, Jared continued to defend him in the press.

“His siblings stole every piece of paper from his office, and they took it to the government,” he told New York Magazine in 2009. “All he did was put the tape together and send it. Was it the right thing to do? At the end of the day, it was a function of saying ‘You’re trying to make my life miserable? Well, I’m doing the same.’”

Years later, in a 2015 interview with The New York Times, Jared said that the “No. 1 thing” his father had taught him was to “treat everyone with respect,” which seems an unusual lesson to take from a guy who paid a prostitute $10,000 to seduce his brother-in-law.

Charles Kushner has been out of prison since 2006, and has continued his life more or less where he left off. Though Jared now runs the family firm, Charles and his wife, Seryl, remain active philanthropists. Their foundation, on the board of which Jared also sits, gave away $2.4 million in the 2013 fiscal year, much of it to Jewish charities. Charles and Seryl Kushner pledged $18 million to Shaare Zedek Medical Center in Israel in 2014; a hospital campus was dedicated in their name in early 2015.

Since the 2009 Kushner-Trump nuptials, the two families appear to have tied knots beyond the purely social: Last year, Seryl Kushner gave $100,000 to a pro-Trump super PAC called Make America Great Again. (That super PAC closed soon after and gave back some of the money it raised, though Seryl Kushner’s donation does not appear to have been returned.)

Jared Kushner has been suspected of helping the Trumps in other ways, too. A February 2014 article in Jared Kushner’s New York Observer attacked New York State Attorney General Eric Schneideman, outlining what it called a “pattern of political opportunism in which enemies pay while friends skate.” At the time, Schneiderman was pursuing a case against Trump University, a Donald Trump venture that Schneiderman accused of fraud. The Observer story condemned Schneiderman’s case, saying that the decision to pursue it was “fraught with odd ethical choices.” Months before the Observer article was printed, in response to another magazine’s report on the Schneiderman investigation, Donald Trump had tweeted that an unnamed publication was “doing a story on me to get even.”

Press coverage of the Observer story speculated immediately about the newspaper’s motives. Though the Observer story had run with a disclaimer noting Kushner’s relationship to Trump, an article in The New York Times published soon after referred to “suspicions that the article was ordered up as retribution on Mr. Schneiderman.” The Observer’s editor, Ken Kurson, strongly denied the claims.

The Observer has been cautious throughout the Trump run, printing disclaimers at the bottom of every news story that mentions Trump.

For now, that’s the only daily reminder of Jared Kushner’s oblique role in the Trump universe. Whether the Jewish son-in-law of the Republican front-runner can retain that distance as the Trump campaign rolls on remains to be seen.

Contact Josh Nathan-Kazis at nathankazis@forward.com or on Twitter, @Joshnathankazis

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