[Photo:  Todd Heisler / NYTimes]

The Strange, Complex Education of Jared Kushner; can the political neophyte, who has stumbled in publishing and real estate, recognize his own limits - in the White House?

Earlier this year, as his family’s namesake company prepared to partner on a $340 million deal for 733,000 square feet of real estate in downtown Brooklyn, Jared Kushner sounded amazed by the prospect. It wasn’t the dollar figure or the scope of the project. It was the locus. Brooklyn, despite being decades into its evolution from outer borough province to gentrification-on-steroids case study - replete with destination restaurants, gussied-up shuffleboard studios, multiple SoulCycle locations, overpriced condos, Girls, and an obsessively competitive private-school scene - appeared to still be something of a mystery to the 35-year-old real-estate executive and newspaper publisher. “I’ve been checking out my brother’s company and tech companies and people really seem to love Brooklyn,” he told a real-estate acquaintance, in disbelief. “They live there!”

Kushner’s surprise is bewildering. Not only did the young executive live across the river with his wife, Ivanka Trump, and their 3 children; not only was he in a business aligned entirely with Brooklyn’s growing fortunes; but his own successful company had also invested in a nearby building some 3 years earlier, to the tune of another $375 million.

“My impression wasn’t that he was a moron,” this real-estate acquaintance continued. “But he thought he was so much smarter than he was. That makes for really dangerous and decisive decisions. He is really confident that he’s doing the right thing, but he has no idea what he’s doing.”

Kushner, of course, has not had to endure a long and grinding ascent throughout his career.

• He matriculated to Harvard shortly after his father, real-estate magnate Charles Kushner, made a $2.5 million gift.
• Shortly after graduation from a joint law and business degree at NYU, he rose to the the family real-estate throne as a principle at Kushner Companies during his father's well-documented stint in federal prison.
• At the same time, he purchased the The New York Observer for $10 million and installed himself as publisher.
• Not long after the Observer purchase, near the peak of the real-estate bubble, Kushner Companies paid $1.8 billion to acquire 666 Fifth Avenue, a 41-story, embossed aluminum-clad office building across from Rockefeller Center.

The deal was staggering, even amid a frothy climate, both for its price and structure. The Kushners paid 3 times what the building had sold for less than a decade earlier in a debt-filled deal. A story in The NYTimes noted that “some real-estate specialists regard the 666 Fifth Avenue transaction as a textbook example of the risky practices that were prevalent before the current credit squeeze.” Years later, the paper would note that the deal was “so highly leveraged that the cash flow from rents amounted to only 65% of the debt service.” At the time, Kushner responded to the story by saying, “The good news about our capital structure is that the loan is in place till 2019, and we have over $100 million that we can spend. We’ve put ourselves in a position where we can be competitive to attract tenants.”

Kushner, the scion of a billionaire, has a history of jumping into situations with little experience, making risky calls, and coming out fine on the other end.

• The Observer, which no longer publishes in print, and hardly wields the influence it used to, is still kicking around.
• The Fifth Avenue deal, despite costing a fortune, is offset by the portfolio of his mammoth family organization.
• His foray into politics is yet another example. Indeed, his father-in-law Donald Trump may have run the most chaotic, hate-filled, disorganized campaign in modern American history, but Kushner is likely emboldened by his role in it. Without any previous political experience, he has been credited with masterminding Trump’s digital operation and prompting key hirings and firings, appointments and demotions.
• His mug appeared on the December cover of Forbes under the bold type face: “This guy got Trump elected.”
• He is reportedly weighing whether or not he will take on a formal role in the White House. A source told me that the couple is also strongly considering a move to D.C.

Meanwhile, those who knew Kushner during these formative years wonder if he will make the same mistakes of inexperience and hubris on a far more significant scale. According to a number of people who spoke under the condition of anonymity, out of a desire to keep ties with him or professional obligation, Kushner is a kind, charming, mild-mannered guy who has long been overmatched. But he has been buttressed from failure by his rich, well-known family. As he prepares to take on a role with global significance, what happens when the parachute of his family’s wealth can no longer brace the fall?

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