If you want to understand Jared Kushner, I recommend starting with the dimples. When Jared smiles, his dimples do the work, cleaving his supple cheeks in an unconvincing approximation of contentment. The giveaway isn’t merely that his lips don’t seem to lift properly at the corners but that his eyes dissent. You can learn to force a smile, but getting your eyes to play along is a trickier thing. And Jared’s eyes, flanked by crow’s feet that seem strangely out of place on his otherwise unlined face, are so wounded and tender, a volatile mixture of rage and oceanic hurt, that it can feel somehow indecent to really look at them.
My study of Jared’s face is part of a long-standing effort to figure him out. For six eventful months back in 2012 — long before his carefully calibrated demeanor was drawing comparisons to “a haunted doll” and “an early Westworld robot,” and before the mysteries behind that subdued grimace became one of the key preoccupations of intelligence services around the world — my career depended on the answer.
I first encountered Jared in 2010, when I went to work for the New York Observer, the weekly Manhattan newspaper he’d purchased a few years before, reportedly as part of a crisis PR plan to rebuild his family’s reputation. The young prince of a prominent New Jersey real estate family, Jared was just 29 at the time. He looked even younger, despite the grown-up responsibilities that had been thrust upon him in the wake of a family scandal. In 2005, Jared’s father, the developer and Democratic power broker Charles Kushner, had been sentenced to 16 months in federal prison after being convicted of 18 felony counts of tax fraud, election violations, and witness tampering. The latter charges were the most damaging: Convinced that his family members were cooperating with a government investigation, Charlie had hired a prostitute to seduce his brother-in-law, secretly videotaped the encounter, and sent the footage to his sister as a warning and as revenge.
Seeking to turn the page, Jared had helped engineer the $1.8 billion purchase of the office tower at 666 Fifth Ave., the most expensive deal for a single property in the country at the…