First Son-in-Law Jared Kushner had a mixed record in New York managing the Kushner family’s real estate portfolio. His purchase of 666 Fifth Avenue (yes, that was the address), the family’s biggest investment and at $1.8 billion the most expensive deal in U.S. history for a single office tower, proved epically ill-timed.

Mr. Kushner bought that unlucky address in 2007 just months before the Great Recession threw the N.Y. market into a historic tail spin. It took a billion-dollar bailout in 2018 from an asset management firm, its primary owner the Qatari government, to interrupt what had been the Kushner family’s near ruin.