As an elementary-school kid in suburban New Jersey, Jordan Roth says he didn’t quite grasp the dizzying extent of his family’s wealth, though he got a tart first clue as a 6-year-old, when a classmate opened his birthday gift and proclaimed, “Humph. I thought I’d get a bigger present from you.” His family had a live-in housekeeper, but that wasn’t especially unusual in Ridgewood; more unusual was the family driver, but because Roth started attending Horace Mann at age 10, he was less self-conscious about this amenity than he might have been, as a fair number of the students got dropped off each day by someone, rather than taking a bus. It wasn’t until he was a teenager and moved to a marquee address on Park Avenue that larger disparities began to reveal themselves. His father, for example, had a private jet. “During the holidays, people would ask things like, ‘What flight are you on?’” says Roth. “How do you answer that?”
