On Tuesday, New York magazine published an essay by a 24-year-old law student who recently paddleboarded around Manhattan for the first time. “I signed up for the race because I thought it sounded cool,” writes our participant. “Of course, when I asked around, everyone said it was really hard and I’d better start training.” The smugness, the entitlement, the painfully obvious observation — one might wonder: Who cares? Until you look at the byline and realize: Oh, of course. Another Kennedy foisted upon us. Our diarist is none other than Jack Schlossberg, grandson of JFK, son of Caroline, accomplishment-free save...