Until recently, the most controversial members of Chicago’s ultra-rich and powerful Pritzker family were the billionaire Illinois Gov. J.B. Pritzker — a longtime Democratic activist and bail reform advocate — and his billionaire transgender cousin Jennifer, who’s funneled millions into universities, medical schools, gender clinics and nonprofits in support of “gender-affirming” medical care. This week, however, they’ve been overshadowed by family members who are embroiled in two of the biggest news stories of the moment. The governor’s sister Penny, 64, is front and center with the resignation Tuesday of Harvard president Claudine Gay over multiple instances of plagiarism. Penny has...