Richard Chaifetz, a Chicago based billionaire is CEO of ComPsych, and owner of a Major League Pickleball team. In addition a new La Quinta California mansion, the 69-year-old Chaifetz and his wife Jill also own several condos at Chicago’s Trump Tower, a $34 million oceanfront estate in Florida, an apartment at New York City’s venerable 15 Central Park West building, and their main residence — a blufftop mansion in the suburbs of Chicago, among various other property holdings.