On a cold afternoon in late January, I pulled into an industrial side-street of Saint Petersburg. There, I met with a man who I’ll refer to as “Oleg.” Oleg drives a 1996 Jeep Grand Cherokee ZJ—an “Orvis Edition” with a 5.2-liter V8. As we stood chatting by the hood of his car, many heads turned, and a fair share of strangers offered their thumbs up. A few others asked if the car was for sale, to which Oleg responded, ominously: “takiye mashini ne prodayutsya” (“cars like this don’t go up for sale”). In America, the Grand Cherokee ZJ is at...