On a recent episode of “Jay Leno’s Garage,” appraiser Donald Osborne challenged Leno to guess which of three unrestored classics had appreciated the most — and even Leno got it wrong. The reveal says a lot about how collectors actually value originality over polish, a lesson echoed by Ralph Lauren’s own decades of collecting and by the crowds still showing up to events like the Daytona Turkey Run. Read on to see why the roughest-looking car in the lineup won.