Until 2014, a post war car hadn't even won best of show in the past 55 years.
This is the 1954 Ferrari 375 MM Scaglietti Coupe of Jon Shirley, who won best of show in 2008, and he was once president of Microsoft, and remained on the board of directors until 2008. This Ferrari was designed by Sergio Scaglietti for Roberto Rossellini who comissioned it for his wife, Ingrid Bergman. It’s one of only five roadgoing versions of this racer, and was the first passenger Ferrari to be bodied by Scgalietti.
Info and image found in Sept 1st 2014 issue of Auto Week magazine, photo by Kimball Studios, courtesy of Pebble Beach Concours, and http://www.starkinsider.com/2014/08/concours-delegance-1954-ferrari-375-named-best-show-complete-list-winners.html