While Forward Look Chrysler fans may dream of finding a 300B in a barn, or perhaps a New Yorker St. Regis hardtop, it was the base Windsor that did the heavy lifting at the company that Walter P. founded. Out of 128,322 Chryslers manufactured for 1956, a full 53,119 of them were Windsor Sedans such as the one shown above, which Barn Finder T.J. found here on Marketplace in Boise, Idaho, with an asking price of $9,999. I’ve always felt that the 1955-56 Chrysler products were the link between Virgil Exner’s Italianate concepts of the early 1950s and the wildly finned creations he later became best known for. It’s the perfect balance, and according to the selling dealer, this one has had just two owners.
The 1955 Windsor had a 331-cubic-inch Chrysler V8, but for those of who you might have “Hemi” on your mind, this is not it; rather, it’s the 225-horsepower “Poly” engine that Chrysler called the “Spitfire.” While the TorqueFlite became an option partway through the model year, this one appears to have the two-speed PowerFlite automatic (based on what I can see of the pushbutton shift controls on the dashboard). The selling dealer says that the mileage is original at 76,231, and that the Windsor “runs and drives good.” It has a Champion aluminum radiator, which might not look exactly right under the hood of a Forward Look Chrysler, but in my experience, it will cool the engine reliably. The giant fan shroud should keep the engine temperature under control at an idle, too.
The car is being presented as all-original, but the seats have, at the very least, been reupholstered. No harm, no foul…it would be asking a lot for any seat cover to stand up to 70 years without someone giving it the side eye. The Chrysler has power steering, power brakes, and even a working power seat, something you may expect to see in a top-shelf New Yorker rather than a comparatively humble Windsor.
The undercarriage looks solid, although there is some rust on the driver’s side front fender. Dual exhausts are always a welcome touch, and if the differential has the standard gear, it has a 3.73:1 ratio, not bad for getting two tons of Chrysler moving down the road.
There are a few dents and creases on the passenger side, but all-in-all, this big Mopar sedan is nothing the new owner will be ashamed of: It has room for the whole crew, a strong V8, and some of the best fins to come out of Detroit. While you might want to fix that fender rust and install a new set of wide whites, this Windsor is basically ready to cruise as-is. And when it’s time to park, you can sit in a lawn chair and simply look at those fins.








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