Work In Progress: 1959 Chrysler Windsor Convertible

In the pantheon of ChryCo head stylist Virgil Exner’s over-the-top designs, today’s find of a 1959 Chrysler Windsor, courtesy of T.J., is pretty tame by comparison. Sure, it has memorable tailfins, which many automotive designs possessed in ’59, but the oddball trapezoidal angles, diagonal headlight pods, and zig-zagging stainless trim are, fortunately, missing.  Not that this resident of Woodinville, Washington is a shrinking wallflower, no, not at all, but it does carry a refined and more contained bearing than some of Mr. Exner’s creations exhibit. And, being a convertible, this is a rare one, so let’s examine it further.

Things come in threes and that’s how Chrysler rolled in ’59 with the New Yorker at the top of the heap, the Saratoga in the rocking chair, and the Windsor bringing up the markers. Windsor’s were available in two and four-door hardtops, a four-door sedan and station wagon, and a convertible such as our subject car. As for rarity, the Windsor convertible only mustered 961 copies in ’59. The top dog New Yorker came in drop-top form too but its numbers were weaker still with only 286 units seeing the light of day.

The seller claims, “selling a 1959 Chrysler Windsor convertible in running and driving condition…I found this car in a boneyard some years ago and saved it…original black car with white conv. top and factory white leather interior…” Further added is, “body is pretty good with some minor rust, dings and dents…underside is solid and body is mostly original paint.” There’s no doubt about it, this Windsor shows fantastically though a boneyard existence while still maintaining its mostly original paint seems incompatible. But then maybe the seller’s definition of a boneyard and mine are considerably different. While the finish is deep, the body appears to be rust and damage free, the chrome and stainless shines, this is a fair weather car only, it has no folding top or mechanism.

Originally powered by a 305 gross HP 383 CI V8, the born-with powerplant has been swapped for a 413 V8 that originally took up residence in a ’59 New Yorker. The seller tells us that this one runs and drives but offers no additional details regarding its operating prowess. As is usually the case with this era Mopar, a push button activated TorqueFlite automatic transmission handles gear changes.

The white leather interior with its front swivel seats is, as the title suggests, a work in progress. The rear seat bottom and upholstery panels are MIA as are all four window regulators and the glass that they regulate – kinda puts this convertible into cabriolet territory. Fortunately, all of the dash gauges, including the clock and radio work. The seller makes mention of a gasoline fueled heater that is included in the sale – I’ve not heard of that option and some how, in my mind anyway, it’s not a confidence inspiring way to heat one’s car.

The upside here? The seller has put a lot of effort into rejuvenating this rare convertible, and the engine upgrade is a solid plus. There’s even a ’59 New Yorker parts car included in the sale! The downside? It’s missing a lot of stuff. Considering this Chrysler’s current state, I’m on the fence regarding the ask. It’s available here on craigslist for $20,000. What do you think, priced right or not quite?