1959 Chrysler Windsor Convertible Is a 1-of-1 Gem, but There’s a Catch

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The Chrysler Corporation rolled out some of its finest vehicles in the 1950s. From the Chrysler 300 “letter series” to the Plymouth Fury and the Dodge Coronet, the big-fin Mopars of the mid-to-late-1950s will steal the show at any classic car event today.

But these nameplates are the ones that usually grab all the attention on the classic car market. Chrysler’s divisions produced more than a dozen of cool-looking rigs back in the day. The Windsor, for instance, is one of those classics that doesn’t get as much love as it deserves.

Sure, it wasn’t as fancy as the New Yorker, and it wasn’t offered with the brawny 392-cubic-inch (6.4-liter) V8 of the 300 “letter series,” but it featured the same fabulous design penned by Virgil Exner in the late 1950s. What’s more, the series spawned a few extremely rare versions. The 1959 Windsor Convertible, for instance, was built in just 961 units, which makes it a hard-to-find classic.

And as this potentially unique example in Gray Rose Poly shows, it can be quite spectacular in the right color combo. Why potentially unique, you ask? Well, the seller claims it’s one of only 10 surviving 1959 Windsors and the only one in this light purple hue. But there’s a catch.

His conclusion is not based on factory records or an official report. It’s the result of a registry that he and other 1959 Chrysler Windsor owners put together. Now I’m not challenging their finds, but with close to 1,000 units built back in 1959, chances are there are more than 10 survivors out there.

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Of course, most of them are probably rotting away in junkyards and barns, but I’m pretty sure a few unrestored and restored examples that still run are “flying” under the Windsor fan-club radar.

Nevertheless, Gray Rose Poly wasn’t a very popular hue back in the day, so this particular example may be a 1-of-1 gem. Especially if we factor in the Mauve vinyl/Times Square cloth upholstery, which is gorgeous if you ask me, and factory power steering, brakes, swivel seat, and windows.

But regardless of how many cars like this are out there, this Windsor has to be the finest example of its kind. Restored to perfection in 2007-2008, this Mopar shines like new, and it’s a numbers-matching classic front to rear. And yes, it still features its factory 383-cubic-inch (6.3-liter) Golden Lion V8, a not-so-common “tall-deck” mill similar to the more iconic Wedge unit.

This Windsor Convertible is located in Lubbock, Texas, and the seller wants to let it go for $97,500. Granted, it’s a lot of cash for a 1959 Chrysler that’s not a New Yorker or a 300, but eBay seller “caprockclassics” is entertaining offers. Would you spend the summer in this Mopar?

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