Introduced in 1939 and built until 1961 (with a break during WWII), the Chrysler Windsor is a primarily forgotten nameplate nowadays. And that's a shame because it's a cool and more affordable alternative to the fancier New Yorker and 300 "letter series" models.
The Windsor debuted in 1939 as a more upscale version of the Royal. The full-size was very similar to the New Yorkers in terms of equipment, but it came with an inline-six engine under the hood. The range-topping New Yorker, on the other hand, was powered by a straight-eight in the 1940s.
Discontinued in 1942 when the US entered WWII, the Windsor returned in 1946 and was redesigned in 1949. It shared design cues with the all-new Chrysler Imperial but continued to use a six-cylinder mill, which it shared with DeSoto, Dodge, and Plymouth automobiles.
In 1955, all Chrysler were completely restyled by Virgil Exner. The Windsor got the sexy "Forward Look" design language in 1956. The redesign also saw the Windsor receive its very first V8, the 300-cubic-inch (4.9-liter) Poly.
Two more redesigns followed in 1957 and 1959, keeping the Windsor in line with the Town & Country and the iconic 300 "letter series." The Poly unit was replaced by a 354-cubic-inch (5.8-liter) Spitfire in 1957 and a 383-cubic-inch (6.3-liter) Wedge V8 in 1959.
The Windsor went into the history books at the end of 1961 when Chrysler rolled out the 300 non-letter series. Similar in appearance to the much rarer 300G, the final-year Windsor moved 17,336 units. The two-door hardtop is arguably the rarest, with only 2,941 cars made, but the four-door hardtop is also a hard-to-find classic, at 4,156 examples produced. Especially since most Windsors are currently rotting away in junkyards.
The black land yacht you see here is one of those very lucky Windsors that soldiered on through 2023 in one piece. And I'm not talking about a labor-of-love-type restoration. This 1961 Windsor is a full-fledged survivor with original paint and an unrestored interior.
Moreover, it still rocks a numbers-matching 383 V8 under the hood. Sure, the engine bay may have gotten a refresh at some point, but that's a mandatory operation if you want to keep a half-century-old classic running and driving. Even if it has only 22,467 miles (36,157 km) on the odometer.
Overall, it's a genuinely fascinating car. And even though it may not be as fancy, powerful, and desirable as a 300G, this Windsor is pretty close in just about every department. It flaunts the same striking design, has a nice and classy color combo, and the Wedge V8 is no slouch at 305 horsepower (the 300G's 413-cubic-inch / 6.8-liter Golden Lion was rated 400 horses). And at around $20,000 to $30,000 in Excellent condition, the Windsor is quite the affordable classic.
This black beauty is not for sale, but you can check it out in the video below.
Ask Ciprian about cars and he'll reveal an obsession with classics and an annoyance with modern design cues. Read his articles and you'll understand why his ideal SUV is the 1969 Chevrolet K5 Blazer. Full profile
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