Chrysler Windsor 1940 images

This 1940 Chrysler Windsor coupe pairs a rare prewar Fluid Drive transmission with a full cosmetic restoration. See what the photos confirm about its color and body style, and why so few genuine examples from this cut-short production run survive today.

The Windsor was introduced in 1939 and continuously produced until 1942 when the war interrupted all manufacturing.Â After a 3 year hiatus production continued for the Chrysler Windsor until 1961 in the USA and until 1966 in Canada.

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The fluid drive was introduced by ChryslerÂ in 1939. The feature is added to a factory equipped three speed standard transmission with a conventional clutch, but in addition, a hydraulic coupling is also present. The coupling performs the same as the flywheel; in succeeding years a modern style torque converter will be used in the hydraulic couplings place. The fluid drive allows the operator to leave the carÂ in first gear, the vehicle stopped, Â without activating the clutch peddle. The engine can remain idling, at a stop, in 1st gear similar to an automatic, but the transmission must be shifted the same as a traditional three speed. The 250.6 CID – L-head six engine can maintain an idle, stopped, in Â high gear, then brought to driving speed like an automatic, although sluggishly. For the best performance Â the transmission will have to be shifted.

MCF thanks Gateway Classic Cars for images provided here.

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Picture a Detroit showroom floor in the fall of 1939, where a freshly redesigned six-cylinder Chrysler sat under a grille nobody had seen before, and a hidden transmission trick let a driver forget the clutch pedal at every stoplight. Chrysler called it Fluid Drive, and it promised something close to automatic-shifting comfort arriving almost the exact same year Oldsmobile’s genuinely clutch-free Hydra-Matic reached the market — not years ahead of it, as it’s sometimes given credit for. The Windsor wearing that technology wasn’t the flagship of the lineup – it sat modestly below the New Yorker and Crown Imperial – yet it quietly carried some of Chrysler’s most forward-thinking engineering into everyday driveways. Barely two years into its run, world events would freeze this generation of Windsor in time, cutting production cold before the car could fully prove itself. So what exactly made Fluid Drive different from a real automatic, and why did Chrysler make buyers wait three years to find out if it was worth it?

The Transmission That Wasn’t Quite Automatic

Fluid Drive paired a hydraulic coupling with a completely conventional three-speed manual transmission and clutch pedal. The coupling let the engine keep spinning at idle while the car sat stopped in first gear, without the driver touching the clutch at all, and the car could even be brought up to speed from a stop in that gear alone, if sluggishly. For real performance, though, the driver still had to work the shifter through the gears just like any other manual – Fluid Drive smoothed things out, but it wasn’t yet the true automatic transmission it was often mistaken for.

A Redesign Interrupted by War

1940 brought a full styling overhaul across the Chrysler lineup, including a new horizontal grille and sealed-beam headlights – an industry-wide innovation that year. The Windsor was offered on two wheelbases, 122.5 and 139.5 inches, priced from roughly $935 to $1,350 depending on body style, and helped push Chrysler to one of its stronger prewar sales years, though exact factory-wide production tallies for 1940 vary by source. Production continued only through 1942, when World War II halted the entire industry’s civilian output. When Chrysler resumed building cars after the war, the Windsor nameplate came back and stuck around remarkably long for a car that started so modestly – all the way through 1961 in the United States and 1966 in Canada.

Why Prewar Survivors Are Getting Harder to Find

Prewar Chrysler production was a fraction of what the postwar boom would bring, and daily use, wartime scrap drives, and decades of neglect thinned the surviving population further. Convertible coupes like the one pictured here, sourced through Gateway Classic Cars, represent an increasingly scarce slice of American automotive history from just before everything changed.

What the Photos Actually Show

These consignment photos show a fixed-roof coupe body, not a convertible despite what a few of the older image captions on this gallery claim, finished in a deep, dark navy that reads nearly black under showroom lighting. The horizontal-bar chrome grille and vertical bumper guards give the front end real presence, and the interior carries a cream-colored steering wheel with a wide horn ring, matching cream dash trim, and a simple push-button style radio faceplate typical of the era. The overall condition, straight chrome, unblemished paint, clean glass, is consistent with a car that has been through a proper restoration rather than one running on decades of untouched originality.

Owning a Prewar Chrysler Today

A 1940 Windsor built to this standard is not a car most owners drive daily; parts sourcing for a prewar L-head six and its Fluid Drive hydraulic coupling is a specialty pursuit today, handled by a small number of shops and enthusiast networks rather than any general parts store. That scarcity cuts both ways for value: genuinely correct, well-documented prewar Chryslers draw serious interest at auction specifically because so few remain in condition good enough to show, while incorrect or heavily modified examples struggle to find the same audience.

Where the Windsor Sat in Chrysler’s 1940 Lineup

Below the Windsor, Chrysler offered the entry-level Royal on the same general platform; above it sat the New Yorker and the limousine-grade Crown Imperial, both offering more standard equipment and, in the Crown Imperial’s case, a straight-eight engine rather than the Windsor’s six. That positioning made the Windsor Chrysler’s value performer of the range, a car that carried real engineering, Fluid Drive included, without the New Yorker’s added cost, which is likely part of why it sold well enough to justify bringing the nameplate back after the war and keeping it in production for another two decades.

That long production run, spanning three very different design eras from the streamlined prewar body seen here through Chrysler’s finned 1960s styling, is unusual for any American nameplate and is a large part of why enthusiasts specifically collecting Windsors have such a wide range of body styles to choose from.

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