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The Chrysler Windsor

Chrysler introduced the Windsor line of vehicles in 1939, and manufactured the line on and off over the next two decades. The Windsor was a full-size offering from Chrysler that was initially positioned above Chrysler’s entry-level Royal, which eventually took over Chrysler’s highest price crown in 1951.

Upon its introduction, the Windsor was Chrysler’s slightly smaller option to its larger New Yorker model. It was offered in long and short wheelbase options that seated anywhere from six to eight passengers.

The 1941 option for the Windsor introduced a new station wagon style vehicle, named the Windsor Town and Country. This model was designed by the president of Chrysler, David A. Wallace, himself. This new Windsor model was an early version of what would become the modern station wagon, moving away from the boxier, wood versions of the past. For collectors, the pluses on the 1941 Windsor Town & Country include:

  • The potential for appreciation
  • A uniquely styled body due to its new design at the time

Conversely, the minuses for collectors of the 1941 Windsor Town & Country are:

  • Scarcity of the model
  • Extremely hard to maintain the wood structure

Production of the Windsor line temporarily shut down due to war production efforts.

Post-War

The end of the war brought the Windsor back into production for Chrysler. In its reintroduction in 1946, the Windsor was very similar to the 1942 version, the last pre-war model. Chrysler welcomed the return of the Windsor with open arms as the model made up roughly 63% of their sales.

In 1949, Chrysler celebrated its 25th anniversary and redesigned many of its active models, including the Windsors. The new design included a boxier body than many of the competitors’ comparable models. This model also featured the introduction of a dashboard that was padded with sponge rubber for driver and passenger safety.

As the decade moved on, Chrysler made few changes to its now lowest priced Windsor. Small changes included a new, standard, electric clock and optional, electric windows in 1951 and standard power brakes in 1952. As 1954 came along, Chrysler once again began rolling back the Windsor’s production, shelving all versions of the model, except for the Windsor DeLuxe.

Looking Forward

Chrysler’s $300 million redesign of its lineup of vehicles in 1956 meant design changes were in store for the Windsor as well. The result was a Windsor model that featured the first tail fins on a Chrysler. For the most part, the interior of the newly redesigned Windsor’s stayed the same, however, a new Highway Hi-Fi phonograph player was added as an option for the first time.

The 1957 model year once again brought another redesign for the Windsor. This time the tail fins were extended up higher and vertical tail lights were added. The 1957 model year was not kind to Chrysler vehicles as they suffered through issues with product quality when torsion bar suspensions began to break and the vehicles began to rust. 1958 brought the introduction of the “Auto-Pilot” system option available in all Chrysler cars, including the Windsor.

After the 1958 model year Chrysler shelved the Windsor domestically, and only sold the model in Canada and other countries.