This is what I believe to be a 1954 Chrysler Windsor. It was photographed at the Bombers United Car Club show in Silicon Valley in 2011 at Kelley Park.
Although not a car expert, I think it's one of those years because it has a single curved windshield and because the basic Windsor model was dropped, leaving only the Windsor DeLuxe, which also had a new grille.
"The Chrysler Windsor is a full-size car which was built by Chrysler from 1939 through to the 1960s," according to Wikipedia. "The final Chrysler Windsor sold in the United States was produced in 1961, but production in Canada continued until 1966. The Canadian 1961 to 1966 Windsor model was for all intents and purposes the equivalent of the Chrysler Newport in the United States.
"The Windsor was positioned above the entry-level Royal from 1939 to 1950. With the demise of the Royal for the 1951 model year the Windsor became Chrysler's price leader through to 1960. For the 1961 model year the Chrysler Newport was made the marque's price leader with the Windsor positioned one level above the Newport. Chrysler replaced the Windsor name in 1962 with the introduction of the non-lettered series Chrysler 300."
Keywords:1954 Chrysler Windsor DeLuxe, Bombers United Car Show, Glenn Franco Simmons, Kelley Park, San Jose, Silicon Valley