When I was getting ready to leave for college in the fall of 1966, my parents decided that I needed a better car than the sort of ratty 1956 Pontiac I had been driving. My dad and I went down to the used car lot associated with the local General Motors dealer. On the back row were two nice looking cars, each with about 50,000 miles and in our price range of about $500, which is about $5,000 in 2024 dollars.
The beautiful one was a red 1957 Cadillac Coupe Deville. The one next to it was a gray 1958 Oldsmobile Super 88. I loved the Cadillac, but my dad insisted that the maintenance on the Oldsmobile would be a lot less, so we bought the ’58 Olds.
The irony turned out to be that the Oldsmobile was the most unreliable car I ever owned. Hardly a month passed without a major repair expense. After about a year we traded it for a 1959 Oldsmobile which was immediately T-boned by a student who ran a red light. I took the insurance check myself and bought a 1961 Chrysler New Yorker which was one of the best cars I ever had. After that experience, I felt confident to make my own decisions about what cars I would drive; I am sure my dad was happy about that.
I still wish I had bought the red Cadillac. Now a 1958 Oldsmobile is worth about $25,000 and a red ’57 Coupe Deville is worth about $125,000. Of course, I would have sold it within a few years and would have been kicking myself each time I’d think of it.
Someone once commented to race car driver Denise McCluggage, that if she still had all of the cars she had owned, she would be rich. Her response was that it was the other way around. If she had been rich, she would still own all of those cars. She sold them because she needed the money to buy something else.
I was thinking about that ’57 Coupe Deville because Jay Leno featured his 1957 Cadillac Coupe Deville in his weekly YouTube show, “Jay Leno’s Garage.” His car is unmodified and totally stock. He marveled at how nice it drove and that it had plenty of power even by modern standards.
In 1957, the automotive journalist, Tom McCahill, tested the major luxury cars that year and declared the Cadillac the winner, beating even the prestigious European makes, Rolls Royce, Mercedes Benz, and Jaguar of that year. He even marveled at the surprising fuel economy.
If I had the space and money to be a car collector, I would have in my collection a red ’57 Coupe Deville and a black 1961 Chrysler New Yorker, or probably a 300G. These cars represent the best from that period and will always have a special place in my memory.