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Car of the Week: 1958 Chrysler Saratoga

I lived in Fall River, Mass. in 1991. While running an errand, I drove past a used car dealership that had a really cool-looking ‘50s car in the front row. I did not know what it was until I got up close and checked it out. It was a 1958 Chrysler Saratoga four-door hardtop.
Car of the Week 2020

By Ken Biello

I lived in Fall River, Mass., in 1991. While running an errand, I drove past a used car dealership that had a really cool-looking ‘50s car in the front row. I did not know what it was until I got up close and checked it out. It was a 1958 Chrysler Saratoga four-door hardtop. I'm not sure what caught my eyes first; the color combo, or the sweeping fins. Either way, I knew I wanted it, four doors and all.

After starting the car, by way of the push-button drive, I heard the wonderful sound of a classic, American V-8 motor! Running through factory dual exhausts, the engine was smooth and revved powerfully. I took the car for a test drive, and was amazed at the looks this vehicle was getting, and all the "thumbs up" from other motorists. I drove the car back to the dealer and we sealed the deal. I came back the next day to collect my new baby.

Since I did not have a garage to store and work on the Saratoga, I kept it at my in-law’s garage. Each week, as time and funding permitted, I went to work on the car. The gas tank had a leak, the carburetor needed to be rebuilt, the transmission was weeping fluid, the brakes were soft, etc. It was all about time and money, neither of which I had!


Fast-forward to the spring of 1994. Not enough time, money or space, a house that needed work, and family time being more important, and I made the decision to sell the Saratoga. I contacted the dealer that I had purchased the car from in 1991, and he agreed to purchase the car back. I also took a 1981 F100 pickup truck with the trade, as I needed one for the home repairs I was neck deep in. The only photos I had really ever taken were probably in the first few months that I had the car.

I mourned selling the car, but I did what I felt I needed to do. But I had my pictures!

Labor Day weekend, 2014. I took my son Jacob and my daughter Mya to a local speedway thrill show on August 31. Maybe an hour into the event, a man and his young son sat down next to me, to my left. We are all watching the spectator drags, truck enduros and other races, and I hear this man talking to his son. The voice sounds familiar, but I cannot place it. A few minutes later, and it dawns on me; this is the auto dealer that I had bought my Saratoga from in 1991! During a brief intermission of the show, I lean over and told the man "About 20 years ago, I bought an old Chrysler from a guy in Fall River that would blow away half of the cars on that track". The man replied: "I have an old Chrysler". I say back to him "Is it a 1958?" He replies back "Yes, it is". I say back to him "Is it a 1958 Chrysler Saratoga?" He looked at me in bewilderment, and said, "How did you know that?" I replied, "Because I bought it off of you in 1991, and sold it back to you in 1994". He could not believe the coincidence, and neither could I! Of all the places he and his boy could have sat, he was sitting right next to me. This speedway must be able to hold at least 5,000 people. A coincidence indeed!

ken-saratoga-1991 001

We got to talking about cars, and I asked him "Whatever did you do with that car?" He said that he still had it, and hadn't driven it in over 20 years! Shortly after I sold the car back to him, he tucked it away in a garage that he had just recently purchased, closed the door, and never opened the door again. I could not believe it! I asked if it would be for sale, and he said that he would consider it. I reminded him that he had not driven the car in over 20 years, and maybe it was time to hand it off. I went to see the car at his storage garage, and when he opened the door, I knew immediately it was my old car. It looked like it was in a time capsule. Four flat tires and 20 years of dust, but everything was as it was in 1994. Even the change that I had in the ashtray was still there, leftovers from the local hamburger drive-thru! We negotiated a deal, and a week later I had the car on a flatbed hauler on the way to my home. When I was handed the keys, they were on the keychain that I had bought in 1991. Even the title was still in my name, from 1991!

A complete and almost eerie note; when I originally bought the Saratoga, it was on Aug. 31, 1991. When I ran into the dealer at the speedway that I bought the car from, it was on Aug. 31, 2014. What are the odds?


My daughter helped me wash off the years of dust, dirt and grime when I got the car home. Surprisingly, the paint was still in great shape. Sitting for so long, nearly every mechanical component will need to be refurbished or replaced. I'm going through it all, step by step.

The car is a numbers-matching, 354 poly, cast iron push-button Torqueflight beauty. The only options ordered were power steering, power brakes, power front bench seat, power antenna, and two-tone color spear. The other option, and a rare one I'm told, is the Model 801/803 gas hot air heater. I have never seen one before, nor have I ever seen one on another car before. I intend to get all of this in working order. The specifications for that 354 poly engine are 310-hp, with 405 ft.-lbs. of torque. Pretty respectable for such a heavy car.


I still cannot believe how I got this car back. All the stars were aligned I suppose. My mom calls this phenomenon a "God wink". I have since taken no less than 100 photos of this Saratoga. At this point in my life, I have a garage, with a space that is just right for the Saratoga to sleep in. A little more time now, a little more money now, and with my "new" baby back, the fun begins once again!



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