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Low-Mile Driver: 1959 Cadillac Fleetwood

Automotive styling tends to evolve, and many trends will go in and out of fashion numerous times over the years. Bodies will be square and angular. They will then become softer and more rounded before heading back towards the angular once again. The styling trend that disappeared, never to return, was the fin. The end of the 1950s saw these reach their peak, and nowhere were they more pronounced than on the offerings from Cadillac. This 1959 Fleetwood is a perfect example, and it is looking for a new home. It is no trailer queen. This is an original survivor that is ready to be driven and appreciated. Located in Carmel, Indiana, you will find the Fleetwood listed for sale here on eBay. The owner has set the BIN at $24,500, although the option is available to make an offer.

You don’t necessarily need to be a classic car enthusiast to recognize a ’59 Cadillac. Those enormous fins and bullet tail-lights are an automotive icon and represent fins at their most outrageous. They are the feature that easily dominates the styling of this car. When you look past them at the vehicle’s overall condition, what you find seems to be quite promising. The owner claims that there is no rust under the Fleetwood, with the floors and frame structurally sound. There are also no signs of any rust in the panels, which is a good starting point when assessing this classic. The owner acknowledges that the Dover White paint isn’t original, with the car receiving a repaint at least 15-years-ago. It isn’t perfect, but it looks fine for a driver-quality survivor. The panels are straight, and all of the tinted glass looks to be in good condition. The ’59 Cadillac brought plenty of “bling” to the table. This was used to accentuate the fins, so it is essential that the chrome and those incredible tail-lights remain in good condition. Once again, the news is positive, and while the chrome isn’t flawless, there are no problems that would justify immediate restoration or replacement.

The interior trim of a ’59 Cadillac was luxurious when new, but they can tend to age rather badly. Upholstery is prone to deterioration, and the dash can look tired very easily. This interior isn’t perfect, but it is a lot better than some that we have seen here at Barn Finds. The worst issue is the headliner, which looks dirty and stained. I suspect that it may have deteriorated beyond the point of no return. There are no rips or tears, so it wouldn’t require immediate replacement. If the buyer does choose to replace it, then they might be in for a pleasant surprise. It is not hard to find a replacement in the correct material and stitching for under $350. Who says that prestige brands need to be outrageously expensive? The majority of the upholstery looks to be in good condition, although there is a tear on the outside of the front seat on the driver’s side. A competent upholsterer should be able to apply a blind patch, so a new cover won’t be necessary. The front seat is power operated, but this is one of the few features that doesn’t work. The clock can be added to the list, but the remaining gauges, power windows, and the radio all work as they should.

The Cadillac is a numbers-matching car and features a 390ci V8, a 4-speed Hydramatic transmission, power steering, and power brakes. The seller is the vehicle’s second owner and claims that it has a genuine 55,000 miles on the clock. However, he doesn’t indicate whether he holds evidence that can confirm this. The Fleetwood doesn’t get a lot of use these days, so the tires have become dry and cracked. The owner states that these will need to be replaced. A new fuel tank has recently been installed, along with new plugs, plug wires, thermostat, and upper and lower radiator hoses. Add in a rebuild for the carburetor, and you now have a classic that drives nicely. These are a car designed to isolate you from the hustle and bustle of the outside world. They are big and bulky, so it’s impressive to consider that if you gave this one enough room, it would be capable of wafting along at 120mph.

A 1959 Cadillac Fleetwood is not going to suit every enthusiast, but these are a car that has a surprisingly strong following. Even though fins died at the start of the 1960s, there are still plenty of people who would love nothing more than to park a car like this in their driveway. The simple fact is that even if the motoring public started demanding the return of fins tomorrow, it will almost certainly never happen. Vehicle safety requirements are tighter now than they have been at any time in our history. They would never allow a manufacturer to produce a car like this.. So, if you have a rebellious streak, but like to live life in the lap of luxury, maybe your limo has arrived.


  1. Rex Kahrs Rex Kahrs Member

    Seems like a really nice iconic Caddie for the money. Personally I would not take an open title though; it would need to be a clear title from the person I bought the car from.

    Like 3
  2. Howard A Member

    These always remind me of Elvis, although, I don’t think he had a ’59 4 door. The other day, I happened to see a white ’62 4 door like this at a local shop. When I looked inside, the mileage said 2600 miles! And it looked like it. When I asked about it, the mechanic said, he bought the car brand new, and NEVER left town, so it does happen.

    Like 8
  3. Mitchell Gildea Member

    Only car more iconic than this one is a same-year drop top. To be fair tho, I almost would prefer this model

    Like 3
    • Jonathan

      Agreed. I’d rather have the fixed roof versus a convertible.

      This was the local bank president’s car and his wife had the convertible….if I were to make up a plausible backstory for this care.

      Like 3
  4. Bob C.

    Back in the 90s, my former landlord had a white 59 convertible sitting under a bunch of stuff in her horse barn. She thought the longer she held onto it, the more money she would get. Probably still has it.

    Like 1
  5. Norman McGill

    I was 16 in 1959 and this was the epitome of a luxury car. The Lincoln was a bit longer and the Imperial was a bit wider but nothing said “success” like the 59 Cadillac and especially the Fleetwood. Jet planes were a brand new thing along with TV and the rotary lawn mower a few years earlier. The F-86 swept wing Saber Jet was very exciting and the new cars tried to mimic that look.Those were the Super Car years to me and I’m grateful to have lived when they were alive and new rolling along the highway. This car is a rare find indeed. Now if I could just win the lottery. Ha!

    Like 7
  6. JoeNYWF64

    Not sure why many cars of the ’50s place the battery in FRONT of the radiator support. I would think a/c would be very common in Caddy’s by 1959 – none here.

    Like 0
    • Chuck Dickinson

      AC WAS becoming more common, esp. on luxury cars, but it was still a very expensive (compared to other options) proposition, so unless you lived in extreme conditions (humidity/heat), you might think twice about spending the money for it. I was involved with the restoration of many (at least 15-20) 59/60 Cads back in the 80s/90s–they were nearly all Pacific NW cars, and AC was not common on even luxury cars here at that time. Only a couple of them had AC, one being a 60 Eldo. Even the 59 & 60 FWs were, like this one, loaded, but ‘airless’.

      Like 1
      • Norman McGill

        AC was first offered by Cadillac (I think) in 1941. A friend has a ’41 sedan with AC that works really well. So here we are in the late fifties and AC hasn’t really made much headway probably because ,as you say, the expense involved and where you lived. I paid extra ($800?) for AC in a ’64 Pontiac LeMans convertible I bought new here in Florida but subsequent new cars all had air in them as standard.Now it’s almost impossible to find any car without it at least down here. I do remember my fathers ’48 Packard sedan with no air. It was like riding in an oven in the summer and that was in Massachusetts. Now it’s hard to imagine getting along without it.

        Like 0
  7. John

    Having spent a lot of weekends detailing a 59 Cadillac, my eyes sense work has been done on the front and rear quarters, could be the quality of the pictures, the lines aren’t right and filler should be looked for. Still, I’d buy it, it’s not a bad price for what you’re getting if there’s at least some metal below the trim line, not just filler. The restoration costs for these cars will outpace the value pretty quickly on all but the Biarritz, but they’re a great car and if you plan to hold onto it because you love it, do it up the right way and enjoy something we’ll never see the likes of again

    Like 0
  8. Bob Mck

    I have a 59 Sedan and would be proud to park this one in my garage. It needs a horn ring which will cost $1200. But I think a deep detailing would bring her back to fabulous.

    Like 1

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