One More Cross-Country Showdown: 1993 Chrysler New Yorker vs 1993 Cadillac Sixty Special

Good morning! For your Monday edition of the Shitbox Showdown, we have one car from our very own Stephen Walter Gossin, and one anti-car of my choice. They are all the same year, more or less the same class of car, and certainly the same level of comfort.

But first, let’s see Friday’s results. I showed you a little principle EV compliance, and a basic ICE car kit for half the price, to see if you all thought EVs were ready for beat status. The results were mixed: The gas car won, but not by the entire vote. A few of you expressed concern about remaining battery life, and I think that’s the biggest hurdle cheap used EVs will have to overcome. I mean, we can’t all fall back on the big benefits of an electric car with a brand new battery.

As for me, if I lived in Portland, I’d definitely consider an EV or a cheap old PHEV. There are many places to pay, and the distance is short; you can go across town and back and still only travel 40 miles. But I’m moving to rural Maryland in a month, and I don’t think the place that advertises “Cold Beer and Live Bait” has any Level 2 chargers. I’d rather stick with gas for now.

Now, since I have already mentioned my upcoming move, and we will be looking at one of the SWG cars, I can also tell you that we were planning a collaboration for this summer. And not just a collaboration, but a major cross-country adventure in cheap cars that would require nerves of steel, a good sense of humor, and probably many spoonfuls of oil on the side of the road. Because of my argument, unfortunately, it will not succeed. Fear not, however; Stephen and I are still talking about a partnership once I settle down – little by little.

For now, though, let’s just check out Stephen’s latest rescue, and the closest deal I could find for sale in my neck of the woods.

Engine/drive system: 3.3-liter overhead valve V6, four-speed automatic, FWD

Location: Wilmington, NC

Odometer reading: 113,000 miles

Operating mode: It runs and runs well

If this is the car I have in mind, our man Gossin has been working on this for a long time. If memory serves, he found it abandoned in an alley, looked for the owner, and found it with a song. (Maybe literally.) It’s the last year for the K-New Yorker, with a 3.3-liter V6, an “Ultradrive” transmission, and the most comfortable seats you’ll ever see.

Stephen has put a lot of work into this car, both mechanically and cosmetically. It has new brakes, and has just been calibrated and serviced. It also has a new blue top, to match the interior, instead of beige, to match the color. It’s an odd choice, but I think it works. It also has a new title, which is a nice touch. Most vintage cars look great inside – until you look up.

The New Yorker, and its lower sibling in the Dodge Dynasty, looked old-fashioned and powerful next to Ford’s aggressive Taurus and GM’s sleek W-bodies. There’s a reason for this: Lee Iacocca preferred “traditional” designs, with a formal square roofline, so that’s what Chrysler built. It wasn’t until Iacocca announced his retirement that Chrysler designers were free to explore more modern designs, such as this car’s successor, the LH platform.

It’s not perfect, but it’s pretty good, and I trust Stephen won’t let it out of his sight until it’s as mechanically sound as he can make it. Yes, it’s a confused look and probably sticks like a brick supported by a bunch of gummi bears, but if you want excitement, buy a Miata. If you want a comfortable, reliable car that’s gone over with a fine-tooth comb, here it is.

Engine/drive system: 4.9 liter overhead valve V8, four-speed automatic, FWD

Location: Portland, OR

Odometer reading: 68,000 miles

Operating mode: It runs and runs well

Cadillac’s full-size model line was quite controversial in the late 1980s and early ’90s. You had the DeVille, available in both sedan and coupe guises, which was front-wheel drive for the 1985 model year. Then you had the Fleetwood, which was also front-wheel drive, except for the Fleetwood Brougham, which was the old platform of the rear wheel drive, until it dropped the “Fleetwood” from its name in 1987 and simply became the Cadillac Brougham. In 1987, the Fleetwood Sixty Special appeared, as a fancy version of the Fleetwood. Then in 1993, a new rear-wheel drive car took the Fleetwood name, and the Fleetwood Sixty Special also dropped the “Fleetwood” name and became this car: the Cadillac Sixty Special. Did you get all that?

Cadillac wasn’t exactly on the cutting edge of fashion at this time either. This car has a very formal roof, lots of chrome, a landau roof, and very close tailfins. Under the skin, it’s a hell of a lot more sophisticated than its rear-wheel-drive counterparts, with four-wheel independent suspension and a supercharged “HT” V8 driving the front wheels. I know this forum well; I had an ’89 Coupe DeVille for several years. I really liked it, but it got terrible gas mileage and was a bear to work on. Amazingly comfortable, though.

This one only has 68,000 miles on it, and the seller says it runs and drives well, and everything works. It sure looks nice and clean. Leather interior is optional, I believe, and this one is in good shape. One thing to check is the seat belt buckles; on my DeVille, one of them was broken and wouldn’t stick, and I test-drove another Fleetwood sedan from this era that had the same problem. You can replace them with any old GM seat belt buckles, but then they won’t have the Cadillac vein on them.

Outside, its biggest flaw seems to be a couple of wheel center caps. This is also not a typical Cadillac thing – it crashes when the brakes get hot. Until a few weeks ago, I had a spare part from the junkyard hanging on the wall. I tied it up and struggled to keep it while cleaning out the garage, but I threw it away in the end.

I have long thought that “grandfathered” cars like this are one of the best ways to get affordable transportation in good condition. Sure, you have to stop handling, but you get a lot of comfort. One of them I can vouch for mechanically; the other, well, it’s at the dealer, but it looks good. Which one do you choose?

(Image credit: Craigslist sellers)