Good morning! For your Monday edition of Shitbox Showdown, we’ve got one car from our very own Stephen Walter Gossin, and one car to challenge it chosen by me. Both are the same year, more or less the same class of car, and definitely the same level of comfort.
But first, let’s see Friday’s results. I showed you a basic little compliance EV, and a basic appliance ICE car for half the price, to see whether you all thought EVs were ready for beater status. The results were mixed: The gas-powered car won, but not by a whole lot. Quite a few of you expressed concerns over the battery’s remaining life, and I think that’s the biggest hurdle that cheap used EVs are going to have to overcome. I mean, we can’t all fall ass-backwards into a great deal on an electric car with a brand-new battery.
As for me, if I were staying in Portland, I’d definitely consider an inexpensive older EV or PHEV. There are plenty of places to charge, and distances are short; you can go all the way across town and back and still only travel about 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 out front. I’d better stick with gas for now.
Now, since I’ve already mentioned my impending move, and we’re going to look at one of SWG’s cars, I might as well tell you that we were planning a collaboration for this summer. And not just a collaboration, but an epic cross-country adventure in cheap cars that would require nerves of steel, good senses of humor, and probably way too many roadside greasy spoons. Because of my move, sadly, it isn’t going to work out. Fear not, however; Stephen and I are still talking about a collaboration as soon as I get settled – just a little smaller in scale.
For now, though, let’s just check out Stephen’s latest rescue, and the closest counterpoint to it I could find for sale in my neck of the woods.
1993 Chrysler New Yorker Salon – $4,400
Engine/drivetrain: 3.3 liter overhead valve V6, four-speed automatic, FWD
Location: Wilmington, NC
Odometer reading: 113,000 miles
Operational status: Runs and drives great
If this is the car I’m thinking of, our man Gossin has been working on this one a long time. If memory serves, he found it abandoned in an alley, tracked down the owner, and got it for a song. (Possibly literally.) It’s the final year for the K-based New Yorker, with a 3.3 liter V6, an “Ultradrive” transmission, and the most inviting-looking seats you’re ever likely to see.
Stephen has put a lot of work into this car, both on the mechanical side and the cosmetic side. It has new brakes, and it has just been aligned and had the transmission serviced. It also has a new landau top in blue, to match the interior, instead of beige, to match the paint. It’s an unusual choice, but I think it works. It also has a new headliner, which is a nice touch. Too many old cars look fine on the inside – until you look up.
The New Yorker, and its less-fancy sibling the Dodge Dynasty, looked old-fashioned and stodgy next to Ford’s radical Taurus and GM’s sleek W-bodies. There’s a reason for this: Lee Iacocca preferred “traditional” designs, with a formal squared-off roofline, so that’s what Chrysler built. It wasn’t until Iacocca announced his retirement that Chrysler’s designers were free to explore more modern designs, like this car’s successor, the LH platform.
It isn’t perfect, but it is mighty nice, and I trust Stephen not to let it out of his sight until it’s mechanically as good as he can make it. Yeah, it’s frumpy-looking and it probably handles like a brick supported by a pile of gummi bears, but if you want excitement, buy a Miata. If you want a comfortable, reliable car that’s been gone over with a fine-toothed comb, here it is.
1993 Cadillac Sixty Special – $4,500
Engine/drivetrain: 4.9 liter overhead valve V8, four-speed automatic, FWD
Location: Portland, OR
Odometer reading: 68,000 miles
Operational status: Runs and drives great
Cadillac’s full-size model lineup got downright confusing in the late 1980s and early ’90s. You had the DeVille, available in both Sedan and Coupe forms, which became front-wheel-drive for the 1985 model year. Then you had the Fleetwood, which was also front-wheel-drive, except the Fleetwood Brougham, which was the old rear-wheel-drive platform, 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 over 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 style during this time either. This car has a very formal roofline, lots of chrome, a landau roof, and damn-near tailfins. Under the skin, it’s a hell of a lot more modern than its rear-wheel-drive stablemates, with four-wheel independent suspension and a transverse “HT” V8 driving the front wheels. I know this platform pretty well; I had an ’89 Coupe DeVille for a couple of years. I liked it a lot, but it got awful gas mileage and was a bear to work on. Unbelievably comfortable, though.
This one has only 68,000 miles on it, and the seller says it runs and drives great, and everything works. It sure looks nice and clean. The leather interior is an option, I believe, and this one is in beautiful shape. One thing to check is the seatbelt buckles; on my DeVille, one of them was broken and wouldn’t latch, and I test-drove another Fleetwood sedan of this era that had the same problem. You can replace them with any old GM seatbelt buckles, but then they won’t have the Cadillac crest on them.
Outside, its biggest flaw seems to be a couple of missing wheel center caps. This is also not an uncommon Cadillac thing – they fall off when the brakes get hot. Up until just a couple of weeks ago, I had a spare one from a junkyard hanging on the wall. I hemmed and hawed about keeping it as I was cleaning out the garage, but I threw it out in the end.
I have long thought that “grandpa” cars like these are one of the best ways to get an affordable ride in good shape. Sure, you have to give up some handling, but you gain a whole lot of comfort. One of them I can pretty much vouch for mechanically; the other, well, it’s at a dealership, but it looks good. Which one is your pick?
(Image credits: Craigslist sellers)
I gotta go with he “celebrity provenannce” of the Chrysler. When I sell it for $50k at Barrett-Jackson in 40 years, it will be becauses it was once owned by the legendary SWG.
In all honesty, though, it’s a tough call. I kinda dig ’em both, but it looks like the hood on the Caddy may be pretty sun burned, and that will just bug me, every time I walk up to it.
Besdises, when hunting shitboxes; you are usually better off buying an OK car from a known seller than a maybe OK car?, from an unknown. (even given the low miles on the Caddy). I’m confident that SWG has driven the old K, enough that is is somewhat sorted.
I daily it! It’s Grandma’s living room on wheels.
Thanks for the vote of confidence and kind words my man!
I’d like the warranty of the Chrysler. I mean anything goes wrong post a comment on the site and at the very least you have tech support. But the Inky Black exterior with a blood red interior just screams mafia. Can you imagine pulling up from behind with this beast the theme from the Sopranos playing, dark tint man next best thing to a hearse.
Chrysler all day long. Cheaper to fix a glorified K car than a FWD Cadillac with a v8. Plus the colors of it. And hidden headlamps, and gold and black, classic colors. I preferred the pre facelift squared off version of the New Yorker. I will always love a button tufted velour interior no matter the color or car. Why can’t we have whore house interiors anymore???
I was actually so divided on this one but was leaning towards the Caddy so voted for that. I think it was more difficult on this one since the K car is SWG’s car and would be so awesome to own one of his…but I usually vote based on preferences of make/models and then a variety of factors on each specific car
I’m going with the Caddy. 68k original miles? With a fairly reliable 4.9 Vee Eight? In right decent shape? For $4500? It’s a steal.
The pop ups on the Chrysler are cool but aren’t they sort out of sync with the rest of grandpa’s car?
Just the fact that these two uesteryear holdouts were sold at the same as the LS400 is kind of mind blowing. Wasn’t that New Yorker K car based?
I’m sorry, did none of you see the HIDDEN HEADLIGHTS!?
That plus the provenance gives the win to the New Yorker, and Gossin Motors Backyard Auto Rescue, son!
Thank you! Im genuinely surprised that this group of hidden/pop-up aficionados has not much mentioned them in this comment section until now!
Thank you for carrying that torch for all of us, Geoff.
(also, huge points with this guy for remembering my tag-line, son!)
One has an engine made of glass, the other has a transmission made of glass.
Unlike the early 4100 with their head bolts pulling off the aluminum block, the 4.9 ended up being much more reliable. As long as it was regularly maintained I’d say it’s a safe bet
Yeep, owned a 4.9 eldo, and it lived quite a long trouble free life til i sold it to a stoner who wrapped it around a tree
The 4.9 had not alot to watch for, and the 4.5 was slightly worse, but will go 200k with out much fuss but the rear plugs definitely suck ass to get to.
The 4.9 was the right choice back in the early to mid 90s when the Northstar debuted. Way less powerful but also way more reliable than the later. It doesn’t surprise me GM worked out all the issues on the HT engine just to commit the same mistake over the next decade with their new DOHC engine.
Yeah… irony with the deathstar was a handful of headbolts and mediocre headgaskets.
Such a neat engine.
You’re making me choose between two stunners from the last gasps of the BROUGHAM ERA????? You’re a TERRIBLE PERSON and I appreciate this impossible choice.
I think I’d pick the Caddy, though. I’m a Caddy person. The seats in the New Yorker look FAR more comfortable given my absolute hatred of leather, but a lower-miles Caddy like that is simply a steal and I like the color scheme (read: not beige) way more. We also had an ’89 DeVille when I was a kid and it was a great car! Comfortable, classy, incredible HVAC — everything you’d want in a Cadillac (except cloth seats…bring back cloth seats, Caddy).
Both are good (well, “good”) choices, but I went with the Caddy for prestige alone.
No offense to SWG’s or his Chrysler, but the interior just looks like it smells like cherry-scented air fresheners.
SWG, obvs.
I will walk with my people.
You do know that today is EARTH DAY, right?
Yeah, and they had to move a lot of earth to get the raw materials for these land-yachts.
I voted New Yorker just because I trust SWG wouldn’t knowingly sell an absolutely total crap-can. Can’t say the same for some unknown dealer in Portlandia. If it were two random sellers, I would’ve gone for the Caddy.
Very kind of you, and thanks! It’s true that I can’t keep advertising cars for sale in this small beach town and writing about them here on this site if I was peddling trash. You reap what you sow.
It feels good to hold your head high after a job done the right way. Thanks for the vote!
I gotta vote for the Cadillac if for no other reasons then the color and those rear fender skirts.
But as for the New Yorker, have those rear tail lights been Frenched? If that’s how those rolled off the line, then I want to give some serious points to whomever designed that portion of the car!
Excellent eye and excellent take. It’s one of my favorite design elements (that is nowhere near celebrated enough) on these cars.
Bravo!
That subtle rounding of the front and rear fascias was part of a midcycle refresh for the ’92 model year. I first remember noticing the difference during a trip to Florida (where I believe 90% of these New Yorkers were sold). We were visiting my grandfather, who owned a 1990-ish Dodge Dynasty at the time. Except for the hidden headlights, the more angular 88-91 New Yorker looked pretty much identical to the Dynasty. The rounding seems like a subtle change, but it made those refreshed ’92 New Yorkers instantly recognizable in traffic, puttering along in the right lane on I-4.
It’s SWG’s ChNY. It’s an awful car but it strangely appeals to some part of me that I don’t like to acknowledge. It looks to be in better shape than the Caddy and has Gossin’s label of approval: easiest choice ever.
Your wisdom shines like a beacon of light from Argentina to The Carolina Coast.
Thank you, Sir! I’m actually closer, living in Cental America, so the beacon is more Dynasty than Imperial. But I’m writing an article on ’60s compacts still active (somehow) in Argentine motorsports, so there’s that.
Best of luck with the sale! If I land THAT job, I’d love to have that NY delivered to San Salvador and drive it all the way back to its namesake city.
The lesser of two evils? If I had to choose one of these fright pigs…The New Yorker. Cue Frank Sinatra! But….I spent the same amount of $ couple years ago for an 04 Toyota. It has been one of the best car’s I’ve ever owned. And I’ve gone thru about a 100! Ah the good old days when you could get up early and buy a 60s Mustang..”runs, needs work” for $1000. Bought a 66 and a 68 for $600 each! Shows you what the $ is really worth.
Lots of other choices out there for $4500. Just sayin…but I’ll play the game.
Sinatra bought a K-Car limo in his later years over the usual Lincoln and Caddy offerings. The man was known as the greatest of all time for a reason!
And let’s not forget the Chrysler Imperial Frank Sinatra Edition. Even came with some of music (cassettes) in the glove box! Now you’re stylin’ ….
Isn’t that 4.9L V8 an aluminum block with iron heads? And if it’s a pain to work on, all you have is a downsized, late 80’s Cadillac.
I’d rather rock the New Yorker. I’ll take a chance on the Ultradrive. I can only imagine how many were junked because people used GM fluid in them, and not the correct Mopar ATF+4.
The 4.9 was the last iteration of the HT 4.1 that was introduced in 1981…..and yes that was the iron head and alum block. Like so many GM engines (4.1)…..it was a reliability nightmare at first but then became decently reliable later on.
Excellent choice. Extra points for ATF+4 knowledge. Thanks for the vote!
I’m a Caddy man at heart, but that one’s 68k miles don’t look like they’ve been too kindly to it, and in this case SWG’s recent man-ten-ance (read that in Derek Bieri’s voice) adds some value here, so I’ll go with the fancy K-car today. Surprising myself today!
Heck yes! any <$5K car that has had every mechanical system reviewed and addressed is hotter than an overheating iron blocked, aluminum-headed Cadillac V8.
Thanks for the vote my friend!
Happy to do it!
Oooohhhh, that giant K makes me feel all sorts of funny inside (might be seasickness). If you’re gonna shitbox, go ahead and shitbox to the hilt.
I like your style.
I’ll take the Chrysler. I will definitely trust an Autopian who has put work into this car and can answer mechanically specific questions.
The Caddy isn’t bad but it’s at a dealership so no history or receipts probably. Neither of these cars is my style but I’ll go with the New Yorker and those quilted seats.
Well said and thank you!
The first thing you want with a 31yr old Ultradrive purchase is a receipt with a date and mileage of the most recent ATF+4 service. We have that and much more here.
Quilted seats for the win.
I rate low miles as almost as good as an SWG makeover, and the Cadillac isn’t a glorified K-car, so I’d take the Cadillac with the truly odd name heritage.
That said, if you’re going to get a K-car, this is the singular one to have. Enlarged platform, a decent V6 motor, a comfy interior, and the SWG treatment? These definitely make this K-car more than just simple transportation.
Excellent take. The only car that beats this one in the K-Car Olympics is the ’93 Imperial with the 3.8L V6 and ever more plastic chrome trim.
A silver podium finish is still nothing to sneeze at and it’s not like these cars are on every corner lot these days.
Thanks for the kind words and for the vote!
I can hear the whine of the Ultradrive from here. Hopefully serviced with actual ATF+4 fluid and not Dexron. The latter fluid led to early mortality of many of the already none-too-robust Ultradrives.
Normally, the sheer baroqueness of the New Yorker and it’s late Iacocca-era vibe would pull at the heartstrings in an ironic sense. Suspension of Jell-O? Yup. Landau roof? Check. Whitewall tires? Absolutely. Ride the torque wave? As much as a ’90s-era pushrod V6 can do its big cubic inch V8 of yore impression.
But like Jake from the Blues Brothers, I find myself asking: “Where’s the Cadillac? The Caddy. Where’s the Caddy?”
It is here. I gotta go with the real thing, not the K-car impression thereof. I don’t care if the cigarette lighter works.
You had me @ “Jake.”
Even though you picked the Caddy, your above take on all the greatest aspects of the New Yorker is spot-on.
Putting fresh ATF+4 in this thing was the absolute first order of business after getting it home. The legend of misappropriated fluids in the Ultradrive is fading as they are disappearing from this world, but bravo for bringing that aspect to this comment discussion.
Thanks for the pro-New Yorker sentiment, regardless of your vote.