The 1940s Chrysler product portfolio offered a near-perfect aspirational ladder for would-be buyers, from the Royal to the Imperial – all aptly named. The Windsor was introduced in 1939, a top-level trim option sitting above the Royal in its “junior” six-cylinder line-up. While not as swanky as the eight-cylinder, longer wheelbase Saratoga/New Yorker models or the majestic Imperial, the Windsor gave buyers a lavish list of options and features, many in common with the “senior” line. The pristine 1941 Windsor convertible featured here is available on craigslist, with an asking price of $27,500. It’s located in Auburn, California. We have Zappenduster to thank, once again, for an excellent tip!
In 1941, Chrysler was touting its Superfinish engine components, requiring very little in the way of break-in mileage. Hiding beneath that hood is a 242 cu. in. “superfinished” flat-head six cylinder making about 112 hp. Also considered worthy of marketing spend was Chrysler’s Fluid Drive semiautomatic transmission: the company advertised the Fluid Drive option rigorously, both in print and via badging on its cars. This example benefits from a long roster of recent work including a rebuilt carburetor and fuel pump, and new fuel lines. The clutch and throw out bearing have been replaced, and the brakes are new top to bottom. The underside is about as good as it gets without a total restoration. The odometer reads 41,000 miles.
The interior is plush, showing off fresh carpet and handsome moleskin upholstery. Chrysler changed its steering wheel to a two-spoke configuration, enhancing visibility of the instruments. Conveniently, this new design provided another advertising platform to remind drivers of its Fluid Drive transmission. The seller notes that every component on the car works, from the heater and lights to the radio and power top. Only said convertible top might require attention, with a few small, but repaired tears.
The paint is lustrous, and though not everyone will agree with me, I like the wide white walls. The styling retains vestiges of the ill-fated but influential Chrysler Airflow – one of the first production cars designed using a wind tunnel. And despite its seemingly high waistline, the Windsor also represents the start of a trend to “lower, wider” bodies that reached an apex in the ’50s. As nice as this example is, 1940s cars have become a tough sell, even convertibles. Yes, there are exceptions – “barrel back” Town & Countrys, senior Packards, European coach built cars – but junior models are suffering. This natty ’41 Windsor Highlander convertible barely breached $20k and failed to sell. Our subject car is beyond reproach, but still might struggle to find a buyer at the current price.








Just think for minute , if you will, some Hollywood big shot bought their kid a brand new Chrysler ragtop. Laid out over $1400 new, that doesn’t sound like much, but almost twice the cost of a Plymouth. Blissfully unaware of what lie ahead, and it was anchors aweigh for junior, leaving the Chrysler behind. Did junior ever come back? Not likely, and here you go. Someone spiffed up a real clean survivor to begin with.
Perhaps you are unfamiliar with old Joe Kennedy’s boys Jack and Joe Jr. Jack received injuries that condemned him to a life of torturous pain. Joe Jr. died having volunteered for an extraordinarily dangerous mission piloting a flying bomb. Both were born with silver spoons in their mouths. had the cars, the cash, and the women. But don’t ever imagine they didn’t pay their dues.
Hang in for another four years.
The horror, somebody successful once bought an expensive car. So you create a story out of thin air to deal with childhood issues.
Steve R
Curt, how much longer until you change your user name? Your getting to the point where you can’t keep your hatred for those more successful that you in check. Will you create a new account on your own or will it get to the point where the moderators delete your account again?
Steve R
This vehicle was born to roam the bucolic, horsey-farm white picket fence outlands.
…and flip-flops do it a grave injustice.
WOW, now this is a car. And for that price, insane. Stop for a second. California car. I hope. so no rust or crap like that. paint looks great, interior looks like a comfy sofa, 6cyl easy to keep running. And a real head turner. So, go try and find any car with 40K miles on it that even comes close to this. This would make a great driver car, it will never be a dream car, but one heck of a car about town. Like I said, all you can find these days at that price is either a used honda. zzzzzzzzzzzz, or a new? A New?
I agree WoodyBoater, 40’s cars offer exceptional value and a driving experience like no other. And yet a wonderful example like this one will sell for so little. Sad.
“Also considered worthy of marketing spend was Chrysler’s Fluid Drive semiautomatic transmission….”
Strictly speaking, Fluid Drive was not a transmission — it was a fluid coupling that replaced the flywheel. The semiautomatic transmission (called Vacamatic in ’41) was optional and paired with the Fluid Drive (also optional). IOW, you could have Fluid Drive without the semiautomatic transmission though they were often paired in Chryslers.
This is a great-looking car. I have a soft spot for these ’40s Chryslers as our family car in the ’50s was a ’48 Windsor Traveler with the Fluid Drive and semiautomatic (possibly standard equipment on Chryslers by then).
Another marvelous Mopar for me to drool over. I really like the color scheme. As Michelle points out; the interest in this era of automobiles is receding as the folks who remember them from their youth age. If you purchase this at anywhere near the ask you are practically guaranteed to be immediately upside down. And when it’s time for it to change caretakers again; there will be even fewer interested buyers. Time waits for no one. GLWTS
So true.
I bought a 41 coupe that I’m hot rodding. The poor gal was so ugly, I remade a whole new front clip similar to a 40 Willys.
Even with BBC 496, OD tranny, GV behind that, IRS, the works, she’ll never be worth more than 30K.
Ya, with demand so low for these, I do not feel bad at all for cutting it up.
http://www.spiuserforum.com/index.php?threads/1941-chrysler-coupe-build.873/