Original Paint: 1957 Pontiac Chieftain

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The “one owner, little old lady, only driven on Sundays” stereotype is well-worn, and many treat the concept with a grain of salt. However, those are the claims made by the seller about this 1957 Pontiac Chieftain. It wears its original paint and has 58,000 miles on the clock. That leaves its new owner with decisions to make. It is ripe for restoration, although preservation is a valid option. It needs a new home, with the seller listing it here on eBay in Woodstock, Connecticut. Bidding sits below the reserve at $5,555, but there is still time for interested parties to throw their hat into the ring.

The seller claims this is a one-owner classic, although they would technically be its second owner. It is unclear when they purchased the Pontiac, but they indicate it led a sheltered life. It wears its original paint combination of Carib Coral and Kenya Ivory, with no history of restoration or repairs. The paint is tired and sports surface corrosion, but preparing the vehicle for a cosmetic refresh shouldn’t cause many headaches. Its original owner rarely drove the Chieftain, only using it in stereotypical “little old lady” fashion on Sundays. It spent its downtime in a dry garage, making its lack of penetrating rust unsurprising. The seller identifies a single spot in front of the passenger-side rear wheel well as the only area of steel penetration. The remaining panels are clean, with the floors and frame in a similar state. Although restoration would seem the obvious path, preservation has its attractions. Treating the corrosion to prevent further deterioration would allow this Chieftain to wear its survivor badge proudly. The trim looks acceptable if the buyer selects that path and there are no glass issues.

Pontiac released its Second Generation Chieftain in 1955, with the car remaining on sale for three model years. It underwent cosmetic updates during that time, but the mechanical specifications drew the most attention. Pontiac brought its first OHV V8 to the table in 1955 with a capacity of 287.2ci. It increased its capacity in 1956 and again in 1957. This Chieftain features the 347 that sends 252hp to the road via a four-speed Hydramatic transmission. The original owner added power assistance for the steering and brakes to provide the effortless driving experience that many little old ladies might expect. Pontiac didn’t market the Chieftain as a high-performance model, but its ability to gallop through the ¼-mile in 17.3 seconds on its way to 114mph demonstrated it was no automotive slug. The seller indicates there are no mechanical issues with this classic. They say it runs and drives as it did the day it rolled off the showroom floor. I wouldn’t be surprised if it is actually better because the new Vision Wheels Legend 5 alloy wheels and radial tires should improve the comfort and handling while providing excellent cooling for the recent front disc brake upgrade. If the new owner craves originality, reversing those changes should be straightforward. If I owned this classic, I would probably source the parts and squirrel them away. That way, they’d be on hand for a faithful restoration, or they could be a bonus for potential buyers if I chose to place the car on the market.

This Pontiac’s interior will divide opinions because it is another aspect offering a world of possibilities. Some painted surfaces exhibit deterioration, although the dash and bright trim are excellent. The headliner should benefit from a careful cleaning, with the same true of the door and rear passenger compartment trims. The carpet is toast, meaning a replacement set would lighten the winning bidder’s wallet by $260. The wheel is badly cracked, and sourcing a new one would be the logical choice. The seats are mismatched, which is the most significant hurdle facing the new owner. Sourcing replacement covers would cost approximately $650 but should dramatically transform the appearance. Therefore, this interior could look pretty impressive with some careful cleaning, painting, and around $910 spent on replacement parts.

This 1958 Pontiac Chieftain leaves me torn because I can’t decide which path I’d choose if it were parked in my workshop. Restoring it to a factory-fresh state is viable because the new owner doesn’t face a mountain of rust repairs during that process. However, addressing its single rust spot and preserving the car is a second option. I would probably compromise by leaving the exterior untouched but returning the interior to its former glory. That would provide a striking contrast guaranteed to draw crowds. Those are my thoughts, but what would you do?

Auctions Ending Soon


  1. CadmanlsMember

    Hate me, I have always thought a 55-57 Poncho built with real Pontiac power would be the way to go. Dimensions very similar to the tri-five Chevys and you never see them. Yeah I like Pontiacs. The wheels are a great start, suspension, brakes and a Butler performance crate engine, modern transmission and amaze people and be a hoot to drive and own. This is a solid looking car to build, too bad I am getting too old to take it on.

    Like 24
  2. Joe Haska

    If the reserve is not too high this could be a very good buy. As the author says the interior could be brought back for under a $1,000 and well worth it.
    This would make a very nice drver quality car.

    Like 12
  3. eyes4color62@gmail.com CooterMember

    I love these and never see one any more. Please, someone buy this, restore back to original colors, replate chrome, perform the necessary upgrades to interior and get the original rims, hubcaps and wide whitewalls back on this beauty. You have a very rare, numbers matching classic here that will be a jewel of a head turner if done right.

    Like 24
  4. Yblocker

    Well first, this brings back some good ole memories. In 1977, I bought a 57 Chieftain 2dr, the same 347, w/3spd manual, all original, straight as an arrow, rubber floor mat, manual steering and brakes, factory radio, which still worked, beautiful car, all for $250. Friends all told me I bought a “pig in a poke”, paid way too much for a 20 year old car. If still had it, I’d sure as hell get the last laugh. And I do, wish I still had it. As far as this one, if I had it, I’d have to clone the one I had.

    Like 8
    • Yblocker

      Something I noticed on this one, is the awkward mounting of the generator on top of the engine, I’m guessing it’s due to the addition power steering, looks pretty crapy, glad mine was manual. Radio delete seems unusual too, for an original buyer to order carpet, and power steering and brakes. For those who didn’t know, the radio speaker, was a pretty big speaker, mounted on the floor, up under the dash.

      Like 2
  5. Jerry Bramlett

    The seller is a dealership, Wootton’s Redline Classic Cars. This ’57 is listed on their website for $19,995. I don’t know the reserve in the eBay auction, but I’m guessing it might be close to that much.

    I’m the high bidder now. I would install a Borg Warner 4-speed with a ’62 Chevy spaghetti shifter and a ’58 Pontiac Rochester FI set-up that I already own. I’m not holding my breath. The car isn’t worth ~$20,000 to me. I’d have way too much in it after making my “improvements”.

    Like 9
    • James

      $10K or $20K, life is short and it’ll be a long, long time when another like this comes along. Bite the bullet and make it happen. Would be great as a 4-speed fuelie.

      Like 0
  6. Michael Berkemeier

    Way cooler and way better looking than a boring ’57 Chevy.

    Like 13
    • Dave

      Yes, so much more interesting than a Chevy. I can’t say that I’ve never seen one at a car show, but if I had it was damn few.

      Like 2
  7. Denny N.Member

    Seller was wise to convert to front disc brakes. The standard drum non-powered brakes on these Chieftains were downright scary!

    Like 2
    • Yblocker

      Oh bull pucky, I owned and drove many 50s cars and trucks, the brakes worked just fine. Geez

      Like 10
      • Chris

        You are correct Yblocker. The old drum brakes stopped those relatively heavy cars in a reasonable distance for decades. Younger guys that didn’t live with manual drum brakes just don’t understand that if you use a little effort the car will stop without any shenanigans. This one has power assist so it wouldn’t have even require the owner to work hard…

        Like 5
  8. DON

    There’s a 2 door hardtop 57 in the background in one of the shots ; it doesn’t look as good as this one though

    Like 1
  9. Racer-X

    Paint overspray in the vin tag and door seal.
    I really regret selling my 57 tripower Chieftain.

    Like 1
  10. J. Kezlaw

    Had a 55 2dr post , solid car , rebuilt the engine in vocational school ( Dobbins Philly. Pa. ) . New rings bearings gaskets , two new lifters , perfect circle valve seals and found a four barrel carb. & manifold in the junk yard ($ 15.00 ) . Neighbor wrecked a 56 w/duals exh. ,that went on my 55 quick . It was a great learning experience & fun car !

    Like 7
  11. eyes4color62@gmail.com CooterMember

    C’mon guys, let’s not church it up too much. It’s a nice old car but there are several reasons the 57 Chevy is an iconic vehicle. And YBlocker, you’re spot on about vehicles from the 50’s, they drive just fine if you know how to drive!

    Like 9
    • kkarl

      Iconic , yes, but so were Marlboro cigarettes and Budweiser .When someone says beer, people think Bud, name a classic car, many people would say 57 Chevy. All of these products sold like hotcakes, but there were so many better offerings ….

      Like 5
  12. Poncho

    I like this car. I was born and raised close to Lebanon, PA. I used to cruise the Circuit and hang out occasionally at Coleman Park back in the 80’s and 90’s. I’ve been thinking about buying one and fixing it up for mom to drive for a while since she loves the 57 chevy, but i am more into Pontiacs. This may take care of both of our wishes. Sadly, the buy in price at $20k is beyond my reality budget. It would have been great to bring this car back to it’s home town of Lebanon and have it hit the streets again. Mom would have had a big smile.

    Like 1

    I had a 57 Chieftan 2 door HT back in the day. Kept th3 347, Isky solid cam, tri power, Vitar hydro. Them poor GTO owners didn’t know what hit em. Broke one rod and twiated the one next to it 90 degrees. The broken one took huge chunks out of the block swinging around on the crank. OUCH. Sure miss that car.

    Like 4
  14. Mark

    Very cool car. Not saying I wouldn’t rather have a 55 Chevy but a nice looking old floater.

    Like 0
  15. Glenn Hilpert

    Only 21,343 were made. How many left? My guess around 21. I miss my former Poncho’s. A 55 Starchief Ambulance, 58 Starchief 2-dr H/T, 60 Ventura 2-dr H/T, 67 Catalina 2-dr sedan, 69 Grand Prix and a 69 Lemans with a factory 4-spd. Great memories. This one appears decent with good bones and hopefully whom ever buys at a reasonable price, will restore back to original including those Dog-dish caps.

    Like 2
    • Poncho

      At $20k reserve, there goes the reasonable price theory out the window. New interior kitas article authour points out would be $1000. but if you want a fresh repaint, add that (probably at least $5k), the chrome plating…yeah, if you paint it, you’re gonna want the jewelry to shine like a diamond in a goat’s butt. Price chrome plating lately?

      Like 1
  16. Norman "Pete" McGill

    I’d fix the paint and the interior, rechrome ALL the chrome and hang a fully extended continental kit on the back. Maybe twin spot lights, skirts, dual radio antennas, rumbly mufflers and you know the rest. Then drive the wheels off it and sell it for what I have in it. Ya, that would work. I really love the 57 Pontiacs and especially the convertibles. 58 wasn’t bad either.

    Like 2
  17. Pete Phillips

    Get rid of those awful after-market wheels! Compound and wax the paint and I think it will look so much better. Does anybody keep old cars original anymore? I see the wrong valve covers, the wrong air cleaner, orange spark plug wires, and the wrong front seat, in addition to those wheels. Yes, I’m a purist and to me this car just screams to be put back to original condition.

    Like 4
  18. T. MannMember

    4 speed hydromatic in 1957?

    Turbo-Hydramatic is the registered tradename for a family of automatic transmissions developed and produced by General Motors. These transmissions mate a three-element turbine torque converter to a Simpson planetary geartrain, providing three forward speeds plus reverse…

    Did seller lie, or add an overdrive???

    Like 1
    • Norman K Wrensch

      The three speed turbo hydramatic did not come into existence until 1964 in the Buicks and 1965 for the rest of GM. Before that most Hydramatics starting in 1940 where four speeds and used a fluid coupling, not a torque converter which is why they where four speeds to make up for not having the torque multiplication from the torque converter. And from 57 up they used two fluid couplings, which was discontinued in 1965. They did not have overdrive.

      Like 1
  19. pwtiger

    Hydromatics were available in the 40’s, my 49 Caddy has one, I’ve seen mid 50’s GMC pickups with the 347 Pontiac engine and a 4 speed Hydro.

    Like 1
    • Jerry Bramlett

      You’re correct. Olds was the first just before WWII, and all GM divisions had them shortly thereafter. Hydra-Matics had four forward speeds. Turbo-Hydramatics had three.

      Like 0
      • Yblocker

        I had a 59 Cadillac in high-school, it started out in 1st, shifted to 2nd, and then to 3rd, never noticed 4th. Did I miss something? I’ve always wondered about the 4spd hydro-matic, but never quite understood. Enlighten me please

        Like 0
      • Jerry Bramlett

        From 1956 to 1964 Cadillac used a Dual-Coupling Hyrdra-Matic transmission they called a “315”. Other GM makes had their own trade names for it, such as “Jetaway” with Olds. It had four forward speeds and two “Drive” ranges. The driver got to select either range.

        One “Drive” range held the transmission in 3rd gear until the maximum shift rpm was reached. In other words you had to be going very fast in 3rd before the transmission would shift into 4th.

        The other Drive range shifted into 4th in regular fashion at relatively low speeds. I’m not sure how the two Drive choices were displayed on the dash indicator… maybe D1 and D2… I just don’t know.

        Like 1
  20. Yblocker

    Well, it’s been 50 years since I had that Cadillac, let’s see, I got it in 1973, I was 16 years old, I’m 66 now, yup, 50 years ago, damn how time flies. But if I remember right, the quadrant was Park N D L R.

    Like 0
  21. Poncho

    Lets see, a (Coral -pink colored) ’57 Pontiac Chieftain with a v8 for $20k or a light blue ’57 Chevy 210 with a inline 6 cylinder for $24k. Pretty tough call, but I think the Chevy has the desirability hands down not to mention ease of sourcing replacement parts. This hobby would be more popular and more cars would be on the road getting driven if people were realistic about their asking prices. I am one that doesn’t like to haggle. Tell me your “I gotta have this much price” and I will make the decision to buy or not. I know…any car is what someone is willing to pay and everyone wants to get as much as they can, but c’mon man.

    Like 1
    • Jerry Bramlett

      I couldn’t agree more.

      In the past I’ve politely told sellers that I don’t haggle, but I’d like to buy their part or car. I then ask them their price. Sometimes it’s okay, and I pay it. But often, it’s more than I’m willing to pay. I then tell sellers “no thanks”, but I appreciate them talking to me.

      Many sellers seem bewildered by this approach. Some don’t believe me and keep trying to “negotiate”. Go figure.

      Like 1
  22. Lowell Peterson

    Predator resellers that can’t live with a reasonable markup are the single worst aspect of the old car hobby. They settle for 3-5% on moms 401k but they want 150% for the barn find? Total predator!!!

    Like 0

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