Solly's post inspired me to post the other side of the coin. What car have you sold back when that you are still kicking yourself for selling? Mine was a 1970 GTO JUDGE, orbit orange, 4 speed, 3.90:1 rear, RAM AIR III.

 

The cars in my signature - a '68 W-30 convertible, and a '70 W-30 convertible, both 4-speeds. I sold them to friends who still have them, so at least I have visitation... I'd really like to have my main high school car back as well - '68 442 automatic with most of the creature comfort options you could get. I miss cold A/C in my current Rallye...

 

I'm very happy with what I have but I do miss a car that even in the day you hardly saw. My1970 Buick Wildcat, two door with the 455. I can't tell you the last time I saw one. I actually had the chance to buy it back 25 years ago but I already had the W30, didn't make sense at the time but for a few grand I now wish I did.

 

i bought a 77 cutlass supreme in june of 77,bright red,1/2 vinyl in black,t-tops,black buckets console and all the rest of the creature anemities. sold it to my bro in law at the time,so i could buy our house. he traded in on some truck. i miss that cutty,seen it once in the early 80s, nothing since,i dont even have a picture of it

 

I know most people thought these were ugly, but it drove better and was quieter than any 65-67 442 I ever had.

 

I really wish that I had never sold my first car from High School. I grew up in Northern Oklahoma, and I was into cars since I was a toddler. I read everything I could, and I really loved 4-4-2s. Around 12-13 years old, there was a beautiful '66 4-4-2 convertible around the corner from my friend's house. I worked odd jobs (mowing lawns, etc.) and worked in a grocery store as soon as I was 14 to save up for a car. When I was 15 1/2, I started looking. There was a '66 4-4-2 Target red convertible with parchment interior for sale about two hours away in McAlester, and I had just enough saved to buy it. Oddly enough, it was the same car that I had fallen in love with at 12. The owner bought it from the guy in my hometown. It sat in our driveway, and I worked on it until I turned 16.

Although the car only had about 70K miles, it had a questionable 1968 Rocket 350. The original engine was long gone. The owner said that the original owner from Kansas blew up the engine long ago. A couple of months after getting my license, I busted a lifter on the 350 street racing. I found a 425 out of a '66 Starfire in an Oldsmobile-only salvage yard in Solider, KS. I bought that engine and paid a guy to rebuild it, not yet confident in my skills. We found that the engine had very little wear, so he just honed the cylinders, put in new rings and gaskets and installed the engine. It never ran well even on premium gas. It knocked and pinged like crazy. We later discovered that the head gaskets were half the thickness of the original, and that the compression was even higher. I found this out after shattering a piston street racing again.

The second time, I rebuilt the engine myself. I had the machine shop bore it .030, bought forged aluminum pistons, bought a hot Crane cam, had a different machine shop polish the insides of the heads adding some volume, ported and polished the heads, added a high performance oil pump and larger pan. The newly rebuilt 425 was about 9.5:1 compression, ran on pump gas and was super strong. I never lost a street race afterwards.

The downside of the convertible is that I had it broken into a few times. One time they even slashed the top. When I went off to college, I did not want to risk having the car broken into on campus, getting door dings or having the top slashed, so I bought a cheap pickup. After about a year, the pickup died, and I decided to sell the 4-4-2. I needed money for another vehicle and to help pay for college, so I sold it on a consignment lot to a guy from Kansas. I regretted it immediately, and I have kept my eye out for it ever since.

 

When I was 20 in 1969 I traded my 66 Chevelle 396/360 4 speed, buckets, red out, white in, low miles, even, for a 1962 Corvrtte, low miles, maroon, black interior, both tops, original everything, factory fuel injected car. Like most of the cars I have owned I didn't keep it long, made a few bucks and took a hot 55 chevy 4 speed 411 rear car and a pile of money. The Vette was a local car which I knew about for a long time but was sold to the original owners next door neighbor. The injection was on it and was fine when sold but the neighbors son goofed it up and sold the car. The next owner then took the injection off, got it running well and it came to me. The injection was available for me to buy but I didn't.
You know what that would be worth today, so looking back that is the one car I should have kept I guess. But I have owned hundreds since then so I don't really brood about the ones that came and went. It's been a blast but I'm basically done now, too old and broke down to keep up the pace.

 

My biggest regret was selling my 68 H/O.
I drove every day for 4 years and sold it to a guy that actually saw me driving it one day on the highway and made me an offer .

That was 35 years ago and I'm still pissed at myself.

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My biggest regret was selling my first '70 442 back in 1977. It was 1970 4-speed car with a custom black lacquer with metal flake paint job. Other than the paint job, car was all original and had black interior with bucket seats , 455 rocket, factory 4 on the floor (with no console), 3:42 posi rear. That car ran like a raped ape, quite often would get rubber out of all 4 gears. Biggest problem was the rear wheel hop from a dead start, even with the L60-14 rear tires; and I wasn't a fan of putting ladder bars on it . Had unexpected medical bills in 1977, so decided to sell it to get out of debt. Should have hung on to it, an all numbers matching 442 and the body was solid

 

My biggest regret was trading in my '69 4-4-2 (in my signature) for my "Sammy Hagar Red" '79 T/A with the Olds 403. Like in most of these stories, I was a teenager, 19 to be exact. Newly hired by Ma Bell. I had been hot rodding the 4-4-2 and spun a rod bearing. At the time it was easier to get a loan on a car than come up with cash for the repair, and I needed a DD for work. I got $1500 trade-in for the 4-4-2 toward the T/A, and went home with an $80/month payment. I thought I had it made! Four weeks after the deal, I'm driving the T/A down the boulevard, and I see my 4-4-2 in the back of the hot rod lot with my license tags still on it. They had bought it at auction from the dealership where I traded it in. The hot rod lot wanted only $600 for it!!! I could not come up with the money no matter who I begged from, and since I then had an auto loan for the T/A, no one would give this new 20-year old another car loan in tandem. The T/A was a blast, but, Damn I miss that 4-4-2!

 

i have 3 a 64 starfire conv,a 65 442 and a 68 ss427 impala.

 

Since I inspired Dragline I will provide my two wish I had them back vehicles, they may surprise you.
Like any other young man I enjoyed performance and speed, My speed/performance car was a 1957 Chevy sedan delivery, while this car was
street drivable it was set up for the strip or street racing ( and it was not a good handling car) so it was not a practical or economical veh. for everyday use plus it was a money pit and I was always fixing something.
Now I Was single in these days with a pretty decent job so I had the luxury of having another vehicle (plus a 1971 Triumph Bonneville) my daily driver was a 1969 2 door Chevy Impala 327 4bbl, Sea mist green with a black vinyl top I purchased from a retiring work associate. It rode like a dream and had decent performance it was clean as a hound's tooth and I loved that car.
I stepped up a bit on my next daily driver (I still had the 57) and bought a 1972 2 door Buick LeSabre chocolate brown with saddle brown interior and a white vinyl top what a excellent everyday cruiser it was !! so as strange as may seem those are two of the cars I would like to have back today. However its hard to beat cruisin my Olds !!

 

I regretted donating my 74 Cutlass Supreme to charity for a tax write off and wound up getting a 93 Pontiac Bonneville with a supercharger. Worst car I ever own. I even called the charity company that I want to buy my 74 Olds back but it was too late. They said the car is already driven away on a flatbed.

 

I have mourned the day I sold my 66 Cutlass. Purchased new March 66. Convertible, Lucerne Mist, blue interior, blue top, 330/320, P/S, PB, 4-speed w/console, min slip, dual exhaust and radio. Have never forgotten that car. Sold in 70. Bought a 70 Cutlass Holiday Coupe for the family. No Oldsmobiles until I bought another 66 Cutlass Vert in 2016 this time Target Red and factory 4-speed. Equiped pretty much like the first one.

 

Great thread!! My first car was a 1965 GTO, (purchased 1968) factory air, 4 speed with a console, factory tri-power, convertible. Red, white convertible top and red bucket seats. . Everyone loved the car except me. The car handled like a boat. I never liked the car..........sold the car for, at most, $900.00!! (1970)

We, my father and I, then looked to buy my friend's 1968 Corvette, L-88, factory sidepipe, triple black,convertible. My friend was asking $6000.00, and the car was beautiful. My friend started the car and my father said the car "sounds like it was missing and needed a tune up badly." (The L-88 cam was radical) We then went for a test drive, with the top down, and it was over. My father was not letting me spend my money on a '68 Corvette, especially with NO AIR and NO RADIO, that also needed a tune!! I was upset, but looking back, it was funny to see that my father was looking out for my interest. (1970).

We went to the Oldsmobile Dealer, and I ordered a 1970 442 convertible with automatic. My father liked the value and the looks of the W-30 package, approximately $270.00, so I ordered the W-30. The salesman continued down the order sheet and came to Four Seasons Air Conditioning, price $475.00. No way I wanted air conditioning, because I knew air would slow the car down and I planned to race. I tried everything to convince my father, who was insisting that I buy air, that "air wasn't needed and expensive........ dad the car is a convertible, I can open the windows and the vents to bring in ambient air, even in the rain." No way my father was going for my B/S so he told the salesman that HE was paying for the air conditioning.

I loved the 442, and to this day, the 442 has always been my favorite car.

Waiting for Fred to sell me one of his 442 convertibles or Stevengerard to sell me his 442 convertible.

 

71 Coupe DeVille

 

[QUOTE=twilightblue28A;1275280]Great thread!! My first car was a 1965 GTO, (purchased 1968) factory air, 4 speed with a console, factory tri-power, convertible. Red, white convertible top and red bucket seats. . Everyone loved the car except me. The car handled like a boat. I never liked the car..........sold the car for, at most, $900.00!! (1970)

I had a 65 Tempest White 2 door, 326, power slide trans, had red interior (bench seat) I loved the car hated the interior ! I had a ex shop teacher that had his 65 GTO stolen and totaled,He bought the car back from the insurance co. and proceeded to part it out, I snapped up the interior (black) and badging and transferred it to the Tempest. Then that was called a GTO wanna be !! now it's called a Tribute car !!
any way the biggest part of the job was painting my red interior trim to black otherwise a slam dunk. now my car was a column shift and his was a 4 speed with a console, I just kinda used the shifter hole as a cup holder for my Micky D's Cokes.
P/S I don't remember that car handling like a boat I thought it had good road manners.