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If your looking for a rebuilt engine Bob Powell from the Richmond, Virginia AACA has a rebuilt 288 from 1953. $5,000 Facebook Marketplace

I did the last thing I thought might be the source of the chirp/click (eliminated all exhaust leaks as demonstrated with the smoke machine) and it was still happening. I drove the car to do car chores on 2/8/25 (28 miles / 8 stops). When I was about a mile from my house I started to hear a very slight noise. When I got into my neighborhood it was worse. As I pulled into my driveway and parked in the garage is was really bad. I cut it off and opened the hood and smoke was billowing out of the oil fill. I think it must have been a wrist pin and not a rod bearing because it always had 45 pounds of oil at idle.

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Oh boy, sorry to hear this! (I forgot about all the discussion about your rebuild.)

Are you at the point that you're done working on this engine? I ask because whatever the issue is, it should now be easier to find. I'm not sure that a bad wrist pin bushing would cause billowing smoke.

If you were inclined, you could pull the pistons and maybe find the source of the problem. Whatever caused the billowing smoke and noise should be more obvious now. You would at least know exactly what you're dealing with and what the next best step would be. "If" is was a wrist pin bushing, that would be relatively easy to correct. If it was a rod bearing, that may be a different story as the crank may be damaged.

Neither of those would cause oil to get into the combustion chamber for smoke to occur. I can't think of an instance where something in the valve train would do that either. Only a broken ring or piston would do so.

I believe I mentioned before that my suspicion is that the noise is piston slap from a damaged piston, and that's still my best guess. As Don said, the only real way to get smoke into the crankcase is gases getting past either the valves or the pistons (rings) in great quantity, and for valves you would pretty much have to have a valve stuck open somehow, which I doubt.

I suppose another possibility is excessive ring clearance, damaging the lands and breaking rings. That would cause the same issue as well as tons of oil burnt into the exhaust.

Sorry to say you definitely will need to pull the pistons, but it might not be too bad to get the problem fixed overall. Just be sure to measure the various tolerances so you know it's good as it goes back together.

I agree with PGH, I think all would be revealed by pulling the pistons......hopefully!

Because the noise went from slight to significant in only a few minutes, it made me wonder if maybe a rod bearing spun causing it to lose lubrication and enough friction/heat to cause the crankcase smoke?

Maybe piston slap lead to piston failure?

Kunzea-Pull those pistons out and let us know what you find!

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I doubt it would be a bearing but I suppose it's a possibility. Sounds more like combustion smoke to me which would happen only in the combustion chamber, then getting pushed down through broken rings of piston. Of course, I don't recall that the noise was described very clearly and how it sounded would be a big clue in where to look.

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That would definitely tell you where the problem area is and can be done without removing the engine.

One day I went to visit a friend and a mile or two from the house my 1965 Cadillac Calais Coupe started making an awful noise. When I pulled up, my friend's mother was in the yard and I commented on the noise. She said, "Maybe it's that piece of cardboard stuck underneath!" It's too bad that not all noises a car makes are so east to fix.

HH56 makes a good point, as so often. In the neighboring city of Concord, CA, 122,000 inhabitants, here in the bustling, horrendously overpopulated East Bay Area, my now retired mechanic knew of only one (1) machine shop with a table long enough to check my inline eight Packard's cylinder head because they also still worked on old GMC 228/248/268 inline sixes.

If you can convince one or more of the shops you questioned that you have multiple large, long-established parts sources so they will never, ever be left hanging more than a couple days while the part being shipped, you'll find someone amenable to working on your engine. There are several older wrenches hereabouts who say they will no longer work on old cars because owners drop them or their engines off, expect the shop to spend hours, days, phoning around the nation. That's your job. Make it clear that there is absolutely no part on your car or engine that you cannot have immediately shipped after you make three or four or five or seven phone calls. Better still, print out the page(s) of their website/catalog showing such parts as he is likely to need.

BTW, several national parts vendors agree that USPS's' If It Fits It Ships boxes (several sizes) are far less expensive than Fed Ex or UPS, who've been raising their prices the last few years.