Brown Sludge In Radiator and Oil turned Black

So i finally opened up the head and the only damage i could see on the gasket was the holes. Could this have made the car misfire and throw water

 

Let us see a pic of the gasket surface of the head...You should have done a compression test before pulling the head. That would have told you immediately if you had a gasket issue...

 

Looks good but holes look clogged. And you can see on the 5th cylinder it was dripping coolant in it. It was also very moist

 

Alot of times you can get coolant like that from when you removed the head.

 

Coolant entering cylinder will steam clean top of piston, I see no evidence of that happening...

 

Like he said normally you will see if it's leaking by the tops of the pistons, it doesn't look like it.alot of times old cars you have to run cleaner in oil and change it quite alot of times before it's clean,but you can also plug up the pickup.and coolant can get to a brown sludge and even after running strong cleaners and flushing it alot it can still be dirty,the inside of engine is all rust and corrosion and contaminate the .coolant.

 

Intresting but when i turned on the car it would spit liquid out the back. And it never ever used to do that, only on start up sometimes.

 

Then why was my engine misfiring and spiting liquid out the back even when it never did

 

If it's a little water coming out that's just part of a combustion engine. Look at any car and you'll see water coming out of tail pipe. A running rough can be all sorts of things. Did you do a compression test and also a leak down test? Alot of times you can see a bad head gasket with a coolant pressure gauge, you will see the compression on the gauges needle. A leak down test would have told you if it's a bad head gasket or rings or valves ,very important to diagnose a problem properly before just ripping and tearing it apart unless if you are doing a complete rebuild.and coolant in oil is milky not black and you will smell it in the exhaust, a really distinct smell.

 

Because the liquid wouldnt drip it would come out with the smoke of the exaust. Kinda like vapor but alot of it also the smoke was like a blackish color. And the carburator was adjusted before all of it so its not running rich. How can i check if a cylinder is bad with just the head off? Because the cylinder walls look fine.

 

Black smoke is not coolant.

 

Did the exhaust smell like maple syrup...If it did...Yeah coolant getting into the combustion chamber. Look for a clean pair of pistons, look for any chambers on the head that are clean too...These will be evidence of coolant getting into the chamber. from what you have shown so far...We dont see a head gasket issue. I think your issues are carb/ignition related. But...Since you pulled the head...May as well have it gone over by a good machine shop. Get a new head gasket...Put it back together...Do a proper compression/leak down test to rule out worn rings and worn out cyl bores. Not uncommon issues with these old sixes...Then diagnose the actual problem using the advice you will get here. Need to see the smoking gun to say..."Yup head gasket" Good luck...

 

You hit the nail on the head

 

Thanks since i have the head off im taking it to machine shop to give it a good clean and cut it if needed. If it wasnt the gasket i dont know what it could be. Better not be a actual cylinder problem

 

Have them true up the deck...Do a pressure test...Check all the valves/guides and seats...Definitely have them put new valve stem seals in it...