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If on the outside of the plug (you do not specify) it could be a valve cover gasket leak. If on the working end of the plug (where the spark occurs) assume that either the engine oil is seriously overfilled, worn rod bearings, worn rings, worn valve guides and seals(intake), worn cylinder bores, stuck or broken rings in pistons. Ok, to explain, if the sump is overfilled the crank can cause enough oil to be thrown around that the oil control rings on the pistions cannot be effective. Worn rod bearing throw more oil than the rings can deal with. Worn rings allow oil past them into the combustion chamber where it fouls the plugs. Intake valve guides can suck oil into the combustion chamber during the intake stroke (high vacuum condition). Cylinder bores that are out of round prevent the rings from sealing properly. If the engine has received POOR maintenance the rings could be broken or stuck from mung (technical term) buildup on the pistons. Run a compression check to see what the pressure is on all cylinders. Write the numbers down per cylinder. Add a teaspoon of oil to each cyliner and retest, write those results down. Compare results, increased pressure indicates ring problems, no increase indicates valve guide problems.

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Q: What does oil on your spark plugs represent?
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