Does his tractor have the inspection plate that can be removed and then maybe see what is going on? I.e. oil from main or trans?
 
For the perfect cure, I suggest that you replace the clutch disc, re-face the flywheel, repair, replace or adjust the pressure plate and replace the throwout and pilot bearings. You cannot do a clutch repair half_axxed or you will be disappointed. And who wants to do the job over? Used a genuine JD clutch disc because the so-called finger-type clutch discs can grab and ruin the flywheel and pressure plate surfaces.
 
You have oil on the disc. Same deal as when u have a leaking rear wheel seal on a truck that brake will grab and skid.
 
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