Typically, the cast iron bearing housing has worn a bit allowing dirt to sneak in between the spherical OD bearing and the housing and clog the groove in the bearing where the grease is supposed to flow to the tiny hole in the outer race of the bearing.
If you get rough and follow the advice in some of the other replies and get grease to flow to the bearing, you will inject all the dirt/crud that's in the groove into the bearing along with the grease.
At this point, I would quit trying to grease it and watch it/use it up, then replace the bearing and housing.
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Today's Featured Article - Third Brush Generators - by Chris Pratt. While I love straightening sheet metal, cleaning, and painting old tractors, I use every excuse to avoid working on the on the electrics. I find the whole process sheer mystery. I have picked up and attempted to read every auto and farm electrics book with no improvement in the situation. They all seem to start with a chapter entitled "Theory of Electricity". After a few paragraphs I usually close the book and go back to banging out dents. A good friend and I were recently discussing our tractor electrical systems when he stated "I figure it all comes back to applying Ohms Law". At this point
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