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 - New Hitches For Your Old Tractor - by Chris Pratt. For this article, we are going to make the irrational and unlikely assumption that you purchased an older tractor that is in tip top shape and needs no immediate repairs other than an oil change and a good bath. To the newcomer planning to restore the machine, this means you have everything you need for the moment (something to sit in the shop and just look at for awhile while you read the books). To the newcomer that wants to get out and use the machine for field work, you may have already hit a major roadblock. That is the dreaded "proprietary hitch". With the exception of the
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