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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