How to grease this wheel?

Oops! That’s not a greasable bearing, those are oil bath bearings. They need be torn down and all the grease needs to be washed out. Then reassemble it all and fill the hub with Hub Oil to the level of the hole in the middle. YouTube or Google can help with how to fill them, or I can try to explain. But first thing is to get all that grease out of there!

That “pin hole” in the middle is not a hole either, it’s a cone-shaped indentation that was used by one end of the lathe that machined the axle shaft.
 
Oops! That’s not a greasable bearing, those are oil bath bearings. They need be torn down and all the grease needs to be washed out. Then reassemble it all and fill the hub with Hub Oil to the level of the hole in the middle. YouTube or Google can help with how to fill them, or I can try to explain. But first thing is to get all that grease out of there!

That “pin hole” in the middle is not a hole either, it’s a cone-shaped indentation that was used by one end of the lathe that machined the axle shaft.
Reach, thanks for this info! I didn't realize these bearings aren't greasable. I've only had the chipper a year, and tow it about 20 miles per day on average, so maybe I've got some time before they need to be torn down and re-packed?
I'm missing one of the dust caps, so another thing I need to do is track down some spares...
 
Reach, thanks for this info! I didn't realize these bearings aren't greasable. I've only had the chipper a year, and tow it about 20 miles per day on average, so maybe I've got some time before they need to be torn down and re-packed?
I'm missing one of the dust caps, so another thing I need to do is track down some spares...
You’re welcome! And now you know. Question is, when were they packed with grease, right before you bought it, or five years ago? 20 miles a day is still about 6k miles a year.

Personally, I would clean them and oil them properly now. You could call a good local trailer shop, they might be able to give you a better idea how long you can safely go before you need to have them fixed.
 

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