I recently got a 2003 or 4 mud buddy longtail. I was looking at the upper bearing assembly and wasnt sure if this looked right. To me it looks like it needs pushed down in but wasnt sure. I looked at many pictures and this one looks different as if the bearing has been pushed out. I know the u-joint set screw is out, I was tightening them when I noticed the bearing assembly. So, Is the bearing assembly suppose to look that way?
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No, it needs to be pushed in. loosen set screws, remove zerk and gently tap it back in, ( I use a wooden block), tighten set screws, add some grease especially if none came out.

when you start it up and run it check for heat at the upper bearing, if it's hot something is wrong. Odds are good it'll be in your U joint.