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I'm looking for some advise on my rudder.
There is not much play in the wheel, or the rudder itself. There is a pillow block bearing near the top of the post that looks like it needs to be replaced. I think that the a soft rubber bushing part is all that needs replacing. The sleeve part that has a set screw and connects to post cant come off the top because the key way above it. So would I replace the outer housing and pillow part by taking the quadrant off the top? Also, everything is quite rusty... And overall I'm not to familiar how it all works. I believe that where the stock going into the tube is a type of stuffing box, doesnt look great to me. any tips are helpful. Losing steerage is one of the top 3 scariest things!

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I'm not sure what is going on there. Pillow block bearings do not have rubber inserts. It looks like someone may have replaced the bearing insert with the wrong type, which would explain why the rubber has just fallen out.

I would replace the entire pillow block bearing assembly rather than just parts of it. They are really quite cheap. Stuffing a other piece of rubber in that doesn't belong there isn't going to solve anything.

In order to replace the bearing you will need to first remove the quadrant. Judging by the amount of rust it is likely going to be a challenge, but it should come off with the help of a good gear puller, lots of penetrating oil, and perhaps a torch to heat it up.

Once you are down to the bearing you can either is the same puller technique, or you can carefully cut the bearing off using an angle grinder, being careful not to nick the shaft. Then just clean the shaft really really well with emery cloth. If the bearing does not slide onto the shaft easily, don't force it, clean the shaft more.

I have replaced plenty of pillow block bearings on shafts that look worse than that, so it is doable. You just need to have the right tools.

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