Looks like it was undersized and someone attempted to shim it with
wood. That's a seriously shoddy design. I'd be tempted to pull the pin. Insert a milled
aluminum plug, then drill it for the pin. Other option, that could be done with everything in place, get a chunk of cushion foam, something you could squeeze past the pin, but would then fit snugly. Fill the top end of the rudder post with west systems
epoxy mixed with microballons. It would set up like stone, but be less brittle. You could add strand
fiberglass to the
epoxy if you wanted to take it a little further. That would keep the tube from crushing further. Those cracks shouldn't be there. It's hard to tell how big the gap between the black tube and the fiberglass portion is, but if you can get epoxy into it that would help. You can also use thin superglue ( hobby lobby or similar) and baking soda to make a very tough
adhesive filler. (Mind the fumes).