I agree with Gary, chances are the stainless bolts are welded to the aluminum due to galvanic corrosion. This was the case for my quadrant, two bolts came out with a lot of gentle persuasion, but the other two snapped off and had to be carefully drilled out of the aluminum. Maybe Joshs quadrant was previously removed or maybe he is not in salt water? Once I got the holes drilled out, I drilled them straight through and bolted through with longer bolts and nylon lock nuts. Also used tef-gel to prevent further corrosion. The rudder weighs at least 100lbs. If your rudder post is like mine, there is a ½ threaded hole in the top; I threaded in a long ½ rod, ran it through a piece of hardwood, installed washers and nuts to lower and later raise the rudder into place.
Mike Amirault C&C33ii Lovely Cruise SMSC
_______________________________________________ Thanks everyone for supporting this list with your contributions. Each and every one is greatly appreciated. If you want to support the list - use PayPal to send contribution -- https://www.paypal.me/stumurray