It sounds like the boat is still in the water. Please confirm. I also assume emergency post, quadrant all all bolts are removed from the rudder post.
If so (and I hate to say it), using the the boat's weight or momentum as force to pull the rudder out may actually be exacerbating the problem, as this could contribute to the bending of the rudder post, or worse, break your shaft housing tube integrated to your hull.
I had to take my rudder on and off the boat multiple times while it was on the hard for a variety or reasons (mainly fairing and fitting of the rudder stub to the rudder after I relaminated that section of the hull), and it is no easy task even with a brand new rudder. It could be that the lower bearing has worn a slight groove in the post that is caught on the bearing (my old rudder had such signs), where careful positioning and alignment of rudder would allow it to free up and then drop. Or it could be the PO did something whacky to insure the rudder would not fall out accidentally.
If you have to get the rudder out, the boat is still in the water, and it won't budge, you may need to haul it and attempt it again with better access. It may be as simple as just finessing the rudder so it can slide out (which you can do with a mask and snorkel first), or doing some exploratory surgury by cutting in to the shaft housing tube for further inspection.
Good luck!