I just had a thought! (surprise!) Maybe previous owner installed a pre 1965 starter with the long starter drive and the torque converter housing will not accomodate it. That might jam the end of the starter drive between the flywheel and the housing. My guess would be that you would need to seperate the converter housing from the block to fix the problem. Don't know if you can do that! Oh, yeah - you can leave the torque converter attached to the flywheel - no, maybe not. I'll keep thinking about this... Art??
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