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Old 03-31-2016, 10:51 AM
Yosemite Sam Yosemite Sam is offline
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Join Date: Mar 2009
Location: Medora, IL
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Judging from the first picture you posted, it looks like the pulley is sloppy on the shaft and the key-way could be worn so close to the threaded hole that the bolt may not hold. If you clean the shaft up well, you may find that it is cracked between the key-way and the hole.

You might try putting the pulley on a different spindle to see how badly worn the bore is.

If by some miracle the shaft and the pulley bore aren't wore out, you can have a new key-way machined in the shaft 180 degrees from the existing one. If not then you will probably need a new shaft and pulley.
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