My very first question on reading this was: What caused the cracks to happen?
The pulley is cast iron no?
This tapered pin is...... ?
If it is tapered, is the fattest diameter of the pin bigger than the hole? Could it have been tightened enough to initiate cracking?
I don't think all these radial cracks suggest overloading of the pulley shaft or relative movement between the pulley and shaft. However, they could be formed by overtightening the tapered pin.
I think the reason for a tapered pin is to take up all the clearance in the hole so that the pulley cannot move relative to the drive shaft. Likely, the first design was a straight pin. That was changed to a tapered pin when the hole started to wear from relative movement of the pulley and shaft.
But I'd bet there was a tightening spec on that pin. Either for driving or torque.
I think those cracks are from overtightening the pin - either driving it or torquing it.
I'd favour an exact fit shear pin over a tapered pin.
I also like
@Darren's collar idea. But when you make the collar keep in mind that these cracks are likely caused by the pin not by the shaft load. So the collar should be installed and tightened before the pin.
I don't think brazing or welding will help. The expansion caused by the pin must be dealt with or it will just crack elsewhere.
Do you have an owners or Service Manual for that machine? If so, look up that pin and the install procedure.
I could also be all wet. But those are my thoughts on it without the benefit of being there.