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I have heard stories of GIs returning from World War II grinding off the points of full metal jacket .30-06 bullets and drilling them out a little, because there was no expanding bullet ammunition for deer or elk hunting available in the immediate postwar economy.
 
Yeah. The hazard there is the bullets were open base, so if you took enough off the point, firing could just push the core through the jacket and out, spraying all over and leaving the jacket stuck in the bore somewhere. The clue is that no hole appears in the target. I think I read of someone bulging a barrel by shooting a round into one of those stuck jackets.

For 44 Special, you could do a lot worse than just buying full wadcutters for it. They are "pre-expanded" as compared to 32 and some 38 caliber hollow points. I suppose you could also hollow out a wadcutter with an end-cutting ball-end mill and glue a soft round lead ball into it and see if that gets you some expansion. I'd figure the wadcutter was already adequate, and the light ones can be driven pretty fast. The 215-grain hollow base WC could be loaded backward and tested as a hollow point for modest velocities.

Years ago, I read of some tests done with sabots that took a 44 down to 38 and that got pretty impressive velocities and performance, but a quick search isn't turning up any commercially available sabots for this, so you'd have to roll your own on a lathe using Delrin stock or something similar.
 
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