I've seen two deer killed at fifty-some yards with an 1851 Navy ( two different deer on two different occasions, mind you). One ran about a hundred yards before falling down. As the hunter approached it got up and went another twenty yards or so then dropped. The other one was a lucky shot that went straight into the does chest and she didn't go very far. During butchering/autopsy it was found that the bullet had passed through the lower tip of the heart.
Heck, at 75 yards a round ball or conical from a .36 Navy would probably have about as much energy as a .32 long at the muzzle, not to mention some of the various small-caliber loadings used in a number of military pistols as used by different European nations in the earlier 20th. century. The .32 long at one time enjoyed a great deal of popularity in law enforcement circles, especially among detectives and plains-clothes officers.
Who knows? Some men have died from a single shot from a .22 short while others have taken several rounds from a .357 magnum.
Oh, and for those would-be scoffers of a Navy killing a deer at 50 yards, do a little research on what the most popular cartridge is for deer poaching. That's right, it's the "lowly" old .22 rimfire.