Example: a .50 caliber is 1/2 of an inch. Lets jus say a "1.00 caliber is a inch.
.44 = .44 of an inch or 44/100 of an inch.
Actually it is pretty well meaningless...the .44 magnum is .429 inches and the Ruger Old Army shoots .454 caliber bullets, and yet each is referred to as .44 caliber.So while the .44 in .44 magnum should indicate diameter, in actual point of fact, it does not.
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Nominally (not exactly) it is the diameter of the inside of the barrel of the firearm. A bullet that is roughly 0.44 inches fits the inside of the barrel.