I found that the easiest way to cut a drainage hole in a tire is to use a punch made of galvanized pipe with a sharpened edge.
Grind down the edge on the pipe to a sharp angle, place the tire on a solid piece of wood (like a stump), set the pipe punch on the inside of the tire, give it 2-3 sharp blows with a hammer, and you have a large hole that will keep draining the water no matter what junk gets in it.
Grind down the edge on the pipe to a sharp angle, place the tire on a solid piece of wood (like a stump), set the pipe punch on the inside of the tire, give it 2-3 sharp blows with a hammer, and you have a large hole that will keep draining the water no matter what junk gets in it.