Re: Square Holes
 

Gary,

You would likely be fine doing that with small cutters and plastics.

I don't think I would try it on metals. The spindle bearings in a drill press are intended for axial load only and would likely wear out very quickly with the radial loads you would see in milling metals.

Furthermore most drill presses are going to have the chuck held in place passively via a Morse taper. This is going to be your biggest problem as side loading such a setup can cause the chuck to break loose from the taper. This would be bad news.