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The Drill Press in question is a Wen 4214. I had originally seated the chuck by tapping it with a hammer by way of a piece of scrap and then, for good measure, pressed it into a piece of scrap. It's been working great!

But, I had need to drill a big hole...a 4.5" hole to be exact. I attempted to drill slowly, but apparently wasn't careful enough and got the bit stuck. When I released pressure to bring it back up, the bit immediately started to wobble. I cut power and the chuck completely fell out.

I planned on cleaning up the taper and reseating but noticed some chipping on the tenon (imaged below). Because this is such a precisely machined part, is this chipping basically junking my chuck?

To summarize my main question: Is the chuck irreparably damaged?

Secondary Ask: Any advice you have on the chuck coming out using a hole saw bit is welcome.

images linked to larger versions

That is a Morris taper. Clean it off and slip it back in place a light tap with a mallet should seat it. The tail stock on my lathe has a MT4 much larger and I have spun it out several times, I wipe it down with brake cleaner inside and out and slide it back in then a tap and it is fine. I have a fly cutter that is about 5" and I use it all the time on the mill I use light pressure and don't usually have any problems. Your drill bit probably grabbed and sucked down breaking the connection. Don't drive it in hard or you may deform the mandrel.

Large hole saws can cause problems with drill presses. I read somewhere that Jet doesn't recommend using them at all. One problem is that most woodworking drill presses can't be run slow enough for a tool with that diameter.

Regarding your chuck ... tough to tell. I'd take a fine file and clean up any burrs or rough spots on the mating surfaces. Stick your finger up inside the quill on the press and see if there are any rough spots there. If so, you may need to get a reamer to clean it up. Clean both surfaces with a no-residue solvent - acetone, carb cleaner or such. Then put the chuck back in, put a board under it and use the handle to press the chuck back into the quill. Or tap it up with a plastic or wooden mallet.

Good luck. I've had this happen twice. Once with a small Delta benchtop unit. Never could get the chuck to stay in again. The other on a bigger craftsman - so far it's held despite a fair bit of abuse.