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