craftsman 150 drill press

that looks just like the set up on my WT drill press. The idea is that unscrewing that collar should force the chuck off the male taper which is part of the spindle. That didn't work so well for me as I don't think it had been removed for ~60 years, so I made a couple of tapered wedges (easier to buy them, but I was too tight):

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and then either used a C-clamp or a small drill press vise to squeeze them together between the chuck and the collar. Took a scary amount of force, but it popped off. Now it's easy to use the collar, which also retains a Craftsman collet chuck that George Wilson gave me for "milling".
 
if the oiling and c-clip doesn't work I have a bearing splitter I may try, same as your wedges but with 5/8 bolts and nuts that should give enough force to remove it, at least I hope it will :thinking:
 
After seeing the pics it looks like you have the collar which is used to removed the chuck. Put a spanner wrench on it and start turning, it should pop the chuck off.
 
Look between the quill face and the chuck. If the tapered arbor has a step, you can insert a drift between the arbor step and the quill and give it a rap with a hammer.

my DP has the same chuck.
mine won't come off either
spanner, pickle forks, bearing splitters......tried all that. Now I am going to heat it and smack it
i may also just leave the collar loose and just use it until it falls off
 
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