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Thom,
That sort of thing happens all the time, even on the $10K milling machine I was using yesterday. As others have said, clean up the tapers. A good way to clean the taper on the press itself would be to turn on the motor and hit it with a scotchbrite pad. You want it as smooth as possible. Clean the inside taper of the chuck too. The taper relies on clean metal to metal contact to work. Then install the chuck. I usually give it a few taps with a dead blow hammer, just to be sure.
As to why it happened, well that's another topic. Lets just say a drill tries to draw itself into the metal it's cutting. I'd recommend a bit more downward pressure when drilling, to keep the chuck fully engaged with the spindle taper. If the pressure is too light, you'll have the problem you experienced tonight.
Jim
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