Older 11-100 Delta drill press

That is correct and the bearing has no effect on the gear shaft. When I took it apart all I did was add grease to the gear and WD-40 to the shaft.

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The way it appears to me, the gear shaft is supposed to drop when the drill press is still running but in neutral. I'm trying to find out why it won't stay in gear.

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I was able to solve my problem. After assembling the pulley and before installing it, there is a small metal cap that needs to be mounted on the pulley shaft. This cap, when securely mounted, provides enough friction to keep the gear in gear.

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